(+)-methyl 2-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)acetate | 192203-80-8

• 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-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)acetate
• 英文别名: methyl 4,5-dehydrojasmonate；Methyl 4,5-didehydrojasmonate；methyl 2-[(1S,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]acetate
• CAS: 192203-80-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: RRZQRPDFHNQSJD-WQMVXFAESA-N

物化性质

• 沸点：
  314.4±21.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)acetate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 (1S,5R)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-acetic acid
  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：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 aluminum amalgam 、 lithium perchlorate 、 臭氧 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 136.17h， 生成 (+)-methyl 2-((1S,5R)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)acetate
  参考文献：
  名称：

  Enantioselective Synthesis of (-)-Methyl Jasmonate and (+)-Methyl Epijasmonate

  摘要：

  描述了一种高效且灵活的对映选择性合成(-)-甲基茉莉酸酯和(+)-甲基副茉莉酸酯这两种重要植物激素的方法。该步骤利用了一个可以通过磷烯化学从酒石酸方便制备的手性环戊烷基块。

  DOI：

  10.1055/s-1997-3213

文献信息

• In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates
  作者：Hung The Dang、Yoon Mi Lee、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Sun Mee Lee、Sang Kook Lee、Yuna Pyee、Hwa-Jin Chung、Hyung Ryong Moon、Hyung Sik Kim、Jee H. Jung

  DOI：10.1016/j.bmc.2012.04.052

  日期：2012.7

  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.
• Enantioselective Synthesis of (-)-Methyl Jasmonate and (+)-Methyl Epijasmonate
  作者：Gerald Roth、Stephan Kirschbaum、Hans Bestmann

  DOI：10.1055/s-1997-3213

  日期：1997.5

  An efficient and flexible enantioselective synthesis of (-)-methyl jasmonate and (+)-methyl epijasmonate, two important phytohormones, is described. The procedure makes use of a chiral cyclopentanoid building block that can easily be prepared from tartaric acid by phosphorus ylide chemistry.

  描述了一种高效且灵活的对映选择性合成(-)-甲基茉莉酸酯和(+)-甲基副茉莉酸酯这两种重要植物激素的方法。该步骤利用了一个可以通过磷烯化学从酒石酸方便制备的手性环戊烷基块。