trans-2-(p-tolylthio)cyclopentanol | 87184-65-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: trans-2-(p-tolylthio)cyclopentanol
• 英文别名: (+/-)-trans-2-p-tolylsulfanyl-cyclopentanol；(+/-)-trans-2-p-Tolylmercapto-cyclopentanol；trans-2-p-Tolyl-mercapto-1-hydroxy-cyclopentan；(1S,2S)-2-(4-methylphenyl)sulfanylcyclopentan-1-ol
• CAS: 87184-65-4
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: NECGTYVPUVRWNL-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  trans-2-(p-tolylthio)cyclopentanol 在 吡啶 、 过氧化氢苯甲酰 、 对甲苯磺酰氯 作用下， 反应 3.0h， 生成 trans-2-p-Tolylsulfonyl-1-chlorcyclopentan
  参考文献：
  名称：

  The Stereochemistry of the Nucleophilic Addition of p-Toluenethiol to 1-p-Tolylsulfonylcyclopentene¹

  摘要：

  DOI：

  10.1021/jo01038a018
• 作为产物：
  描述：

  1,2-环氧环戊烷 、 4-甲苯硫酚 在 sodium hydroxide 作用下， 生成 trans-2-(p-tolylthio)cyclopentanol
  参考文献：
  名称：

  Elimination Reactions in Cyclic Systems. I. cis Eliminations in the Cyclohexane and Cyclopentane Series¹

  摘要：

  DOI：

  10.1021/ja01610a017

文献信息

• Stereocontrolled Reduction of 2-(<i>p</i>-Tolylsulfinyl)cycloalkanones under Basic Conditions: π-Facial Selection in Cyclic Systems Directed by a Chiral Side Chain
  作者：Katsuyuki Ogura、Michio Ishida、Makoto Fujita

  DOI：10.1246/bcsj.62.3987

  日期：1989.12

  Reduction of a 2-(p-tolylsulfinyl)cycloalkanone with sodium borohydride in methanol–triethylamine is accompanied by rapid epimerization at C2. Under the conditions employed here, the π-facial selectivity of the reduction is directed by the side chain chirality and, among four possible isomers of the corresponding cycloalkanol, one isomer is given with high selectivities up to 85%.

  用硼氢化钠在甲醇-三乙胺中还原2-(p-甲苯硫酰基)环烷酮时，C2处会迅速发生表异构化。在这里采用的条件下，减肥的π面选择性受侧链手性影响，在相应的环烷醇的四种可能异构体中，有一种异构体的选择性高达85%。
• Salan-Vanadium Catalyzed Enantioselective Desymmetrization of meso-Epoxides with Aromatic Thiols
  作者：Jiangtao Sun、Weijin Gu、Yijun Huang、Xu Pan、Chengjian Zhu

  DOI：10.2174/157017809788489990

  日期：2009.6.1

  The first example of salan-vanadium catalyzed enantioselective ring-opening of meso-epoxides has been reported, which furnished β-hydroxy sulfides in good yields and moderate enantioselectivities.

  首次报道了以salan-钒为催化剂的手性选择性开环反应，该反应能够高效地生成β-羟基硫化物，并具有适度的对映选择性。
• Convenient preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium into chalcogen-chalcogen bonds. Application in the ring-opening of epoxides
  作者：Jennifer Dowsland、Fiona McKerlie、David J Procter

  DOI：10.1016/s0040-4039(00)00687-0

  日期：2000.6

  Convenient conditions are reported for the preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium metal into the chalcogen–chalcogen bond of disulfides, diselenides, and ditellurides. The resulting complexes have been found to transfer arylsulfanyl, -selenanyl, and -telluranyl groups to epoxides in a facile ring-opening reaction. The ytterbium(III) chalcogenolate complexes

  据报道，通过将metal金属插入二硫化物，二硒化物和二碲化物的硫属元素-硫属元素键中，可以方便地制备cha（III）硫属元素化物配合物。已经发现，在容易的开环反应中，所得的络合物将芳基硫烷基，-亚硒基和-四氢呋喃基转移到环氧化物上。Lewis硫氰酸）（III）络合物由于其路易斯酸性性质，似乎在活化环氧化物中起双重作用，并向配位的底物提供亲核试剂。
• Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by heterobimetallic Ti–Ga–Salen system
  作者：Jiangtao Sun、Fang Yuan、Minghua Yang、Yi Pan、Chengjian Zhu

  DOI：10.1016/j.tetlet.2008.11.060

  日期：2009.2

  The enantioselective ring-opening reaction of meso-epoxides with aryl thiols catalyzed by a chiral heterobimetallic Ti–Ga–Salen complex was realized, and the 1,2-mercapto alcohols were obtained in good yields and moderate to high enantioselectivities (up to 92% ee). A strong synergistic cooperation between different Lewis acids in the system was exhibited in the catalytic process.

  的对映选择性开环反应的内消旋环氧化物与芳基硫醇催化由手性异核的Ti-Ga的Salen配复合物实现，该1,2-二巯基醇以良好产率获得和中到高对映选择性（高达92％ ee）。在催化过程中，体系中的不同路易斯酸之间表现出强烈的协同作用。
• 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.