(1R)-3-exo-mercapto-2-exo-methoxy-1,7,7-trimethylbicyclo<2.2.1>heptane | 158809-10-0

• 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: (1R)-3-exo-mercapto-2-exo-methoxy-1,7,7-trimethylbicyclo<2.2.1>heptane
• 英文别名: (1R,2S,3R)-2-methoxybornane-2-thiol；(1S,2R,3S,4R)-3-methoxy-4,7,7-trimethylbicyclo[2.2.1]heptane-2-thiol
• CAS: 158809-10-0
• 化学式: C₁₁H₂₀OS
• 分子量: 200.345
• InChiKey: XWMOVOCNILLYSX-CDLYGTGVSA-N

物化性质

• 沸点：
  239.2±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 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：

  (1R)-3-exo-mercapto-2-exo-methoxy-1,7,7-trimethylbicyclo<2.2.1>heptane 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (E)-4-benzyloxy-3-[[(Ss,1R,2S,3R)-2-methoxybornane-3-yl]sulfinyl]-2-butenoate
  参考文献：
  名称：

  Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation

  摘要：

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.037
• 作为产物：
  描述：

  bis[(1R,2S,3R)-2-methoxybornane-3-yl]disulfide 在 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以73%的产率得到(1R)-3-exo-mercapto-2-exo-methoxy-1,7,7-trimethylbicyclo<2.2.1>heptane
  参考文献：
  名称：

  Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation

  摘要：

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.037

文献信息

• Synthesis of Enantiomerically Pure Sulfenimines and Sulfinimines Derived from (+)-Camphor
  作者：Yan Li、Wei Zhu、Zhiyong Cheng、Guishu Yang

  DOI：10.1080/00397919908086426

  日期：1999.8.1

  Abstract A series of chiral sulfenimines were synthesized by reaction of thiol derived from (+)-camphor with NCS, liquid NH3 and aldehydes or ketones. Oxidation of the sulfenimines with MCPBA provided enantiomerically pure sulfinimines in excellent yields, compounds which are very useful in the asymmetric synthesis of amine derivatives.

  摘要 通过(+)-樟脑的硫醇与NCS、液态NH3、醛或酮反应合成了一系列手性亚磺亚胺。用 MCPBA 氧化亚磺亚胺以极好的收率提供对映异构纯亚磺亚胺，这些化合物在胺衍生物的不对称合成中非常有用。