tert-butyl (RS)-6-ethyl-cyclohex-1-ene-carboxylate | 1138336-93-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (RS)-6-ethyl-cyclohex-1-ene-carboxylate
• 英文别名: Tert-butyl 6-ethylcyclohexene-1-carboxylate；tert-butyl 6-ethylcyclohexene-1-carboxylate
• CAS: 1138336-93-2
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: COKWNDUGZNEDCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (RS)-6-ethyl-cyclohex-1-ene-carboxylate 、 N-苄基异丙胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以77%的产率得到tert-butyl (1RS,2SR,6RS)-2-[N-benzyl-N-isopropylamino]-6-ethyl-cyclohexane-carboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

  摘要：

  Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.019
• 作为产物：
  描述：

  tert-butyl (RS)-6-acetoxy-cyclohex-1-ene-carboxylate 、 乙基氯化镁 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到tert-butyl (RS)-6-ethyl-cyclohex-1-ene-carboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

  摘要：

  Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.019

文献信息

• Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives
  作者：Stephen G. Davies、Matthew J. Durbin、Scott J.S. Hartman、Ai Matsuno、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson、Steven M. Toms

  DOI：10.1016/j.tetasy.2008.11.019

  日期：2008.12

  Excellent levels of enantiorecognition are displayed by tert-butyl (RS)-6-n-alkyl-cyclohex-1-ene-carboxylates in mutual kinetic resolutions with lithium (RS)-N-benzyl]-N-(alpha-methylbenzyl)amide. Therefore a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide allows their efficient parallel kinetic resolution, affording differentially protected 6-n-alkyl-cishexacin derivatives in high yield and >95% de. N-Debenzylation and ester hydrolysis give access to the corresponding homochiral 6-n-alkyl-substituted cishexacin derivatives. (C) 2008 Elsevier Ltd. All rights reserved.