[読みたい論文] α,β-不飽和ケトンの定電流電解

Viewed: 19:37:48 in December 11, 2019

Posted: June 13, 2019

Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources (Huang, Binbin; Li, Yanan; Yang, Chao; Xia, Wujiong)
Chem. Commun. 2019, 55 (47), 6731−6734.

Keywords: CCE; Pt; ammonium chloride; MeOH; DMSO


α,β-不飽和ケトンの定電流電解(constant current electrolysis, CCE)について報告しているようです。両極共に白金ですね。

Supporting informationで基質の適用範囲をみたのですが、β炭素にはアリール基が結合していることが必須っぽい印象でした。一方、カルボニル基に直接結合する方はアリール基でもアルキル基でも大丈夫のようです。

反応自体はシンプルなのですが気になる点が。反応機構を調べる検討の中で重水素化したメタノールを使った例がいくつかあるのですが、その中に、下のような重水素化率の表示がありました。118% Dというのは、そこの炭素原子に結合ている2つの水素原子の両方が「重たい奴」ということなのでしょうか。だとすると、ここの位置でのH/D交換が起こっていることになるわけで。論文の本筋ではないことかもしれませんが。


この他にも塩化アンモニウムの役割がはっきりしないので、読みたい論文に追加です。そもそも何のために添加しているのでしょうね。

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。

 

1999年はこんな年

人名反応など
Fukuyamaインドール合成(第2世代) [Doi 1]
ノーベル化学賞
フェムト秒分光学を用いた化学反応の遷移状態の研究
(Ahmed Hassan Zewail)
できごと
Org. Lett.創刊
ユーロが銀行間取り引きなどの通貨として導入される
大阪06市内局番4桁化
「バイアグラ」が厚生省により認可される
地域振興券の発行が日本全国で始まる
iモードサービスがスタート
「だんご3兄弟」(速水けんたろう・茂森あゆみ)
能登半島沖不審船事件
ゼロ金利政策実施
医薬品の一部が医薬部外品となる
「GOLDFINGER '99」(郷ひろみ)
「鉄道員(ぽっぽや)」公開
「キョロちゃん」放送開始(テレビ東京)
瀬戸内しまなみ海道が開通
ナンバープレートの分類番号3桁化と希望番号制
「AIBO」の発売(ソニー)
NTT分割(NTT東日本・NTT西日本・NTTコミュニケーションズ)
ダイオキシン類対策特別措置法制定
ユニクロブーム
「アポロ」(ポルノグラフィティ)
東海村JCO臨界事故
「ONE PIECE」放送開始(フジテレビ)
「Love, Day After Tomorrow」倉木麻衣
国会で初の党首討論
世界で一番悲しいVゴール

 

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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2Q
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4〜6月)。

 

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手抜きですすんません。
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水素の行方は?
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[読みたい論文] 試されるイオン液体
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[読みたい論文] インドールからBN-ナフタレンを作る
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Org. Lett. 2019, 21 (10), 3855−3860.

[読みたい論文] 借りてきたアシルアルミニウム
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注目のWebコンテンツ

体内リズムの発現に必要なDNAのスイッチを発見 −蛋白質をコードしないノンコーディング領域のDNA配列が活躍−
(京都大学)
http://www.kyoto-u.ac.jp/ja/re...

B型肝炎ウイルス抑制物質の作用機序解明 −新規抗B型肝炎治療薬の開発へ期待−
(京都大学)
http://www.kyoto-u.ac.jp/ja/re...

ワイル粒子がつなぐ量子化された伝導を観測
(科学技術振興機)
https://www.jst.go.jp/pr/annou...

新規色素設計指針を開発 −世界最高の太陽光エネルギー変換効率の実現に向けて−
(京都大学)
http://www.kyoto-u.ac.jp/ja/re...

中温域で世界最高の伝導度を示すヒドリドイオン伝導体を実現 燃料電池や電解水素化反応の効率化などに貢献
(東京工業大学)
https://www.titech.ac.jp/news/...

TYK2遺伝子のレアバリアントが関節リウマチ発症を抑制 −特定のタンパク質ドメインを標的とした治療法の開発へ−
(理化学研究所)
http://www.riken.jp/pr/press/2...

水を推進剤とした超小型衛星用エンジン及び実証衛星の開発に成功 〜 世界初「国際宇宙ステーションからの水推進エンジンを搭載した超小型衛星の宇宙への放出」の実現へ 〜
(東京大学)
https://www.t.u-tokyo.ac.jp/fo...

津波を記録していたムール貝 〜貝がらの元素分析から明らかになった津波による沿岸環境の変化〜
(東京大学)
https://www.aori.u-tokyo.ac.jp...

地熱発電の調査・評価手法の最適化などに関する技術開発に着手 ―環境アセスメントの円滑化による地熱発電の導入拡大を目指す―
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https://www.nedo.go.jp/news/pr...

