2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfide | 246862-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfide
• 英文别名: 4-Methyl-1-[2-[2,4,6-tri(propan-2-yl)phenyl]sulfanylethyl]-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 246862-24-8
• 化学式: C₂₃H₃₆O₃S
• 分子量: 392.603
• InChiKey: LJTCZAJPCTYAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfide 在 (+)-N-(phenylsulfonyl)camphoroxaziridine 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 以55%的产率得到(S)-2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfoxide
  参考文献：
  名称：

  A convergent asymmetric synthesis of γ-butenolides

  摘要：

  The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded gamma -butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of gamma -butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00078-3
• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfide
  参考文献：
  名称：

  A convergent asymmetric synthesis of γ-butenolides

  摘要：

  Addition of aldehydes to the new enantiomerically pure lithiated sulfoxide 4 yielded gamma-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The reaction with ketones was less stereoselective. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01242-3