6-endo-(methylthio)bicyclo[2.2.1]heptan-2-one | 139689-76-2

• 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: 6-endo-(methylthio)bicyclo[2.2.1]heptan-2-one
• 英文别名: (1R,4S,6R)-6-methylsulfanylbicyclo[2.2.1]heptan-2-one
• CAS: 139689-76-2
• 化学式: C₈H₁₂OS
• 分子量: 156.249
• InChiKey: ZYHGCLVKNVLFPB-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-endo-(methylthio)bicyclo[2.2.1]heptan-2-one 在 3 A molecular sieve 、 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 Benzyl-((1S,2R,4R,6S)-6-methylsulfanyl-bicyclo[2.2.1]hept-2-yl)-amine
  参考文献：
  名称：

  A new synthesis of 2-substituted 6-endo-(methylthio)bicyclo[2.2.1]heptanes. Synthesis and crystal and molecular structure of a conformationally restricted methionine analog

  摘要：

  A new and advantageous synthesis of 2-endo-substituted-6-endo-(methylthio)bicyclo[2.2.1]heptanes, especially suitable for the preparation of such compounds with 2-endo-hydroxy and amino substituents, is presented. Also reported is the synthesis of the conformationally restricted methionine analogue (+/-)-2-endo-amino-6-endo-(methylthio)bicyclo[2.2.1]heptane-2-exo-carboxylic acid and its crystal and molecular structure determined by X-ray crystallographic techniques.

  DOI：

  10.1021/jo00035a026
• 作为产物：
  描述：

  tert-Butyl-((1S,2S,4R,6S)-6-methanesulfonyl-bicyclo[2.2.1]hept-2-yloxy)-dimethyl-silane 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 72.25h， 生成 6-endo-(methylthio)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  A new synthesis of 2-substituted 6-endo-(methylthio)bicyclo[2.2.1]heptanes. Synthesis and crystal and molecular structure of a conformationally restricted methionine analog

  摘要：

  A new and advantageous synthesis of 2-endo-substituted-6-endo-(methylthio)bicyclo[2.2.1]heptanes, especially suitable for the preparation of such compounds with 2-endo-hydroxy and amino substituents, is presented. Also reported is the synthesis of the conformationally restricted methionine analogue (+/-)-2-endo-amino-6-endo-(methylthio)bicyclo[2.2.1]heptane-2-exo-carboxylic acid and its crystal and molecular structure determined by X-ray crystallographic techniques.

  DOI：

  10.1021/jo00035a026

文献信息

• Interactions of Arenes and Thioethers Resulting in Facilitated Oxidation
  作者：Woo Jin Chung、Malika Ammam、Nadine E. Gruhn、Gary S. Nichol、Waheguru P. Singh、George S. Wilson、Richard S. Glass

  DOI：10.1021/ol802683s

  日期：2009.1.15

  Synthesis of 6-endo and 6-exomethylthio-2-endoarylbicyclo[2.2.1]heptanes was accomplished stereoselectively. The ionization energies, determined by photoelectron spectroscopy, and electrochemical oxidation potentials, determined by cyclic voltammetry, were lower for the 6-endomethylthio compounds than for their 6-exomethylthio analogues. Calculations supported the notion that facilitation of electron

  立体选择性地合成6-内和6-外甲硫基-2-内芳基双环[2.2.1]庚烷。通过光电子能谱测定的电离能和通过循环伏安法测定的电化学氧化电位比6-异甲硫基类似物低。计算结果支持6-内甲硫基化合物中电子的转移是通过空间S···π相互作用产生的。