isopropyl jasmonate | 909404-60-0

• 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: isopropyl jasmonate
• CAS: 909404-60-0
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: VILBCNUPFMPEHA-NTQVKLLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  isopropyl jasmonate 在 磷酸烯丙基二乙酯 、 palladium diacetate 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 isopropyl 4,5-dehydrojasmonate
  参考文献：
  名称：

  In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

  摘要：

  A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.052
• 作为产物：
  描述：

  2-((1R,2R)-3-oxo-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetyl chloride 、 异丙醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 isopropyl jasmonate
  参考文献：
  名称：

  In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

  摘要：

  A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.052