2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfoxide | 342885-80-7

• 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 sulfoxide
• 英文别名: 4-Methyl-1-[2-[2,4,6-tri(propan-2-yl)phenyl]sulfinylethyl]-2,6,7-trioxabicyclo[2.2.2]octane；4-methyl-1-[2-[2,4,6-tri(propan-2-yl)phenyl]sulfinylethyl]-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 342885-80-7
• 化学式: C₂₃H₃₆O₄S
• 分子量: 408.602
• InChiKey: BZYVEUIBZLDBMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 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：
  64
• 氢给体数：
  0
• 氢受体数：
  5

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 sulfoxide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成
  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：

  2,4,6-Triisopropylthiophenol 在 lithium hydroxide 、 三氟化硼乙醚 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 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

文献信息

• A convergent asymmetric synthesis of γ-butenolides
  作者：Marc Renard、Léon A. Ghosez

  DOI：10.1016/s0040-4020(01)00078-3

  日期：2001.3

  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.