methyl 4,5-didehydrojasmonate | 1103875-23-5

• 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 4,5-didehydrojasmonate
• 英文别名: 4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone；methyl 2-[4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]acetate
• CAS: 1103875-23-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: RRZQRPDFHNQSJD-PLNGDYQASA-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 4,5-didehydrojasmonate 在 porcine liver esterase 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 以80%的产率得到4,5-didehydrojasmonic 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：

  甲基茉莉酸酯 在 三氟乙酸 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以30%的产率得到methyl 4,5-didehydrojasmonate
  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
• 作为试剂：
  描述：

  5-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone 、 对甲苯磺酸 、 碳酸氢钠 在 methyl 4,5-didehydrojasmonate 作用下， 以 苯 为溶剂， 反应 0.33h， 以giving 4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (1-a), R2 =CH3) in a yield of 91%, b.p. 88°-92° C./2.5 mm Hg的产率得到methyl 4,5-didehydrojasmonate
  参考文献：
  名称：

  Process for preparing 2-cyclopentenone derivative and perfume

  摘要：

  一种制备式为##STR1##的2-环戊酮衍生物的方法，其中A为##STR2##，R.sub.2为较低的直链或支链烷基，烯基或芳基烷基，并且含有该衍生物的香水组合物。

  公开号：

  US04237308A1

文献信息

• Partial Syntheses of Methyl Dehydrojasmonate and Tuberolactone
  作者：Paul Dubs、Rita Stüssi

  DOI：10.1002/hlca.19780610308

  日期：1978.4.19

  The natural products methyl dehydrojasmonate (1) and tuberolactone (2) have been synthesized from methyl jasmonate (3) and jasmolactone (4) resp., via sulfenylation-sulfoxide pyrolysis.

  天然产物甲基dehydrojasmonate（1）和tuberolactone（2）从茉莉酮酸甲酯（已被合成3）和jasmolactone（4）RESP。，经由亚磺酰亚砜热解。
• Synthesis and biological activities of methyl 3,7- and 4,5-didehydrojasmonates
  作者：Hiromasa Kiyota、Yasushi Yoneta、Takayuki Oritani

  DOI：10.1016/s0031-9422(97)00374-9

  日期：1997.11

  Methyl 3,7-didehydrojasmonate was synthesized as an analogue of methyl epijasmonate. This analogue inhibited the germination of lettuce seed more strongly than methyl jasmonate. Methyl 4,5-didehydrojasmonate was also synthesized and its biological activities were comparable to those of methyl jasmonate. (C) 1997 Elsevier Science Ltd.
• US4237308A
  申请人：——

  公开号：US4237308A

  公开（公告）日：1980-12-02
• Process for preparing 2-cyclopentenone derivative and perfume
  申请人：Otsuka Kagaku Yakuhin Kabushiki Kaisha

  公开号：US04237308A1

  公开（公告）日：1980-12-02

  A process for preparing 2-cyclopentenone derivative represented by the formula ##STR1## wherein A is ##STR2## and R.sub.2 is lower straight-chain or branched-chain alkyl, alkenyl or aralkyl, and perfume composition containing the derivative.

  一种用于制备由公式##STR1##表示的2-环戊酮衍生物的方法，其中A为##STR2##，R.sub.2为较低的直链或支链烷基、烯烃或芳基烷基，以及含有该衍生物的香水组合物。
• 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.