(E)-5-phenylmethoxyhex-2-en-1-ol | 671232-61-4

• 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: (E)-5-phenylmethoxyhex-2-en-1-ol
• CAS: 671232-61-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: AGNCHOJVFIOBAJ-AATRIKPKSA-N

物化性质

• 沸点：
  317.6±37.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-5-phenylmethoxyhex-2-en-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以96%的产率得到[(2S,3S)-3-(2-phenylmethoxypropyl)oxiran-2-yl]methanol
  参考文献：
  名称：

  Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

  摘要：

  An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.070
• 作为产物：
  描述：

  3-benzyloxy-1-butanol 在 pyridine-SO3 complex 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 (E)-5-phenylmethoxyhex-2-en-1-ol
  参考文献：
  名称：

  Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

  摘要：

  An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.070