(4S,5S)-2-[(4S)-4,5-dimethyl-3,6-diphenyl-1-phosphabicyclo[2.2.1]hepta-2,5-dien-2-yl]-4,5-diphenyl-1,3-dioxolane | 268552-25-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5S)-2-[(4S)-4,5-dimethyl-3,6-diphenyl-1-phosphabicyclo[2.2.1]hepta-2,5-dien-2-yl]-4,5-diphenyl-1,3-dioxolane
• CAS: 268552-25-6
• 化学式: C₃₅H₃₁O₂P
• 分子量: 514.604
• InChiKey: PJQDHUXUAWECMI-DASPPZQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-2-[(4S)-4,5-dimethyl-3,6-diphenyl-1-phosphabicyclo[2.2.1]hepta-2,5-dien-2-yl]-4,5-diphenyl-1,3-dioxolane 在 盐酸 、 silica gel 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (1R)-2,5-diphenyl-3,4-dimethyl-6-formyl-1-phosphanorborna-2,5-diene
  参考文献：
  名称：

  Enantiopure 1-phosphanorbornadiene-2-carboxaldehydes

  摘要：

  The reaction of phenylpropargyl aldehyde diethyl acetal with 1-phenyl-3,4-dimethylphosphole at 140 degreesC or 1,2,5-triphenylphosphole at 170 degreesC leads, after deprotection, to the corresponding 1-phosphanorbornadiene-2-carboxaldehydes 3 and 4 in 88 and 45% yields, respectively. The resolution of 3 and 4 was carried out by chromatography or fractional crystallization of the acetals derived from (S,S)-1,2-diphenylethane-1,2-diol. The absolute configurations were established by X-ray analysis of one of these acetals or of a 2-bromomethyl derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00443-2
• 作为产物：
  描述：

  苯丙炔醛缩二乙醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 7.25h， 生成 (4S,5S)-2-[(4S)-4,5-dimethyl-3,6-diphenyl-1-phosphabicyclo[2.2.1]hepta-2,5-dien-2-yl]-4,5-diphenyl-1,3-dioxolane
  参考文献：
  名称：

  Enantiopure 1-phosphanorbornadiene-2-carboxaldehydes

  摘要：

  The reaction of phenylpropargyl aldehyde diethyl acetal with 1-phenyl-3,4-dimethylphosphole at 140 degreesC or 1,2,5-triphenylphosphole at 170 degreesC leads, after deprotection, to the corresponding 1-phosphanorbornadiene-2-carboxaldehydes 3 and 4 in 88 and 45% yields, respectively. The resolution of 3 and 4 was carried out by chromatography or fractional crystallization of the acetals derived from (S,S)-1,2-diphenylethane-1,2-diol. The absolute configurations were established by X-ray analysis of one of these acetals or of a 2-bromomethyl derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00443-2

文献信息

• Enantiopure 1-phosphanorbornadiene-2-carboxaldehydes
  作者：Stèphane Lelièvre、François Mercier、Louis Ricard、François Mathey

  DOI：10.1016/s0957-4166(00)00443-2

  日期：2000.11

  The reaction of phenylpropargyl aldehyde diethyl acetal with 1-phenyl-3,4-dimethylphosphole at 140 degreesC or 1,2,5-triphenylphosphole at 170 degreesC leads, after deprotection, to the corresponding 1-phosphanorbornadiene-2-carboxaldehydes 3 and 4 in 88 and 45% yields, respectively. The resolution of 3 and 4 was carried out by chromatography or fractional crystallization of the acetals derived from (S,S)-1,2-diphenylethane-1,2-diol. The absolute configurations were established by X-ray analysis of one of these acetals or of a 2-bromomethyl derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.