(Z)-4,4-dimethyl-1-phenylpent-1-en-3-ol | 29582-46-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (Z)-4,4-dimethyl-1-phenylpent-1-en-3-ol
• 英文别名: cis-1-t-Butyl-3-phenylallylalkohol；1-Penten-3-ol, 4,4-dimethyl-1-phenyl-, (Z)-
• CAS: 29582-46-5
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: SSLOCCVNUSYUIX-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4,4-dimethyl-1-phenyl-pent-1-yn-3-ol 在 potassium tert-butylate 、 copper(II) acetate monohydrate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 、 叔丁醇 、 四丁基氟化铵 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到(Z)-4,4-dimethyl-1-phenylpent-1-en-3-ol
  参考文献：
  名称：

  Copper-catalyzed Z-selective semihydrogenation of alkynes with hydrosilane: a convenient approach to cis-alkenes

  摘要：

  A copper catalyst generated in situ from widely available copper salt and imidazolium salt in the presence of t-BuOK showed high efficiency for the semihydrogenation of a wide range of internal and terminal alkynes to their corresponding alkenes without obvious over-reduction. Functional groups, such as hydroxyl, nitro, halides, and amino, etc. were tolerated. The Z/E ratios of the obtained alkenes were generally >99%. Finally, semireduction of bulky alkynes also went smoothly. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.053

文献信息

• Mechanism of hydride attack in the reduction of trans-1-tert-butyl-3-phenylallyl and 1-tert-butyl-3-phenylpropargyl alcohols
  作者：Weston T. Borden

  DOI：10.1021/ja00719a024

  日期：1970.8
• Selective C−O Bond Cleavage of Vinyl Ethers with Cp*₂Sm(thf)<i>_n</i> Leading to Vinylsamarium or Enolate Complexes
  作者：Ken Takaki、Masafumi Maruo、Tohru Kamata、Yoshikazu Makioka、Yuzo Fujiwara

  DOI：10.1021/jo961262f

  日期：1996.11.15
• Copper-catalyzed Z-selective semihydrogenation of alkynes with hydrosilane: a convenient approach to cis-alkenes
  作者：Guang-Hui Wang、Huai-Yu Bin、Miao Sun、Shu-Wei Chen、Ji-Hong Liu、Chong-Min Zhong

  DOI：10.1016/j.tet.2014.01.053

  日期：2014.3

  A copper catalyst generated in situ from widely available copper salt and imidazolium salt in the presence of t-BuOK showed high efficiency for the semihydrogenation of a wide range of internal and terminal alkynes to their corresponding alkenes without obvious over-reduction. Functional groups, such as hydroxyl, nitro, halides, and amino, etc. were tolerated. The Z/E ratios of the obtained alkenes were generally >99%. Finally, semireduction of bulky alkynes also went smoothly. (C) 2014 Elsevier Ltd. All rights reserved.