(1R,3R,5R,6S)-3,6-bis-[di(4'-methoxyphenyl)phosphinooxy]-bicyclo[3.2.0]heptane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,3R,5R,6S)-3,6-bis-[di(4'-methoxyphenyl)phosphinooxy]-bicyclo[3.2.0]heptane
• 英文别名: [(1R,3R,5R,6S)-3-bis(4-methoxyphenyl)phosphanyloxy-6-bicyclo[3.2.0]heptanyl]oxy-bis(4-methoxyphenyl)phosphane
• 化学式: C₃₅H₃₈O₆P₂
• 分子量: 616.631
• InChiKey: VPZTVYOUJXZQJE-ONAJPNPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1R,2S,3S,5R)-(-)-2-bromo-3-hydroxy-bicyclo[3.2.0]heptan-6-one 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 18.0h， 生成 (1R,3R,5R,6S)-3,6-bis-[di(4'-methoxyphenyl)phosphinooxy]-bicyclo[3.2.0]heptane
  参考文献：
  名称：

  Asymmetric hydrogenation reactions mediated by a new class of bicyclic bisphosphinites

  摘要：

  The bicyclic alcohol (-)-4 was prepared from (-)-bicyclo[3.2.0]hept-2-en-6-one (-)-1 in 50% yield. The diol (-)-4 was coupled to selected chlorophosphines 6-12 to produce a series of bisphosphinites 13-19 in 89-95% yield. From these bisphosphinites were prepared the rhodium complexes 20-26 which were characterised by P-31 NMR and used in situ for the asymmetric hydrogenation of alpha-enamides 27-29. Complexes 21, 23-25 proved to be the superior catalysts for the production of (R)-N-acetylphenylalanine (91, 84, 90 and 87.5% ee) from 27 and (S)-N-acetylalanine methyl ester (70, 72, 68 and 71% ee) from 28. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00341-9