(2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-1,5,7-triol | 668470-36-8

• 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: (2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-1,5,7-triol
• 英文别名: (2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyltetradeca-2,12-diene-1,5,7-triol
• CAS: 668470-36-8
• 化学式: C₁₉H₃₆O₄
• 分子量: 328.492
• InChiKey: IEKWMSDUDVJMFU-MOYNMMFTSA-N

物化性质

• 沸点：
  466.2±45.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  23.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-1,5,7-triol 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 以79%的产率得到(2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-7-hydroxy-9-methoxy-8,10-dimethyl-2,12-tetradecadien-5-oidel
  参考文献：
  名称：

  An efficient synthesis of pironetins employing a useful chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one

  摘要：

  A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00556-6
• 作为产物：
  描述：

  (2Z,4R,5R,7S,8S,9R,10S,12E)-1-tert-butyldimethylsilyloxy-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-5,7-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(2Z,4R,5R,7S,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-1,5,7-triol
  参考文献：
  名称：

  An efficient synthesis of pironetins employing a useful chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one

  摘要：

  A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00556-6