(5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester | 255721-46-1

• 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: (5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester
• 英文别名: (+/-)-(Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydropyran-2-yloxy)-cyclopentyl]-5-heptenic acid methyl ester；(Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(2-tetrahydropyranyloxy)cyclopentan-1-yl]-5-heptenoic acid methyl ester；methyl (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• CAS: 255721-46-1
• 化学式: C₁₉H₃₁ClO₅
• 分子量: 374.905
• InChiKey: PGXIXRFMCQTABZ-WFNHWOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以100%的产率得到(5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester
  参考文献：
  名称：

  高选择性 EP2 受体激动剂的合成

  摘要：

  开发了一种合成前列腺素 EP2 受体激动剂 1 的实用方法。该方法包括使用 Sharpless 不对称环氧化程序从烯丙醇 4 制备醛 2 与旋光砜 3 的镁介导的 Julia 烯化。

  DOI：

  10.1055/s-2002-19781
• 作为产物：
  描述：

  (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoic acid 生成 (5Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester
  参考文献：
  名称：

  RADUCHEL, BERND;SKUBALLA, WERNER;VORBRUGGEN, HELMUT

  摘要：

  DOI：

文献信息

• Process for the production of 9beta-chloroprostaglandins
  申请人：Schering Aktiengesellschaft

  公开号：US04806668A1

  公开（公告）日：1989-02-21

  The invention relates to a process for the production of (5-chloro-3-hydroxycyclopentyl) acetaldehydes of formula II ##STR1## in which R signifies a benzyl radical, a tert-butyldimethylsilyl radical or a tert-butyldiphenylsilyl radical, characterized in that a compound of formula I ##STR2## in which R has the meanings already mentioned, is reduced in the presence of a reduction agent.

  该发明涉及一种制备II式（5-氯-3-羟基环戊基）乙醛的方法，其中R表示苄基基团、叔丁基二甲基硅基团或叔丁基二苯基硅基团，其特征在于在还原剂的存在下还原I式化合物，其中I式化合物的公式为：##STR2## 其中R已经提到的含义。
• $g(v)-SUBSTITUTED PHENYL-PROSTAGLANDIN E DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1114816A1

  公开（公告）日：2001-07-11

  An ω-substituted phenyl-prostaglandin derivative of formula (I), a process for the preparation thereof, a medicament comprising it as active ingredient (all symbols have the same meaning as described in the specification). The compounds of the formula (I) bind strongly on PGE2 receptor (especially subtype EP4) and therefore are useful for the prophylaxis and/or treatment of immune diseases (autoimmune diseases (amyotrophic lateral sclerosis (ALS) etc.), post-transplantation graft rejection, etc.), asthma, abnormal bone formation, neurocyte death, pulmopathy, hepatopathy, etc. They are also related to sleeping disorders and platelet coagulations, and therefore they are also applicable to these diseases.

  一种式(I)的ω-取代苯基-前列腺素衍生物，其制备方法，一种以其为活性成分的药物（所有符号的含义与说明书中描述的相同）。 式（I）化合物与 PGE2 受体（尤其是亚型 EP4）结合力强，因此可用于预防和/或治疗免疫性疾病（自身免疫性疾病（肌萎缩性脊髓侧索硬化症（ALS）等）、移植后移植物排斥等）、哮喘、骨形成异常、神经细胞死亡、肺病、肝病等。它们还与睡眠障碍和血小板凝结有关，因此也适用于这些疾病。
• EP1114816
  申请人：——

  公开号：——

  公开（公告）日：——
• A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues
  作者：K Tani

  DOI：10.1016/s0968-0896(02)00008-1

  日期：2002.6

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.
• RADUCHEL, BERND;SKUBALLA, WERNER;VORBRUGGEN, HELMUT
  作者：RADUCHEL, BERND、SKUBALLA, WERNER、VORBRUGGEN, HELMUT

  DOI：——

  日期：——