[1R-(1α(2E,4R^*),3aβ,4α,7aα)]-4-[4-(benzyloxy)octahydro-7a-methyl-1H-inden-1-yl]-2-penten-1-al

• 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: [1R-(1α(2E,4R^*),3aβ,4α,7aα)]-4-[4-(benzyloxy)octahydro-7a-methyl-1H-inden-1-yl]-2-penten-1-al
• 英文别名: [(1R,3aR,4S,7aR)-7a-methyl-1-[(E,2R)-5-oxopent-3-en-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: NPJKAAHLPHSORO-HAHBAJLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1R-(1α(2E,4R^*),3aβ,4α,7aα)]-4-[4-(benzyloxy)octahydro-7a-methyl-1H-inden-1-yl]-2-penten-1-al 在 lanthanum(III) isopropoxide 、 偶氮二异丁腈 、 (S)-6,6'-bis((trimethylsilyl)ethynyl)BINOL 、 potassium tert-butylate 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 98.0h， 生成 [1R-(1α(3R^*,4E,6R^*),3aβ,4α,7aα)]-6-[4-(benzyloxy)octahydro-7a-methyl-1H-inden-1-yl]-2-methyl-2-nitro-4-hepten-3-ol
  参考文献：
  名称：

  Novel synthetic approach to 1α,24(R)-dihydroxyvitamin D3 using an asymmetric nitroaldol reaction

  摘要：

  Rare earth-K-(S)-BINOL complexes were used to catalyze the nitroaldol reaction of the CD-ring 24-aldehyde precursors with 2-nitropropane in a good stereoselective manner. The obtained nitroaldol compound was easily converted into a synthetic intermediate 12 of 1 alpha,24(R)-dihydroxyvitamin D-3 1 by a denitration reaction using 2,2'-azobisisobutyronitrile (AIBN) and Bu3SnH. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00312-1

文献信息

• Novel synthetic approach to 1α,24(R)-dihydroxyvitamin D3 using an asymmetric nitroaldol reaction
  作者：Jun-ichi Oshida、Makoto Okamoto、Shizuo Azuma、Toshio Tanaka

  DOI：10.1016/s0957-4166(97)00312-1

  日期：1997.8

  Rare earth-K-(S)-BINOL complexes were used to catalyze the nitroaldol reaction of the CD-ring 24-aldehyde precursors with 2-nitropropane in a good stereoselective manner. The obtained nitroaldol compound was easily converted into a synthetic intermediate 12 of 1 alpha,24(R)-dihydroxyvitamin D-3 1 by a denitration reaction using 2,2'-azobisisobutyronitrile (AIBN) and Bu3SnH. (C) 1997 Elsevier Science Ltd.