(1R,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one | 159950-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one
• CAS: 159950-60-4
• 化学式: C₆H₇IO₂
• 分子量: 238.025
• InChiKey: XMSFZDFDYFDCKP-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one 在 二异丁基氢化铝 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 cis-2-Vinylcyclopropanmethanol
  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 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 30.67h， 生成 (1R,4S,5S)-4-(iodomethyl)-3-oxabicyclo[3.1.0]hexan-2-one
  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

• Stereoselective synthesis of enantiopure cyclopropane didehydroamino acid derivatives: (−)-(Z)-2-Benzyloxycarbonylamino-4,5-cyclopropane-2-hexenodioic acid dimethyl ester
  作者：Neuh Hanafi、Rosa M. Ortuño

  DOI：10.1016/0957-4166(94)80074-x

  日期：1994.9

  The title amino acid derivative has been synthesized stereoselectively in 40% overall yield from 5-tert-butyldiphenylsilyloxymethyl-2(5H)-furanone used as a chiral precursor.
• 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
  作者：Marta Martín-Vilà、Neuh Hanafi、José M. Jiménez、Angel Alvarez-Larena、Joan F. Piniella、Vicenç Branchadell、Antonio Oliva、Rosa M. Ortuño

  DOI：10.1021/jo972219a

  日期：1998.5.1

  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.