(Z)-(2R,5S)-6-Benzyloxy-2,4-dimethyl-hex-3-ene-1,5-diol | 115857-48-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-(2R,5S)-6-Benzyloxy-2,4-dimethyl-hex-3-ene-1,5-diol
• 英文别名: (Z,2R,5S)-2,4-dimethyl-6-phenylmethoxyhex-3-ene-1,5-diol
• CAS: 115857-48-2
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: JOQHODAITRUZSO-LJIOFZCZSA-N

物化性质

• 沸点：
  411.9±45.0 °C(predicted)
• 密度：
  1.072±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (E)-(4S,5R)-6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenol 生成 (Z)-(2R,5S)-6-Benzyloxy-2,4-dimethyl-hex-3-ene-1,5-diol
  参考文献：
  名称：

  MARSHALL, JAMES A.;TROMETER, JOSEPH D.;BLOUGH, BRUCE E.;CRUTE, THOMAS, J. ORG. CHEM., 53,(1988) N 18, C. 4274-4282

  摘要：

  DOI：

文献信息

• Stereochemistry of SN2' additions to acyclic vinyloxiranes
  作者：James A. Marshall、Joseph D. Trometer、Bruce E. Blough、Thomas D. Crute

  DOI：10.1021/jo00253a020

  日期：1988.9
• Diastereodifferentiation in SN2' additions of methylcuprates to nonracemic acyclic vinyloxiranes
  作者：James A. Marshall、Bruce E. Blough

  DOI：10.1021/jo00006a049

  日期：1991.3

  S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).