(R)-(E)-4-benzyloxy-3-hydroxy-1-phenyl-1-butene | 141939-74-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (R)-(E)-4-benzyloxy-3-hydroxy-1-phenyl-1-butene
• 英文别名: (E,2R)-4-phenyl-1-phenylmethoxybut-3-en-2-ol
• CAS: 141939-74-4
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: XYWDLGMMAUGKPJ-FMQWLBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(E)-4-benzyloxy-3-hydroxy-1-phenyl-1-butene 在 potassium hydride 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 18.0h， 生成 4-benzyloxy-1-trichloroacetamino-1-phenyl-2-butene
  参考文献：
  名称：

  An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction

  摘要：

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.

  DOI：

  10.3987/com-91-s89
• 作为产物：
  描述：

  ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol 在 吡啶 、 chromium(VI) oxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.5h， 生成 (R)-(E)-4-benzyloxy-3-hydroxy-1-phenyl-1-butene
  参考文献：
  名称：

  α，β-环氧甲苯磺酰hydr的烷基化消除

  摘要：

  通过使用烷基镁试剂通过烷基化消除由衍生自手性环氧醛的甲苯磺酰hydr制备光学纯的烯丙醇。

  DOI：

  10.1016/0040-4039(94)02237-6

文献信息

• An Efficient Synthesis of Optically Active 4-Benzyloxy-3-hydoroxy-1-butyne and Its Cross-Coupling Reaction
  作者：Seiichi Takano、Masashi Akiyama、Takumichi Sugihara、Kunio Ogasawara

  DOI：10.3987/com-91-s89

  日期：——

  An efficient procedure for the synthesis of optically active 4-benzyloxy-3-hydroxy-1-butyne (12: R = H) has been established starting with optically active tartrate ester. Cross-coupling reaction of the resulted acetylene (12: R = H) with some aromatic halides (13a approximately h) and transformation of the arylacetylenes (14a approximate h), thus obtained, into the allylic amine derivatives (17a approximate h) have also been examined via the allylic alcohol intermediates (15 a approximately h) by sequential stereoselective reduction and [3,3] sigmatropic rearrangement.
• Alkylative elimination of α,β-epoxy tosylhydrazones
  作者：S. Chandrasekhar、Mohamed Takhi、J.S. Yadav

  DOI：10.1016/0040-4039(94)02237-6

  日期：1995.1

  Optically pure allyl alcohols have been prepared from tosylhydrazones derived from chiral epoxy aldehydes by alkylative elimination utilizing alkyl magnesium reagents.

  通过使用烷基镁试剂通过烷基化消除由衍生自手性环氧醛的甲苯磺酰hydr制备光学纯的烯丙醇。