4,4-trimethylene-2-hexen-1-ol | 255721-51-8

• 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: 4,4-trimethylene-2-hexen-1-ol
• 英文别名: 4,4-(trimethylene)-2-hexenol；(E)-3-(1-ethylcyclobutyl)prop-2-en-1-ol
• CAS: 255721-51-8
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: XDHZMHOVEYQNHB-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-trimethylene-2-hexen-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-2,3-epoxy-4,4-trimethylene-1-hexanol
  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：

  1-ethylcyclobutanecarbaldehyde 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 4,4-trimethylene-2-hexen-1-ol
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(02)00008-1

文献信息

• 9-Chloro-15-deoxyprostaglandin derivatives, process for their preparation and their use as medicaments
  申请人：Buchmann Bernd

  公开号：US20070203096A1

  公开（公告）日：2007-08-30

  The present invention relates to 9-chloroprostaglandin derivatives of the general formula I which may be advantageous for the treatment of fertility problems.

  本发明涉及一般式I的9-氯前列腺素衍生物，可能对治疗生育问题有益。
• Omega-cycloalkyl-prostaglandin E1 derivatives
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0974580A1

  公开（公告）日：2000-01-26

  ω-Cycloalkyl-prostaglandin E1 derivatives of formula (I) wherein R1 is OH etc.; X is Cl, F; R2 is H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl which may be substituted; n is 0-4.), non-toxic salts thereof or cyclodextrin clathrates thereof can strongly bind on EP2 subtype receptor. Therefore, they are useful for the prevention and/or treatment of immunological diseases (autoimmune diseases, post-transplantation graft rejection etc.), asthma, abnormal bone formation, neuronal cell death, hepatopathy, abortion, premature birth or retina neuropathy (e.g. glaucoma) etc.

  式(I)的ω-环烷基-前列腺素 E1 衍生物 其中 R1 是 OH 等；X 是 Cl、F；R2 是 H、C1-8 烷基、C2-8 烯基、C2-8 炔基，可被取代；n 是 0-4）、其无毒盐或其环糊精凝胶能与 EP2 亚型受体强结合。因此，它们可用于预防和/或治疗免疫性疾病（自身免疫性疾病、移植后移植物排斥反应等）、哮喘、骨骼形成异常、神经细胞死亡、肝病、流产、早产或视网膜神经病变（如青光眼）等。
• WO2007/57232
  申请人：——

  公开号：——

  公开（公告）日：——
• US6235780B1
  申请人：——

  公开号：US6235780B1

  公开（公告）日：2001-05-22
• 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.