methyl 2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetate | 1101843-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetate
• 英文别名: methyl 4,5-didehydro-dihydrojasmonate
• CAS: 1101843-11-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: PIVSLSVPWXCWFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetate 在 porcine liver esterase 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 以80%的产率得到2-(4-oxo-5-pentylcyclopent-2-en-1-yl) acetic acid
  参考文献：
  名称：

  New jasmonate analogues as potential anti-inflammatory agents

  摘要：

  In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone ( 1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA(1), PGA(2), and 15-deoxy-Delta(12,14)-PGJ(2)). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that alpha-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.050
• 作为产物：
  描述：

  二氢茉莉酮酸甲酯 在 Pd(DMSO)2(trifluoroacetate)2 作用下， 反应 44.0h， 生成 methyl 2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetate
  参考文献：
  名称：

  CIRCULAR ECONOMY METHODS OF PREPARING UNSATURATED COMPOUNDS

  摘要：

  通过脱氢饱和化合物和/或芳香化合物氢化的方法制备不饱和化合物或类似物已被披露。

  公开号：

  US20170362155A1

文献信息

• CIRCULAR ECONOMY METHODS OF PREPARING UNSATURATED COMPOUNDS
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：US20170362155A1

  公开（公告）日：2017-12-21

  Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

  通过脱氢饱和化合物和/或芳香化合物氢化的方法制备不饱和化合物或类似物已被披露。
• Circular economy methods of preparing unsaturated compounds
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：US10435345B2

  公开（公告）日：2019-10-08

  Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

  本发明公开了通过相应饱和化合物的脱氢反应和/或芳香族化合物的氢化反应制备不饱和化合物或类似物的方法。
• 10.1016/j.mencom.2024.06.019
  作者：Kumar, Sanjay、Koseki, Yoshitaka、Kamishima, Takaaki、Kasai, Hitoshi

  DOI：10.1016/j.mencom.2024.06.019

  日期：——
• New jasmonate analogues as potential anti-inflammatory agents
  作者：Hung The Dang、Hye Ja Lee、Eun Sook Yoo、Jongki Hong、Baoquan Bao、Jae Sue Choi、Jee H. Jung

  DOI：10.1016/j.bmc.2008.10.050

  日期：2008.12.15

  In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone ( 1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA(1), PGA(2), and 15-deoxy-Delta(12,14)-PGJ(2)). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that alpha-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads. (C) 2008 Elsevier Ltd. All rights reserved.