 

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Tag: DG, Cu, OAP, PhOH

パラジウム  
[ACS Catal. 20190612021117, 2019, 6−5383]
Enhanced Activity of Heterogeneous Pd(II) Catalysts on Acid-Functionalized Metal–Organic Frameworks
(Otake, Ken-ichi; Ye, Jingyun; Mandal, Mukunda; Islamoglu, Timur; Buru, Cassandra T.; Hupp, Joseph T.; Delferro, Massimiliano; Truhlar, Donald G.; Cramer, Christopher J.; Farha, Omar K.)
Tag: PE, Hf, Pd, ES, QM, XPS, PS, FG, e-, C, VS, DFT, Cat

ナノ粒子  
[ACS Catal. 20190612021231, 2019, 6−5574]
Interfacial Control of Catalytic Activity in the Aldol Condensation: Combining the Effects of Hydrophobic Environments and Water
(Singappuli-Arachchige, Dilini; Kobayashi, Takeshi; Wang, Zhuoran; Burkhow, Sadie J.; Smith, Emily A.; Pruski, Marek; Slowing, Igor I.)
Tag: ah, MS, MSN, Hex, NH2, MSNP, NP, SNP, SB, e-, C, Cat

[ACS Catal. 20190612021352, 2019, 6−5742]
Photocatalytic Activation of C–H Bonds by Spatially Controlled Chlorine and Titanium on the Silicate Layer
(Tsunoji, Nao; Nishida, Hidechika; Ide, Yusuke; Komaguchi, Kenji; Hayakawa, Shinjiro; Yagenji, Yuya; Sadakane, Masahiro; Sano, Tsuneji)
Tag: acac, ET, R, Ti, O, Cl, CHX, cy-hex, CyOH, 108-94-1, e-, C, Cat, CyH

[Chem. Eur. J. 20190612021549, 2019, 32−7759]
Selective Formation of a Mixed-Valence State from Linearly Bridged Oligo(aromatic diamines): Drastic Structural Change into a Folded Columnar Stack for Half-filled Polycations
(Nojo, Wataru; Ishigaki, Yusuke; Takeda, Takashi; Akutagawa, Tomoyuki; Suzuki, Takanori)
Tag: MV, ES, e-

[Chem. Eur. J. 20190612021633, 2019, 32−7711]
Proton Transfer Accompanied by the Oxidation of Adenosine
(Choi, Jungkweon; Tojo, Sachiko; Ahn, Doo-Sik; Fujitsuka, Mamoru; Miyamoto, Shunichi; Kobayashi, Kazuo; Ihee, Hyotcherl; Majima, Tetsuro)
Tag: PT, RR, ADO, pmd, TR, R, IMD, imH, Him, imid, TA, ABS, M

[Chem. Eur. J. 2019061202170, 2019, 32−7679]
Optimization of Aqueous Stability versus Ï?-Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live-Cell Fluorescence Imaging
(Griesbeck, Stefanie; Ferger, Matthias; Czernetzi, Corinna; Wang, Chenguang; Bertermann, RÃdiger; Friedrich, Alexandra; Haehnel, Martin; Sieh, Daniel; Taki, Masayasu; Yamaguchi, Shigehiro; Marder, Todd B.)
Tag: FL, QY, anth, ANT, AN, TAB

[Chem. Eur. J. 2019061202175, 2019, 32−7669]
Robust Triplatinum Redox-Chromophore for a Post-Synthetic Color-Tunable Electrochromic System
(Yoshida, Masaki; Shitama, Hotaka; Sameera, W. M. C.; Kobayashi, Atsushi; Kato, Masako)
Tag: ECD, EC, ET, e-

[Chem. Eur. J. 2019061202178, 2019, 32−7649]
Ï??Ï? Stacking Interaction in an Oxidized CuII–Salen Complex with a Side-Chain Indole Ring: An Approach to the Function of the Tryptophan in the Active Site of Galactose Oxidase
(Oshita, Hiromi; Suzuki, Takashi; Kawashima, Kyohei; Abe, Hitoshi; Tani, Fumito; Mori, Seiji; Yajima, Tatsuo; Shimazaki, Yuichi)
Tag: GAO, R, IND, Trp, W, Gal, ABS, GO, SC, e-

[Chem. Eur. J. 20190612021750, 2019, 32−7618]
Synthesis of meso-Alkyl-Substituted Norcorrole–NiII Complexes and Conversion to 5-Oxaporphyrins(2.0.1.0)
(Liu, Si-Yu; Tanaka, Hiroko; Nozawa, Ryo; Fukui, Norihito; Shinokubo, Hiroshi)
Tag: cHex, Cy, cHx, CyHx, H, tBu, t-Bu, Na, Bu, iPr, i-Pr, Na2CO3, HP, H2O2, Alk