4-{[4-(1-hydroxy-1-phenyl)ethyl]phenyl}-2-phenyl-2-butanol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-{[4-(1-hydroxy-1-phenyl)ethyl]phenyl}-2-phenyl-2-butanol
• 英文别名: 4-[4-(1-Hydroxy-1-phenylethyl)phenyl]-2-phenylbutan-2-ol；4-[4-(1-hydroxy-1-phenylethyl)phenyl]-2-phenylbutan-2-ol
• 化学式: C₂₄H₂₆O₂
• 分子量: 346.469
• InChiKey: XUCXHDBCHWGEHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙醇 在 萘 、 lithium 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 29.0h， 生成 4-{[4-(1-hydroxy-1-phenyl)ethyl]phenyl}-2-phenyl-2-butanol
  参考文献：
  名称：

  Lithiophenylalkyllithiums: new dilithium reagents having both sp2- and sp3-hybridised remote carbanionic centres

  摘要：

  The reaction of chloro-(2-chloroethyl)benzenes (1), 4-chloro-(3-chloropropyl)benzene (3) or 4-chlorophenyl chloromethyl ether (5) with lithium power using naphthalene as the electron shuttle (8 mol%) in the presence of different carbonyl compounds [Bu'CHO, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, PhCOMe] in THF at -78 to 20 degreesC gives, after hydrolysis with water, the expected diols 2, 4 or 6, respectively. Bromo-2-(chloroethyl)benzenes (7) are treated with n-BuLi in THF at -100 degreesC, so the corresponding bromine-lithium exchanges takes place giving an intermediate, which is trapped by treatment with benzaldehyde or cyclohexanone, affording intermediates 9, which are submitted to a naphthalene-catalysed (8 mol%) lithiation with lithium power as above, followed by reaction with 3-pentanone and final hydrolysis with water, to give differently substituted diols 10. Some diols 2 are transformed into either the corresponding oxepane 11 or dienes 12 under Mitsunobu type conditions or by acidic treatment, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01473-0

文献信息

• Lithiophenylalkyllithiums: new dilithium reagents having both sp2- and sp3-hybridised remote carbanionic centres
  作者：Miguel Yus、Diego J Ramón、Inmaculada Gómez

  DOI：10.1016/s0022-328x(02)01473-0

  日期：2002.12

  The reaction of chloro-(2-chloroethyl)benzenes (1), 4-chloro-(3-chloropropyl)benzene (3) or 4-chlorophenyl chloromethyl ether (5) with lithium power using naphthalene as the electron shuttle (8 mol%) in the presence of different carbonyl compounds [Bu'CHO, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, PhCOMe] in THF at -78 to 20 degreesC gives, after hydrolysis with water, the expected diols 2, 4 or 6, respectively. Bromo-2-(chloroethyl)benzenes (7) are treated with n-BuLi in THF at -100 degreesC, so the corresponding bromine-lithium exchanges takes place giving an intermediate, which is trapped by treatment with benzaldehyde or cyclohexanone, affording intermediates 9, which are submitted to a naphthalene-catalysed (8 mol%) lithiation with lithium power as above, followed by reaction with 3-pentanone and final hydrolysis with water, to give differently substituted diols 10. Some diols 2 are transformed into either the corresponding oxepane 11 or dienes 12 under Mitsunobu type conditions or by acidic treatment, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.