(Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid

• 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: (Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid
• 英文别名: 15-deoxy-delta12,14-prostaglandin J2；9,10-dihydro-15d-PGJ₂；9,10-dihydro-15-deoxy-Δ12,14-PGJ2；(Z)-7-[(1R,2E)-2-[(E)-oct-2-enylidene]-3-oxocyclopentyl]hept-5-enoic acid
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: AFBJLDUEEOOVHL-GODQJPCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4R,2'Z)-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopenten-1-one 在 吡啶 、 sodium chlorite 、 正丁基锂 、 2-甲基-2-丁烯 、 Stryker's reagent 、 戴斯-马丁氧化剂 、 二异丙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 9.5h， 生成 (Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid
  参考文献：
  名称：

  Total Synthesis of Prostaglandin 15d-PGJ₂ and Investigation of its Effect on the Secretion of IL-6 and IL-12

  摘要：

  An efficient synthesis of 15-deoxy-Delta 12,14-prostaglandin J(2) (15d-PGJ(2), 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated omega-side chain serves in a reinforcing manner.

  DOI：

  10.1021/acs.orglett.5b02181

文献信息

• Total Synthesis of Prostaglandin 15d-PGJ₂ and Investigation of its Effect on the Secretion of IL-6 and IL-12
  作者：Julian Egger、Stefan Fischer、Peter Bretscher、Stefan Freigang、Manfred Kopf、Erick M. Carreira

  DOI：10.1021/acs.orglett.5b02181

  日期：2015.9.4

  An efficient synthesis of 15-deoxy-Delta 12,14-prostaglandin J(2) (15d-PGJ(2), 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated omega-side chain serves in a reinforcing manner.