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 | 360077-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 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
• CAS: 360077-80-1
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: NSIYMCGMJJNKSX-UJXAWSPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 、 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (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：

  (1-Hydroxy-4-oxo-cyclohexa-2,5-dienyl)acetonitrile 、 (7aS)-1-(4-methoxyphenyl)-7a-methyl-4,5,6,7-tetrahydroindene 以 二氯甲烷 为溶剂， 20.0 ℃ 、1400.03 MPa 条件下， 反应 144.0h， 以89%的产率得到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
  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.