(1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropanecarboxylic acid methyl ester | 167699-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropanecarboxylic acid methyl ester
• 英文别名: methyl (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylate
• CAS: 167699-79-8
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: WXNMYVLPXQFNCQ-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropanecarboxylic acid methyl ester 在 n-Bu₄IO₄ 、 溶剂黄146 作用下， 生成 甲基(1S,2R)-2-甲酰基环丙烷羧酸酯
  参考文献：
  名称：

  Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones:  Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

  摘要：

  The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since pi-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open-chain structures, enantiomeric series of products can be derived.

  DOI：

  10.1021/jo972219a
• 作为产物：
  描述：

  methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 以 乙醚 、 丙酮 为溶剂， 反应 18.0h， 生成 (1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones:  Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

  摘要：

  The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since pi-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open-chain structures, enantiomeric series of products can be derived.

  DOI：

  10.1021/jo972219a