(±)-1,1-diphenyloct-3-yn-1-ol | 1416327-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-1,1-diphenyloct-3-yn-1-ol
• 英文别名: 1,1-diphenyloct-3-yn-1-ol；1,1-Diphenyloct-3-yn-1-ol
• CAS: 1416327-47-3
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: NGYYDAIRASZHCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (±)-1,1-diphenyloct-3-yn-1-ol 在 dihydrogen hexachloroplatinate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到1,1-diphenyloct-1-en-4-one
  参考文献：
  名称：

  Electrochemically Enabled Carbohydroxylation of Alkenes with H₂O and Organotrifluoroborates

  摘要：

  Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electro-chemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.

  DOI：

  10.1021/jacs.8b08592
• 作为产物：
  描述：

  1-己炔 在 正丁基锂 、 水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (±)-1,1-diphenyloct-3-yn-1-ol
  参考文献：
  名称：

  Electrochemically Enabled Carbohydroxylation of Alkenes with H₂O and Organotrifluoroborates

  摘要：

  Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electro-chemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.

  DOI：

  10.1021/jacs.8b08592

文献信息

• Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic Epoxides
  作者：Aurélien Denichoux、Laurent Debien、Mathieu Cyklinsky、Malika Kaci、Fabrice Chemla、Franck Ferreira、Alejandro Pérez-Luna

  DOI：10.1021/jo302128n

  日期：2013.1.4

  Reaction of dialkylzincs with lithiated acetylenic epoxides is described to give zincates that undergo a 1,2-metallate rearrangement by an anti-SN2′ pathway. This rearrangement occurs with the transfer of an alkyl or a silyl group affording allenylzinc intermediates. Allenic and/or homopropargylic alcohols are obtained upon hydrolysis. Quenching the reaction mixture with aldehydes or ketones is shown

  描述了二烷基锌与锂化的炔属环氧化物的反应以通过反-S N 2'途径产生经历1，2-金属盐重排的锌酸盐。这种重排通过烷基或甲硅烷基的转移发生而得到烯丙基锌中间体。烯丙和/或均丙醇在水解时获得。显示用醛或酮淬灭反应混合物以立体选择性方式获得2-炔基-1,3-二醇。
• Electrochemically Enabled Carbohydroxylation of Alkenes with H₂O and Organotrifluoroborates
  作者：Peng Xiong、Hao Long、Jinshuai Song、Yaohui Wang、Jian-Feng Li、Hai-Chao Xu

  DOI：10.1021/jacs.8b08592

  日期：2018.12.5

  Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electro-chemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.