(S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate | 172376-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate
• 英文别名: (S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzenesulfonate)；(S)-3-cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonate；[(3S)-3-cyclohexyl-3-hydroxypropyl] 4-bromobenzenesulfonate
• CAS: 172376-41-9
• 化学式: C₁₅H₂₁BrO₄S
• 分子量: 377.299
• InChiKey: RSKQVELBSOMXHS-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到3-Cyclohexyl-3-oxopropyl 4-bromobenzenesulfonate
  参考文献：
  名称：

  3-Azabicyclo[3.1.0]hexane derivatives useful in therapy

  摘要：

  化合物的结构式（I），其盐及其前药，其中取代基如本文所定义，被披露为在治疗鸦片类物质介导的疾病中有用的鸦片受体结合剂。还描述了制备这类物质的方法。

  公开号：

  US06313312B1
• 作为产物：
  描述：

  1-环己基-1,3-丙二醇 、 4-溴苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate 、
  参考文献：
  名称：

  Synthesis of trans-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonists:  Application of the Cis-Thermal Elimination of Carbonates to Alkaloid Synthesis

  摘要：

  Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3 dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyrodome 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190 degrees C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydrpyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)-piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.

  DOI：

  10.1021/jo951403y

文献信息

• 3-Azabicyclo[3.1.0]hexane derivatives useful in therapy
  申请人：Pfizer INC

  公开号：US06313312B1

  公开（公告）日：2001-11-06

  Compounds of formula (I), their salts and prodrugs thereof, where the substituents are as defined herein are disclosed as opiate binding agents useful in the treatment of opiate-mediated conditions. Also described are processes for making such substances.

  化合物的结构式（I），其盐及其前药，其中取代基如本文所定义，被披露为在治疗鸦片类物质介导的疾病中有用的鸦片受体结合剂。还描述了制备这类物质的方法。
• Treatment of pruritus
  申请人：Pfizer Inc.

  公开号：US05972962A1

  公开（公告）日：1999-10-26

  The use of certain known 1,3,4 trisubstituted 4-aryl-piperidines for the treatment of pruritus in humans and animals is disclosed.

  揭示了利用某些已知的1,3,4-三取代基的4-芳基哌啶类化合物用于治疗人类和动物的瘙痒症状。
• 3-azabicyclo[3.1.0]hexane derivatives useful in therapy
  申请人：Pfizer, Inc.

  公开号：US20030013875A1

  公开（公告）日：2003-01-16

  Compounds of formula (I), their salts and prodrugs thereof, where the substituents are as defined herein are disclosed as opiate binding agents useful in the treatment of opiate-mediated conditions. Also described are processes for making such substances. 1

  公式（I）的化合物、其盐和前药被揭示为鸦片类结合剂，可用于治疗鸦片类介导的疾病，其中取代基的定义如本文所述。还描述了制造这些物质的过程。
• 4-phenylpiperidines for the treatment of pruritic dermatoses
  申请人：Pfizer Inc.

  公开号：US06610711B2

  公开（公告）日：2003-08-26

  Novel compounds having general formula (I), and pharmaceutically and veterinarily acceptable salts thereof wherein R1, R2, R3, W, Y1, Y2, X, n and y are as defined above and processes for their preparation and intermediate compounds prepared therein. The novel compounds are useful for having utility in the treatment of pruritic dermatoses including allergic dermatitis and atopy in animals and humans.

  具有通式（I）及其在药学和兽医学上可接受的盐中，其中R1、R2、R3、W、Y1、Y2、X、n和y如上所定义，并且其制备过程和中间化合物。这些新化合物在治疗动物和人类的瘙痒性皮肤病，包括过敏性皮炎和特应性皮炎方面具有实用性。
• SAR and biological evaluation of novel trans-3,4-dimethyl-4-arylpiperidine derivatives as opioid antagonists
  作者：Nuria Díaz、Mark Benvenga、Paul Emmerson、Ryan Favors、Michael Mangold、Jamie McKinzie、Nita Patel、Steven Peters、Steven Quimby、Harlan Shannon、Miles Siegel、Michael Statnick、Elizabeth Thomas、Joseph Woodland、Peggy Surface、Charles Mitch

  DOI：10.1016/j.bmcl.2005.05.123

  日期：2005.9

  The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. We have developed a SAR study around LY255582 by comparing the effect of the hydroxy group in the 2- and 4-position of the phenyl ring. Also, we have proved that the 3-position of the phenyl ring is optimal for opioid activity. Furthermore, we have successfully replaced the hydroxy group in LY255582 by carbamate and carboxamide groups. The new analogs have high affinity for the opioid receptors comparable to the corresponding phenol. Carboxamide analog 12 has an improved metabolism profile and proved to be efficacious in in vivo studies. (c) 2005 Elsevier Ltd. All rights reserved.