(3R)-1-phenylthio-4,4-(trimethylene)hexane-3-ol | 255721-57-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3R)-1-phenylthio-4,4-(trimethylene)hexane-3-ol
• 英文别名: (3S)-1-Phenylthio-4,4-propano-3-hexanol；(1S)-1-(1-ethylcyclobutyl)-3-phenylsulfanylpropan-1-ol
• CAS: 255721-57-4
• 化学式: C₁₅H₂₂OS
• 分子量: 250.405
• InChiKey: UZIJJKBHEVSYDB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-1-phenylthio-4,4-(trimethylene)hexane-3-ol 在 palladium on activated charcoal 正丁基锂 、 三甲基氯硅烷 、 Oxone 、 氢气 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 7-{(1R,2R,3R,5R)-5-Chloro-2-[(S)-4-(1-ethyl-cyclobutyl)-4-hydroxy-butyl]-3-hydroxy-cyclopentyl}-heptanoic acid methyl ester
  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
• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-4,4-trimethylene-1-hexanol 在 sodium hydroxide 、 四丁基溴化铵 、 红铝 作用下， 以 甲苯 为溶剂， 生成 (3R)-1-phenylthio-4,4-(trimethylene)hexane-3-ol
  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

文献信息

• &ohgr;-cycloalkyl-prostaglandin E1 derivatives
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06235780B1

  公开（公告）日：2001-05-22

  (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.

  其中R1为OH等；X为Cl，F；R2为H，C1-8烷基，C2-8烯基，C2-8炔基，可能被取代；n为0-4。其非毒性盐或环糊精包合物能够强烈结合EP2亚型受体。因此，它们对于预防和/或治疗免疫性疾病（自身免疫疾病，移植后移植物排斥等），哮喘，异常骨骼形成，神经细胞死亡，肝病，流产，早产或视网膜神经病变（如青光眼）等是有用的。
• 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。
• 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.
• Synthesis of a Highly Selective EP2-Receptor Agonist
  作者：Kousuke Tani、Atsushi Naganawa、Akiharu Ishida、Hiromu Egashira、Yoshihiko Odagaki、Toru Miyazaki、Tomoyuki Hasegawa、Yasufumi Kawanaka、Hisao Nakai、Shuichi Ohuchida、Masaaki Toda

  DOI：10.1055/s-2002-19781

  日期：——

  A practical method for the synthesis of the prostanoid EP2-receptor agonist 1 was developed. This method includes magnesium-mediated Julia olefination of aldehyde 2 with the optically active sulfone 3, which was prepared from allylic alcohol 4 using the Sharpless asymmetric epoxidation procedure.

  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。