Benzoic acid (2Z,5Z,8Z,11Z)-(R)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester | 634179-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (2Z,5Z,8Z,11Z)-(R)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester
• 英文别名: [(5R,6Z,9Z,12Z,15Z)-20-methoxy-20-oxoicosa-6,9,12,15-tetraen-5-yl] benzoate
• CAS: 634179-27-4
• 化学式: C₂₈H₃₈O₄
• 分子量: 438.607
• InChiKey: NRCJXXQBEYLADJ-KOHUDKHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2Z,5Z,8Z,11Z)-(R)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester 在 甲醇 、 sodium methylate 作用下， 反应 8.0h， 以90%的产率得到methyl (16R,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoate
  参考文献：
  名称：

  Practical, asymmetric synthesis of 16-hydroxyeicosa-5( Z ),8( Z ), 11( Z ),14( Z )-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity

  摘要：

  An asymmetric synthesis of 16-HETE, an endogenous inhibitor of neutrophil activity, was achieved in six steps from R-(-)-glycidyl benzyl ether in 28% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.005
• 作为产物：
  描述：

  [(2R)-1-phenylmethoxyhexan-2-yl] benzoate 在 palladium on activated charcoal 六甲基磷酰三胺 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~23.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 Benzoic acid (2Z,5Z,8Z,11Z)-(R)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester
  参考文献：
  名称：

  Practical, asymmetric synthesis of 16-hydroxyeicosa-5( Z ),8( Z ), 11( Z ),14( Z )-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity

  摘要：

  An asymmetric synthesis of 16-HETE, an endogenous inhibitor of neutrophil activity, was achieved in six steps from R-(-)-glycidyl benzyl ether in 28% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.005

文献信息

• Practical, asymmetric synthesis of 16-hydroxyeicosa-5( Z ),8( Z ), 11( Z ),14( Z )-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity
  作者：Y.Krishna Reddy、L.Manmohan Reddy、Jorge H Capdevila、J.R Falck

  DOI：10.1016/j.bmcl.2003.08.005

  日期：2003.11

  An asymmetric synthesis of 16-HETE, an endogenous inhibitor of neutrophil activity, was achieved in six steps from R-(-)-glycidyl benzyl ether in 28% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.