(Z)-(R)-12-(2-Methoxy-ethoxymethoxy)-octadec-9-enoic acid methyl ester | 404861-00-3

• 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-Methoxy-ethoxymethoxy)-octadec-9-enoic acid methyl ester
• CAS: 404861-00-3
• 化学式: C₂₃H₄₄O₅
• 分子量: 400.599
• InChiKey: BJNBDJFQNPZIFV-QOYCNBSOSA-N

物化性质

• 沸点：
  462.4±40.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  28.0
• 可旋转键数：
  21.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-12-(2-Methoxy-ethoxymethoxy)-octadec-9-enoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以92.99%的产率得到(12R)-12-(2-methoxyethoxymethoxy)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
• 作为产物：
  描述：

  蓖麻油酸 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (Z)-(R)-12-(2-Methoxy-ethoxymethoxy)-octadec-9-enoic acid methyl ester
  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