3,4-diphenyl-3-buten-2-ol | 131437-38-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-diphenyl-3-buten-2-ol
• 英文别名: 3,4-Diphenyl-buten-3-ol-2-E；(Z)-3,4-diphenylbut-3-en-2-ol；(+/-)-3,4c-diphenyl-but-3-en-2-ol；(z)-3,4-Diphenylbut-3-en-2-ol
• CAS: 131437-38-2
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: HGYJGUOPUPEEKY-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3,4-diphenyl-3-buten-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以84%的产率得到3,4-二苯基丁-3-烯-2-酮
  参考文献：
  名称：

  Addition of Arylboronic Acids to Arylpropargyl Alcohols en Route to Indenes and Quinolines

  摘要：

  A regio- and stereoselective rhodium-catalyzed synthesis of trisubstituted allylic alcohols is described. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.

  DOI：

  10.1021/ol202176g
• 作为产物：
  描述：

  3,4-二苯基丁-3-烯-2-酮 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 3,4-diphenyl-3-buten-2-ol
  参考文献：
  名称：

  Overlap Control of Carbanionoid Reactions. I. Stereoselectivity in Alkaline Epoxidation

  摘要：

  DOI：

  10.1021/ja01510a024

文献信息

• Reactifs de grignard vinyliques γ fonctionnels
  作者：J.G. Duboudin、B. Jousseaume、A Saux

  DOI：10.1016/s0022-328x(00)91989-2

  日期：1979.3

  Primary α-acetylenic alcohols undergo regio- and stereo-specific additiions of Grignard reagents in the presence of cuprous halides. These reactions yield γ-functionally substituted vinylmagnesium compounds. With secondary and tertiary alcohols, the course of the reaction depends on the nature of alcohol and Grignard reagent.

  在卤化亚铜存在下，伯α-炔醇会发生格氏试剂的区域和立体特异性加成。这些反应产生γ-官能取代的乙烯基镁化合物。对于仲和叔醇，反应过程取决于醇和格氏试剂的性质。
• Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes
  作者：Taisuke Itoh、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ol501022d

  日期：2014.5.16

  A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereo-selectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
• Zubritskii, L. M.; Fomina, T. N.; Bal'yan, Kh. V., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 1, p. 63 - 71
  作者：Zubritskii, L. M.、Fomina, T. N.、Bal'yan, Kh. V.

  DOI：——

  日期：——
• Free-Radical-Initiated Coupling Reaction of Alcohols and Alkynes: Not C−O but C−C Bond Formation
  作者：Zhong-Quan Liu、Liang Sun、Jian-Guo Wang、Jie Han、Yan-Kai Zhao、Bo Zhou

  DOI：10.1021/ol900145u

  日期：2009.3.19

  This work demonstrates an efficient method to prepare allylic alcohols via direct C-C bond formation using electron-rich alkynes and aliphatic alcohols initiated by tert-butyl hydroperoxide.
• Exploratory Studies on the Reaction Between Iodoarenes and Acetylenes: One-pot, Pd-[Bmim][BF4] Catalyzed Preparation of Trianisylethylene
  作者：José C. Barros、Andrea L. F. Souza、Joaquim F. M. da Silva、O. A. C. Antunes

  DOI：10.1007/s10562-011-0549-7

  日期：2011.4

  The reaction between iodoarenes and acetylenes mediated by palladium was studied, showing selectivity changes based on the nature of the substituent. A new, phosphine-, copper-, and amine-free methodology was developed, in which the synthesis of trianisylethylene from 4-iodoanisole and trimethylsilylacetylene was promoted presumably by an N-heterocyclic-carbene derived from an ionic liquid and a palladium salt, using ethanol as the hydrogen source.