[(1R,2R)-2-ethenylcyclopropyl]methyl benzoate | 206982-02-7

• 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: [(1R,2R)-2-ethenylcyclopropyl]methyl benzoate
• CAS: 206982-02-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: VUNRZMBEOFCZLI-JQWIXIFHSA-N

物化性质

• 沸点：
  278.7±9.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  [(1R,2R)-2-ethenylcyclopropyl]methyl benzoate 在 二甲基硫 、 臭氧 作用下， 生成 Benzoic acid (1R,2S)-2-formyl-cyclopropylmethyl 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
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 二异丁基氢化铝 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 32.42h， 生成 [(1R,2R)-2-ethenylcyclopropyl]methyl benzoate
  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

文献信息

• Olefin cross-metathesis in the preparation of polycyclopropanes: formal synthesis of FR-900848
  作者：Christopher A Verbicky、Charles K Zercher

  DOI：10.1016/s0040-4039(00)01568-9

  日期：2000.11

  Olefin cross-metathesis was used for the efficient incorporation of an E-olefin between two cyclopropane residues. The generation of a bis-cyclopropyl alkene homodimer, followed by cross metathesis with a terminal vinyl polycyclopropane, provided excellent yields of the targeted compounds with good olefin stereoselectivity. The strategy was applied to generation of a quinta-cyclopropane intermediate

  烯烃交叉复分解用于在两个环丙烷残基之间有效地引入E-烯烃。生成双环丙基烯烃均二聚体，然后与末端乙烯基聚环丙烷进行交叉复分解，可提供优异的目标化合物收率，并具有良好的烯烃立体选择性。该策略被用于生成天然产物FR-900848的先前合成中发现的喹啉-环丙烷中间体。