[読みたい論文] 光学活性アミンの絶対配置と光学純度をシッフ塩基にして決めます

Viewed: 13:25:35 in December 16, 2019

Posted: July 11, 2019

Predictive chirality sensing via Schiff base formation (Pilicer, Samantha L.; Mancinelli, Michele; Mazzanti, Andrea; Wolf, Christian)
Org. Biomol. Chem. 2019, 17 (27), 6699−6705.

Keywords: Schiff base; circular dichroism; enantiomeric excess


不斉中心を持つ光学活性アミンの絶対配置と光学純度の新規な決定法について報告している論文のようです。

光学活性アミンの絶対配置の決定方法には色々あって、最も確実な方法の一つに結晶化してX線解析するというのがあるのですが、この方法、アミンが液体だとまず無理なのです。なぜ無理かというと、アミン分子が色々な意味で動きまくるからです。色々な意味というのは、分子そのものが移動したり、分子中の単結合が回転したり、などなど。その対策、つまり、アミン分子そのものの動きを止めるために、アミンと何かを反応させて結晶化させる方法が取られてます。

この論文ですが、結晶化による絶対配置の決定のためにもですが、同時に光学活性絡みの何か他の測定法にもという一石二鳥も狙ったのが、この論文の趣旨のような気がします。その手法として、何かを反応させて分子構造を混み混みにしたった、ということなのでしょう。分子中の単結合の回転により取りうる配座を制限して、光物性が「きっちり」出るようにした、そしたら光学純度をCDスペクトルとかで決められるぞと。

目論見どおりの結果が出たのか知りたいので、読みたい論文に追加です。p-ブロモベンズアミド化とか結晶化させるための反応は色々知られてるし、わざわざこんなことせんでもとは思いましたが、派生する何かがありそうな気もしますので。

この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
twitterアカウントは@makiokafufudo(お仕事用)、@ymakioka(個人用)です。

 

1940年はこんな年

人名反応など
Baudisch反応 [Doi 1]
Carroll転位 [Doi 1]
Cope転位 [Doi 1]
Kroll法Ramberg−Bäcklund反応
ノーベル化学賞
(該当者なし)

できごと
炭素14をMartin KamenとSam Rubenが発見
米国・科学者動員令1940
日本ニュース映画社(日本映画社)設立
武田化成株式会社(吉富製薬)設立
大阪朝日新聞と東京朝日新聞の題号を朝日新聞に統一
大日本航空が横浜-サイパン-パラオ間定期航空路を開始
勝鬨橋開通
艦上戦闘機にゼロ戦採用
勤労所得の源泉徴収開始
ハティ・マクダニエルがアカデミー賞助演女優賞を受賞

 

きょうのどうぶつ

ここの画像を使用しています。

雨の朝のスズメ。

 

計算終わりました

 

あわせてどうぞ

SOHOのすすめ記事一覧 2019年
お仕事関係の記事のリストです(2019年)。

読みたい論文シリーズ− 2019年3Q
読みたいけと読んでいない論文を、構造式を描きながら紹介します(2019年7〜9月)。

 

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3価化合物の合成。
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昔チオフェノールの生で怒られたことあります。
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描くのが大変なくらいでっかい環状ラクトンを作ります。
1箇所二重結合を入れとくのがいいのでしょうか。
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金属触媒を使うことなくアルデヒドを脱カルボニル化させます
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Cu触媒によるgem-ジボリルアルカンのアミノ化反応
アミノ酸のカルボキシル基がホウ素になったやつ。
Org. Lett. 2019, 21 (12), 4759−4762.

アルキンにボリル基をふたつ導入します
モル比を知りたいところ。
Org. Lett. 2019, 21 (12), 4739−4744.

 

注目のWebコンテンツ

引っ張りに強いカーボンナノチューブの構造を特定 〜軽量で高強度な究極の構造材料の実現に一歩近づく〜
(JST)
https://www.jst.go.jp/pr/annou...

定説覆す発見 10nmサイズの高品質マグネタイト作製で明らかに 〜ナノエレクトロニクスへの展開とマグネタイトの性質の起源解明に期待〜
(JST)
https://www.jst.go.jp/pr/annou...

単独で普通の細胞を直に幹細胞に変えるステミン遺伝子の発見
(名古屋大学)
http://www.nagoya-u.ac.jp/abou...

ヒトが『しっとり感』を感じるメカニズムを解明〜化粧品・自動車・繊維・バーチャルリアリティに応用展開〜
(山形大学)
https://www.yamagata-u.ac.jp/j...

引っ張りに強いカーボンナノチューブの構造を特定 −軽量で高強度な究極の構造材料の実現に一歩近づく−
(京都大学)
http://www.kyoto-u.ac.jp/ja/re...

優しさを伝える介護技術の習熟度をAIで評価する手法を開発 −画像認識で熟練者と初心者の違いを見つける−
(京都大学)
http://www.kyoto-u.ac.jp/ja/re...

