(5Z,8Z,11Z,14Z)-20-Bromo-16,16-dimethyl-icosa-5,8,11,14-tetraenoyl chloride | 322399-65-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (5Z,8Z,11Z,14Z)-20-Bromo-16,16-dimethyl-icosa-5,8,11,14-tetraenoyl chloride
• CAS: 322399-65-5
• 化学式: C₂₂H₃₄BrClO
• 分子量: 429.868
• InChiKey: MOEJVEVQPDIXMG-YFQJOWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  25.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(氨基甲基)-2-甲氧基苯酚盐酸盐 、 (5Z,8Z,11Z,14Z)-20-Bromo-16,16-dimethyl-icosa-5,8,11,14-tetraenoyl chloride 以 二氯甲烷 为溶剂， 以32%的产率得到O 1861
  参考文献：
  名称：

  The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all-cis)-5,8,11-tetradecatrienoate

  摘要：

  Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00877-2
• 作为产物：
  描述：

  (5Z,8Z,11Z)-14-Iodo-tetradeca-5,8,11-trienoic acid methyl ester 在 lithium hydroxide 、 草酰氯 、 溴 、 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.5h， 生成 (5Z,8Z,11Z,14Z)-20-Bromo-16,16-dimethyl-icosa-5,8,11,14-tetraenoyl chloride
  参考文献：
  名称：

  The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all-cis)-5,8,11-tetradecatrienoate

  摘要：

  Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00877-2