(2-Hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)-acetonitrile | 360077-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-Hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)-acetonitrile
• 英文别名: 2-[(1R,2R,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]acetonitrile
• CAS: 360077-91-4
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: QPZPXIQHAKHSPV-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-Hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)-acetonitrile 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到(4-Bromo-2-hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)acetonitrile
  参考文献：
  名称：

  New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions

  摘要：

  A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.

  DOI：

  10.1002/1521-3765(20010601)7:11<2349::aid-chem23490>3.0.co;2-c
• 作为产物：
  描述：

  2-[(1S,2S,3S,7R,8R,9S)-3-hydroxy-8-(4-methoxyphenyl)-9-methyl-6-oxo-3-tetracyclo[6.5.2.01,9.02,7]pentadeca-4,14-dienyl]acetonitrile 在 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (2-Hydroxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-2-yl)-acetonitrile
  参考文献：
  名称：

  New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions

  摘要：

  A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.

  DOI：

  10.1002/1521-3765(20010601)7:11<2349::aid-chem23490>3.0.co;2-c

文献信息

• New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions
  作者：Marie-Elise Trân-Huu-Dâu、Rudolf Wartchow、Ekkehard Winterfeldt、Yung-Sing Wong

  DOI：10.1002/1521-3765(20010601)7:11<2349::aid-chem23490>3.0.co;2-c

  日期：2001.6.1

  A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.