Acetic acid (3aS,4S,7aS)-7-bromo-2,2-dimethyl-5-oxo-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester | 596834-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3aS,4S,7aS)-7-bromo-2,2-dimethyl-5-oxo-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester
• CAS: 596834-75-2
• 化学式: C₁₁H₁₃BrO₅
• 分子量: 305.125
• InChiKey: YGKCOEQUBBBXQS-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aS,4S,7aS)-7-bromo-2,2-dimethyl-5-oxo-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以40%的产率得到Acetic acid (3aR,4S,7aR)-2,2-dimethyl-5-oxo-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5
• 作为产物：
  描述：

  [3aS-(3aα,4α,5α,7aα)]-7-溴-3a,4,5,7a-四氢-2,2-二甲基-1,3-苯并二茂-4,5-二醇 在 吡啶 、 4-二甲氨基吡啶 、 重铬酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (3aS,4S,7aS)-7-bromo-2,2-dimethyl-5-oxo-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5