 

注目の論文

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[Chem. Lett. 20190710082956, 2019, 8−783]
Enantioselective Aza-Michael/Protonation Reactions in Water
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[Chem. Lett. 20190710082959, 2019, 8−775]
Selective Hydrogen Production from Formate Using Nanoparticle with Homogeneously Polymer-dispersed Platinum Clusters
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[Chem. Lett. 20190710083015, 2019, 8−771]
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ルテニウム  
[Chem. Lett. 20190710083022, 2019, 8−768]
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Tag: Ru, Nu, Ru-catalyzed

パラジウム  
[Chem. Lett. 20190710083035, 2019, 8−760]
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[Chem. Lett. 20190710083034, 2019, 8−764]
Fibronectin Coating on Implant Material Surface Attracted Both Osteoblasts and Bacteria
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[Bull. Chem. Soc. Jpn 20190710083056, 2019, 7−1234]
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[Bull. Chem. Soc. Jpn 20190710083115, 2019, 7−1211]
Two-Way Chromic Systems Based on Tetraarylanthraquinodimethanes: Electrochromism in Solution and Mechanofluorochromism in a Solid State
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[Bull. Chem. Soc. Jpn 20190710083115, 2019, 7−1218]
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[Nature Chemistry 20190710083139, 2019, 7−669]
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[Nature Chemistry 20190710083154, 2019, 7−644]
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[J. Phys. Chem. Lett. 20190710084711, 2019, 13−3710]
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Tag: H, O, O, OV, Ovac, ABS, XAS, e-, P

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[J. Phys. Chem. C 2019071008561, 2019, 26−16281]
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Tag: NS, PE, Au, XPS, Br, PS, STM, Pyr, Py, DFT

[J. Phys. Chem. A 2019071009057, 2019, 26−5633]
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Tag: ISM, R, AIMD, MDS, MD, ABMD, OTS, GS

[J. Phys. Chem. A 20190710090510, 2019, 26−5649]
Time-Dependent Long-Range-Corrected Density-Functional Tight-Binding Method Combined with the Polarizable Continuum Model
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[J. Org. Chem. 20190710090556, 2019, 13−8380]
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Tag: Li, 244-63-3, NH2, DMA, Nu, Me

[J. Org. Chem. 20190710090751, 2019, 13−8552]
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Tag: NR, OS, RE, TS, rds, DMK, DB, ACE, Rh, C, Cat, SiH4

[J. Org. Chem. 20190710090835, 2019, 13−8596]
Topologically Controlled Synthesis of Reversible Macrocyclic Compounds in Microemulsions
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Tag: CM, PD, M

鉄  
[J. Org. Chem. 20190710090839, 2019, 13−8602]
Iron-Promoted Intramolecular Cascade Cyclization for the Synthesis of Selenophene-Fused, Quinoline-Based Heteroacenes
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Tag: AE, Fe, Se, Nu, 91-22-5, DCM, CH2Cl2

[ACS Catal. 20190710091754, 2019, 7−6425]
Pt/TiH2 Catalyst for Ionic Hydrogenation via Stored Hydrides in the Presence of Gaseous H2
(Wu, Qifan; Zhang, Chao; Arai, Masahiko; Zhang, Bin; Shi, Ruhui; Wu, Peixuan; Wang, Zhuangqing; Liu, Qiang; Liu, Ke; Lin, Weiwei; Cheng, Haiyang; Zhao, Fengyu)
Tag: ET, H, Ti, CAL, 104-55-2, e-, C, Cat

CO2還元  
[ACS Catal. 20190710091753, 2019, 7−6305]
Role of a Hydroxide Layer on Cu Electrodes in Electrochemical CO2 Reduction
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Tag: ATR, SEIRAS, GB, Cu, EC, HC, O, CH3CH2OH, ECR, SEIRA, ABS, CPE, CO2R, C2H4, C, CH4, IR, Cat, EtOH

光酸化還元触媒  
[ACS Catal. 20190710092037, 2019, 7−6555]
Keto-Difluoromethylation of Aromatic Alkenes by Photoredox Catalysis: Step-Economical Synthesis of α-CF2H-Substituted Ketones in Flow
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Tag: FP, C, EC, R, LFP, PC, DFT, SES

[ACS Catal. 20190710092120, 2019, 7−6118]
Reductive C–C Coupling by Desulfurizing Gold-Catalyzed Photoreactions
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Tag: St, Au, AA, H, R, UV, ABS, E, El, LE, e-, LED, BL, Alk

[ACS Catal. 2019071009245, 2019, 7−6415]
Deactivation Mechanism of Pd/CeO2–ZrO2 Three-Way Catalysts Analyzed by Chassis-Dynamometer Tests and in Situ Diffuse Reflectance Spectroscopy
(Machida, Masato; Fujiwara, Ayumi; Yoshida, Hiroshi; Ohyama, Junya; Asakura, Hiroyuki; Hosokawa, Saburo; Tanaka, Tsunehiro; Haneda, Masaaki; Tomita, Atsuko; Miki, Takeshi; Iwashina, Katsuya; Endo, Yoshinori; Nakahara, Yunosuke; Minami, Shigekazu; Kato, Naohiro; Hayashi, Yoshiyuki; Goto, Hideki; Hori, Masao; Tsuda, Toyofumi; Miura, Kazuya; Kimata, Fumikazu; Iwachido, Kinichi)
Tag: TR, XR, O, EM, DRS, TWC, ABS, XAS, XRD, e-, C, TPB, GS