(3R,4S,4aR,8aS)-3,4-O-isopropylidene-3,4-dihydroxy-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone | 130097-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,4aR,8aS)-3,4-O-isopropylidene-3,4-dihydroxy-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone
• 英文别名: (3aR,5aS,9aR,9bS)-2,2-dimethyl-4,5a,6,9,9a,9b-hexahydro-3aH-naphtho[1,2-d][1,3]dioxol-5-one
• CAS: 130097-04-0
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: YIUDXTAWSCUIGR-SPFNVWMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,4aR,8aS)-3,4-O-isopropylidene-3,4-dihydroxy-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone 在 sodium dithionite 、 甲基三辛基氯化铵 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 苯 为溶剂， 反应 8.0h， 生成 (4S,4aS)-4-(tert-Butyl-dimethyl-silanyloxy)-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  On the diastereofacial selectivity of Lewis acid-catalyzed carbon-carbon bond forming reactions of conjugated cyclic enones bearing electron-withdrawing substituents at the .gamma.-position

  摘要：

  Lewis acid catalyzed reactions of several cyclic enones are described. The gamma-OTBS enones 1 and 2 give products where carbon-carbon bond formation at the beta carbon occurs with high stereoselectivity favoring attack syn to the resident OTBS group. In the case of enone 24 bearing an additional dioxolane ring, the products correspond to addition anti to the resident carbon-oxygen bond at the gamma carbon. The reaction of 24 with lithium dimethylcuprate also occurs in an anti sense. The starting materials in this study are available in quantity in optically pure form. Given the excellent stereoselectivity of the reactions, these compounds are useful intermediates for synthesis.

  DOI：

  10.1021/jo00001a070
• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 、 1,3-丁二烯 、 三氯化铝 生成 (3R,4S,4aR,8aS)-3,4-O-isopropylidene-3,4-dihydroxy-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone
  参考文献：
  名称：

  JERONCIC, LUCIO O.;CABAL, MARIA-PAZ;DANISHEFSKY, SAMUEL J.;SHULTE, GAYLE +, J. ORG. CHEM., 56,(1991) N, C. 387-395

  摘要：

  DOI：

文献信息

• JERONCIC, LUCIO O.;CABAL, MARIA-PAZ;DANISHEFSKY, SAMUEL J.;SHULTE, GAYLE +, J. ORG. CHEM., 56,(1991) N, C. 387-395
  作者：JERONCIC, LUCIO O.、CABAL, MARIA-PAZ、DANISHEFSKY, SAMUEL J.、SHULTE, GAYLE +

  DOI：——

  日期：——
• On the diastereofacial selectivity of Lewis acid-catalyzed carbon-carbon bond forming reactions of conjugated cyclic enones bearing electron-withdrawing substituents at the .gamma.-position
  作者：Lucio O. Jeroncic、Maria Paz Cabal、Samuel J. Danishefsky、Gayle M. Shulte

  DOI：10.1021/jo00001a070

  日期：1991.1

  Lewis acid catalyzed reactions of several cyclic enones are described. The gamma-OTBS enones 1 and 2 give products where carbon-carbon bond formation at the beta carbon occurs with high stereoselectivity favoring attack syn to the resident OTBS group. In the case of enone 24 bearing an additional dioxolane ring, the products correspond to addition anti to the resident carbon-oxygen bond at the gamma carbon. The reaction of 24 with lithium dimethylcuprate also occurs in an anti sense. The starting materials in this study are available in quantity in optically pure form. Given the excellent stereoselectivity of the reactions, these compounds are useful intermediates for synthesis.