1-deuterio-2-(2-methylthioethyl)-3-methyl-2-cyclohexenol | 148043-38-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deuterio-2-(2-methylthioethyl)-3-methyl-2-cyclohexenol
• CAS: 148043-38-3
• 化学式: C₁₀H₁₈OS
• 分子量: 187.31
• InChiKey: SAJHHPGYGZOKDS-MMIHMFRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(氯甲基)-4-硝基苯 、 1-deuterio-2-(2-methylthioethyl)-3-methyl-2-cyclohexenol 在 吡啶 作用下， 以91.7%的产率得到1-deuterio-2-(2-methylthioethyl)-3-methyl-2-cyclohexenyl p-nitrobenzoate
  参考文献：
  名称：

  A search for maximal neighboring group participation in Solvolyses of allylic substrates. Ethanolysis of 2-(ω-alkylthioalkyl)-3-methyl-2-cyclohexenyl p-nitrobenzoates

  摘要：

  The solvolysis of 2-(omega-methylthioalkyl)- and 2-(omega-benzylthioalkyl)-3-methyl-2-cyclohexenyl p-nitrobenzoates 5 and 6 in 80 vol % ethanol includes several competitive reactions. Path k1 is a stepwise process (k(H)/k(D) = 1.18-1.20) which includes allylic cation 9 as a reaction intermediate, while path k2 involves a neighboring sulfur participation (k(H)/k(D) = 1.01 - 1.03) and formation of an intermediate cyclic sulfonium cation 10. Esters 5 and 6 solvolyze in 80% EtOH with a greater neighboring group participation than in 97% TFE. IL has been concluded that in solvolytic reactions of allylic substrates a pronounced neighboring group participation (k2/k1= 900) may occur only with very strong internal nucleophiles, and in solvents which can not form strong hydrogen bonds with these nucleophiles.

  DOI：

  10.1016/s0040-4020(01)86349-3
• 作为产物：
  描述：

  在 氢氧化钾 、 lithium aluminium deuteride 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-deuterio-2-(2-methylthioethyl)-3-methyl-2-cyclohexenol
  参考文献：
  名称：

  A search for maximal neighboring group participation in Solvolyses of allylic substrates. Ethanolysis of 2-(ω-alkylthioalkyl)-3-methyl-2-cyclohexenyl p-nitrobenzoates

  摘要：

  The solvolysis of 2-(omega-methylthioalkyl)- and 2-(omega-benzylthioalkyl)-3-methyl-2-cyclohexenyl p-nitrobenzoates 5 and 6 in 80 vol % ethanol includes several competitive reactions. Path k1 is a stepwise process (k(H)/k(D) = 1.18-1.20) which includes allylic cation 9 as a reaction intermediate, while path k2 involves a neighboring sulfur participation (k(H)/k(D) = 1.01 - 1.03) and formation of an intermediate cyclic sulfonium cation 10. Esters 5 and 6 solvolyze in 80% EtOH with a greater neighboring group participation than in 97% TFE. IL has been concluded that in solvolytic reactions of allylic substrates a pronounced neighboring group participation (k2/k1= 900) may occur only with very strong internal nucleophiles, and in solvents which can not form strong hydrogen bonds with these nucleophiles.

  DOI：

  10.1016/s0040-4020(01)86349-3