(Z,Z)-4-ethyl-4,8-decadien-1-ol | 199926-92-6

• 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,Z)-4-ethyl-4,8-decadien-1-ol
• 英文别名: (4Z,8Z)-4-ethyldeca-4,8-dien-1-ol
• CAS: 199926-92-6
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: KAYHBIABRMFWKE-WHFGVELXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z,Z)-4-ethyl-4,8-decadien-1-ol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z,Z)-4-ethyl-4,8-decadienal
  参考文献：
  名称：

  Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin

  摘要：

  The preparation of an all-Z-triene corresponding to an acyclic premonensin triene is described. In analogy to the Townsend syn-oxidative cyclization hypothesis for natural product biosynthesis, a sequence of regioselective and enantioselective syn-dihydroxylation of the triene, cis-selective syn-oxidative cyclization of the diol-diene, and trans-selective syn-oxidative cyclization of the remaining hydroxyalkene gives the correct stereochemical pattern corresponding to the C and D ring tetrahydrofurans of monensin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01026-0
• 作为产物：
  描述：

  (Z,Z)-4-ethyl-1,4,8-decatriene 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以66%的产率得到(Z,Z)-4-ethyl-4,8-decadien-1-ol
  参考文献：
  名称：

  Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin

  摘要：

  The preparation of an all-Z-triene corresponding to an acyclic premonensin triene is described. In analogy to the Townsend syn-oxidative cyclization hypothesis for natural product biosynthesis, a sequence of regioselective and enantioselective syn-dihydroxylation of the triene, cis-selective syn-oxidative cyclization of the diol-diene, and trans-selective syn-oxidative cyclization of the remaining hydroxyalkene gives the correct stereochemical pattern corresponding to the C and D ring tetrahydrofurans of monensin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01026-0