(2R,3S,4E)-3-methyl-2-phenyl-4-hexen-2-ol | 122489-21-8

• 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: (2R,3S,4E)-3-methyl-2-phenyl-4-hexen-2-ol
• CAS: 122489-21-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: GVYJKVPFHMAXNV-SGHLJCSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4E)-3-methyl-2-phenyl-4-hexen-2-ol 在 sodium hydroxide 、 sodium tetrahydroborate 、 臭氧 作用下， 生成 (2R*,3S*)-2-methyl-3-phenyl-1,3-butanediol
  参考文献：
  名称：

  Hoffmann, Reinhard W.; Sander, Thomas, Chemische Berichte, 1990, vol. 123, # 1, p. 145 - 152

  摘要：

  DOI：
• 作为产物：
  描述：

  (3E)-2-benzyloxy-3-pentene 、 苯乙酮 在 Cp*2Sm(THF)2 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 (2R,3R,4E)-3-methyl-2-phenyl-4-hexen-2-ol 、 (2R,3S,4E)-3-methyl-2-phenyl-4-hexen-2-ol
  参考文献：
  名称：

  Regio- and Stereochemistry on the Electrophilic Trapping of Allylic Samariums Generated by Reductive Cleavage of Allylic Ethers with (C₅Me₅)₂Sm(thf)_n

  摘要：

  The C-O bond of allylic benzyl ethers was selectively cleaved with Cp-2*Sm(thf)(n) to give allylic samarium complexes in good yields. Facility of their bond fission has been found to be comparable to that of the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio- and stereochemistry on the electrophilic trapping of the allylic complexes thus generated remarkably depended on the nature of the electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to yield blanched homoallylic alcohols with anti diasteroselectivity. On the other hand, trapping with silyl chlorides produced linear allylic silanes. Here, a plausible mechanism to account for the difference is proposed.

  DOI：

  10.1021/jo9723016