(Z)-(R)-12-(2,2,2-Trichloro-ethoxycarbonyloxy)-octadec-9-enoic acid | 258349-75-6

• 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)-(R)-12-(2,2,2-Trichloro-ethoxycarbonyloxy)-octadec-9-enoic acid
• CAS: 258349-75-6
• 化学式: C₂₁H₃₅Cl₃O₅
• 分子量: 473.865
• InChiKey: MVYKVURTDSBEGU-ZVBPTUHVSA-N

物化性质

• 沸点：
  519.6±50.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-12-(2,2,2-Trichloro-ethoxycarbonyloxy)-octadec-9-enoic acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of phosphatidylcholines containing ricinoleic acid

  摘要：

  1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only beta -methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphochofine), respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01057-2
• 作为产物：
  描述：

  蓖麻油酸 在 吡啶 、 盐酸 、 lipase PS from Pseudomonas cepacea 作用下， 以 phosphate buffer 、 乙醚 为溶剂， 反应 24.5h， 生成 (Z)-(R)-12-(2,2,2-Trichloro-ethoxycarbonyloxy)-octadec-9-enoic acid
  参考文献：
  名称：

  Synthesis of phosphatidylcholines containing ricinoleic acid

  摘要：

  1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only beta -methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphochofine), respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01057-2