(1R,2R)-2-(苯基甲硫基)环己烷-1-醇 | 102917-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R)-2-(苯基甲硫基)环己烷-1-醇
• 英文名称: (1R,2R)-2-(benzylthio)cyclohexanol
• 英文别名: (1R,2R)-2-(phenylmethylthio)cyclohexan-1-ol；(1R,2R)-2-benzylsulfanylcyclohexan-1-ol
• CAS: 102917-48-6
• 化学式: C₁₃H₁₈OS
• 分子量: 222.351
• InChiKey: KFEUHCXDITWBNA-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化环己烯 生成 (1R,2R)-2-(苯基甲硫基)环己烷-1-醇
  参考文献：
  名称：

  MUKOYAMA, MITSUAKI;YAMASITA, XIROYUKI

  摘要：

  DOI：

文献信息

• Metal(II)<i>d</i>-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles
  作者：Hiroyuki Yamashita

  DOI：10.1246/bcsj.61.1213

  日期：1988.4

  The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartrates as heterogeneous chiral Lewis acid catalysts. The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartrate, and Zn(II) d-tartrate gave the best enantioselectivity in the respective reactions of 1

  通过使用金属 (II) d-酒石酸盐作为非均相手性路易斯酸催化剂，研究了具有硫醇、苯胺和三甲基甲硅烷基叠氮化物的 meso-2,3-di 取代的环氧乙烷的不对称开环。对映选择性随环氧乙烷、亲核试剂和金属 (II) d-酒石酸盐的组合而变化很大，并且 Zn(II) d-酒石酸盐在 1,2-环氧环己烷与 1-丁硫醇、苯胺、和三甲基甲硅烷基叠氮化物分别以 85%、58% 和 42% ee 提供相应的加合物。此外，研究了由 Zn(II) d-酒石酸盐催化的具有硫醇的外消旋环氧乙烷的动力学拆分。
• Efficient and Enantioselective Kinetic Resolution of Cyclic β-Hydroxy Sulfides by Chiral 1,2-Diamine Catalyzed Asymmetric Acylation
  作者：Yoshiyuki Kawamata、Takeshi Oriyama

  DOI：10.1246/cl.2010.382

  日期：2010.4.5

  Kinetic resolution of cyclic β-hydroxy sulfides has been achieved by reaction with benzoyl chloride in the presence of a catalytic amount (0.1 mol %) of a chiral 1,2-diamine combined with triethylamine. This reaction affords the corresponding benzoates and unreacted alcohols with excellent enantioselectivities.

  通过在手性1,2-二胺（用量为0.1 mol %）和三乙胺的存在下，环状β-羟基硫醇与苯甲酰氯反应，实现了环状β-羟基硫醇的动力学拆分。该反应能够以优异的立体选择性得到相应的苯甲酸盐和未反应的醇。
• ASYMMETRIC RING-OPENING OF CYCLOHEXENE OXIDE WITH VARIOUS THIOLS CATALYZED BY ZINC<i>Lq</i>-TARTRATE
  作者：Hiroyuki Yamashita、Teruaki Mukaiyama

  DOI：10.1246/cl.1985.1643

  日期：1985.11.5

  Optically active trans-2-(arylthio or alkylthio)cyclohexanols are prepared by the asymmetric ring-opening of cyclohexene oxide with various arylthiols or alkylthiols in 52–85% ee by the use of zinc Lq-tartrate as a heterogeneous chiral Lewis acid catalyst.

  旋光性反式-2-（芳硫基或烷硫基）环己醇是通过使用 Lq-酒石酸锌作为非均相手性路易斯酸催化剂，在 52-85% ee 下与各种芳基硫醇或烷硫醇不对称开环氧化环己烯而制备的。
• [EN] PROCESS FOR PREPARING A CONJUGATE LINKING MOIETY<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UNE FRACTION DE LIAISON CONJUGUÉE
  申请人：CYBREXA 2 INC

  公开号：WO2022150596A1

  公开（公告）日：2022-07-14

  The present invention relates to processes for preparing linkers that are useful in the conjugation of therapeutic molecules (e.g., cytotoxic agents) with targeting moieties (e.g., proteins, peptides, antibodies, nanoparticles, nucleic acids). During said processes lipases like lipase B from Candida antarctica were used for enantioselective resolution of (S,S)-2-benzylthiocyclohexanol or (S,S)-2-benzylthiocycloheptanol in presence of acylating agent which are reduced for deprotection to yield (S,S)-2-mercaptocyclohexanol or (S,S)-2-mercaptocyclopentanol which can then be used for linking therapeutic with targeting moieties.

  本发明涉及制备链接剂的过程，该链接剂可用于将治疗分子（例如细胞毒素）与靶向基团（例如蛋白质、肽、抗体、纳米粒子、核酸）结合。在该过程中，利用来自南极酵母的脂肪酶B进行对（S，S）-2-苄基硫代环己醇或（S，S）-2-苄基硫代环庚醇的不对称分离，同时存在酰化剂，然后还原去保护基团，得到（S，S）-2-巯基环己醇或（S，S）-2-巯基环戊醇，这些化合物可用于将治疗分子与靶向基团连接起来。
• Catalytic Asymmetric Ring-Opening Reaction of<i>meso</i>-Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium-Titanium-Salen Complex
  作者：Jiangtao Sun、Minghua Yang、Fang Yuan、Xuefeng Jia、Xia Yang、Yi Pan、Chengjian Zhu

  DOI：10.1002/adsc.200800767

  日期：2009.4

  Abstractmagnified imageA chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso‐epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β‐arylseleno alcohols and β‐hydroxy sulfides were obtained in good yields and high enantioselectivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process.