[(1S,2S,5R)-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl]methyl 4-methylbenzenesulfonate | 157523-16-5

• 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: [(1S,2S,5R)-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 157523-16-5
• 化学式: C₁₃H₁₄O₅S
• 分子量: 282.317
• InChiKey: CPAGCZWKMQIIIJ-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1S,2S,5R)-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl]methyl 4-methylbenzenesulfonate 在 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 cis-2-Vinyl-cyclopropancarbonsaeuremethylester
  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 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [(1S,2S,5R)-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  甲基的合成（1 - [R，2小号）-2 - [（1' Ž，4' Ž，7' Ž） -十六碳1'，4'，7'-三烯基]环丙烷羧酸甲酯：所述酶5的潜在的抑制剂脂氧合酶

  摘要：

  我们描述了一种新的花生四烯酸环丙基类似物的合成，该合成通过使用（1 R，2 S）-2-甲酰基环丙烷甲酸甲酯与（3 Z，6 Z）-pentadeca-3,6-的叶立德一起使用的会聚合成来合成。二烯基（三苯基）碘化.。该化合物被设计成在反应形成抑制的α-环丙基亚甲基后抑制酶5-脂氧合酶。

  DOI：

  10.1039/p19940001503

文献信息

• Synthesis of methyl (1R,2S)-2-[(1′Z,4′Z,7′Z)-hexadeca-1′,4′,7′-trienyl]cyclopropanecarboxylate: a potential inhibitor of the enzyme 5-lipoxygenase
  作者：Paul I. Butler、Trafford Clarke、Colin Dell、John Mann

  DOI：10.1039/p19940001503

  日期：——

  We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)phosphonium iodide. This compound was designed to inhibit the enzyme 5-lipoxygenase after reaction to form a putative α-cyclopropylmethylene radical.

  我们描述了一种新的花生四烯酸环丙基类似物的合成，该合成通过使用（1 R，2 S）-2-甲酰基环丙烷甲酸甲酯与（3 Z，6 Z）-pentadeca-3,6-的叶立德一起使用的会聚合成来合成。二烯基（三苯基）碘化.。该化合物被设计成在反应形成抑制的α-环丙基亚甲基后抑制酶5-脂氧合酶。
• 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.