(1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>heptane-2-thiol | 153336-76-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>heptane-2-thiol
• 英文别名: (1R,2S,3R)-2-neopentyloxy-1,7,7-trimethylbicyclo<2.2.1>heptane-3-thiol；(1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo[2.2.1]heptane-2-thiol
• CAS: 153336-76-6
• 化学式: C₁₅H₂₈OS
• 分子量: 256.453
• InChiKey: PCJJFILMJKIBOV-BLTAXRJOSA-N

物化性质

• 沸点：
  302.3±25.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  10.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>heptane-2-thiol 在 N-氯代丁二酰亚胺 、 氨 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.67h， 生成 (NE,R,1S,2R,3S,4R)-N-benzylidene-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo[2.2.1]heptane-2-sulfinamide
  参考文献：
  名称：

  Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

  摘要：

  A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.

  DOI：

  10.1021/jo00083a037
• 作为产物：
  描述：

  在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>heptane-2-thiol
  参考文献：
  名称：

  Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

  摘要：

  A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.

  DOI：

  10.1021/jo00083a037

文献信息

• The study of Lewis acid effect on asymmetric Diels-Alder reactions of new 2-sulfinylbutadienes derived from (1R, 2S, 3R)-3-mercaptocamphan-2-ol
  作者：Teng-Kuei Yang、Han-Yang Chu、Dong-Sheng Lee、Yao-Zhong Jiang、Ta-Shue Chou

  DOI：10.1016/0040-4039(96)00897-0

  日期：1996.6

  The Diels-Alder reactions of N-phenylmaleimide and new chiral 2-sulfinylbutadienes, which were prepared from , produced cycloadducts up to 99% d.e. in the presence of LiClO4 at ambient temperature. On the other hand, we found the facial selectivity of the cycloaddtion changed greatly among various Lewis acids.

  在环境温度下，在LiClO 4存在下，由N-苯基马来酰亚胺和新的手性2-亚磺酰基丁二烯制备的狄尔斯-阿尔德反应可生成高达99％de的环加合物。另一方面，我们发现在各种路易斯酸之间，环加成反应的面部选择性发生了很大变化。
• Influence of chiral thiols on the diastereoselective synthesis of γ-lactams from cyclic anhydrides
  作者：Ashkaan Younai、James C. Fettinger、Jared T. Shaw

  DOI：10.1016/j.tet.2012.03.027

  日期：2012.6

  The synthesis of gamma-lactams from both four-component and imine-anhydride reactions is reported. The synthesis of 2-phenylcyclohexanethiol is described and this compound was evaluated along with an additional seven chiral thiols. A range of selectivity and yields was observed and comparisons to established reactions are made in order to account for the observed reactivity. (c) 2012 Elsevier Ltd. All rights reserved.
• Chiral acetylene thioethers: Synthesis and Pauson-Khand reactions
  作者：Elvira Montenegro、Marta Poch、Albert Moyano、Miquel A Pericàs、Antoni Riera

  DOI：10.1016/s0040-4020(97)00535-8

  日期：1997.6

  Chiral acetylene thioethers have been prepared in excellent yields from the corresponding thiols. The procedure involves the treatment of the corresponding thiolate with 2-bromo-1,1-diethoxyethane followed by double elimination with LDA and, in some cases, alkylation of the acetylide with alkyl or omega-alkenyl iodides. These compounds have been tested in both intra- and intermolecular Pauson-Khand reactions. This study clearly shows that acetylenic thioethers can be excellent substrates for asymmetric versions of this reaction. (C) 1997 Elsevier Science Ltd.
• Efficient synthesis of chiral acetylene dithioethers in enantiomerically pure form
  作者：Jaume Balsells、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/s0957-4166(97)00126-2

  日期：1997.5

  Chiral acetylene dithioethers have been synthesized by the first time in enantiomerically pure form through a high yield (93-100%), one-pot procedure involving the successive treatment of trichloroethylene with three equivalents of lithium bis(trimethylsilyl)amide and two equivalents of a chiral thiol in diethyl ether solution. (C) 1997 Elsevier Science Ltd.
• Asymmetric Diels-Alder reaction of α-sulfinylacrylate derived from (1R, 2S, 3R)-3-mercaptocamphan-2-ol
  作者：Teng-Kuei Yang、Ching-Jung Chen、Dong-Sheng Lee、Ting-Ting Jong、Yao-Zhong Jiang、Ai-Qiao Mi

  DOI：10.1016/0957-4166(95)00420-3

  日期：1996.1

  The Diels-Alder reaction of cyclopentadiene with a new chiral alpha-sulfinylacrylate, which was prepared from MerCO[(1R, 2S, 3R)-3-mercaptocamphan-2-ol] at -78 degrees C in the presence of ZnCl2 produced an endo-cycloadduct with 99.4% d.e. in 84% yield.