(1R,2S,3R,4S)-3-((R)-3,3-Dimethyl-but-1-yne-1-sulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol | 502917-83-1

• 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,2S,3R,4S)-3-((R)-3,3-Dimethyl-but-1-yne-1-sulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol
• CAS: 502917-83-1
• 化学式: C₁₆H₂₆O₂S
• 分子量: 282.447
• InChiKey: WCRNACTZADJWHF-JMMPCOCHSA-N

物化性质

• 沸点：
  399.0±44.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-3-((R)-3,3-Dimethyl-but-1-yne-1-sulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 水 、 diethylzinc 、 sodium hydride 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 110.17h， 生成 4-[(Ss)-[(1R,2S,3R)-2-methoxybornane-3-yl]sulfinyl]-5H-furan-2-one
  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：

  (1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol 在 六甲基磷酰三胺 、 正丁基锂 、 sodium iodate 、 间氯过氧苯甲酸 、 氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 (1R,2S,3R,4S)-3-((R)-3,3-Dimethyl-but-1-yne-1-sulfinyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol
  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

• Maezaki, Naoyoshi; Yagi, Suguru; Ohsawa, Shizuka, Tetrahedron Asymmetry, 2002, vol. 13, # 18, p. 1960 - 1964
  作者：Maezaki, Naoyoshi、Yagi, Suguru、Ohsawa, Shizuka、Ohishi, Hirofumi、Tanaka, Tetsuaki

  DOI：——

  日期：——