(1S,8aS)-5-Hydroxymethyl-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol | 474956-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,8aS)-5-Hydroxymethyl-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol
• 英文别名: (1S,8aS)-5-(hydroxymethyl)-8a-methyl-2,3,4,6,7,8-hexahydro-1H-naphthalen-1-ol
• CAS: 474956-32-6
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: SSKDUFMZNXMGLK-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 (1S,8aS)-5-Hydroxymethyl-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol 在 吡啶 作用下， 反应 19.0h， 以26.0 mg的产率得到
  参考文献：
  名称：

  Asymmetric construction of novel bicyclo[4.4.0] and [4.3.0]ring systems via intramolecular Horner–Wadsworth–Emmons reactions

  摘要：

  Novel perhydro-indanones and -naphthalenones having a quaternary stereogenic carbon and tetrasubstituted olefinic linkage were prepared via asymmetric intramolecular Horner-Wadsworth-Emmons reactions. The optically active binaphthyl phosphonates were connected with the 2-substituted cyclopenta- or cyclohexa-1,3-dione through the linker arm and the successive base treatment of the products with diethylzinc led to cyclization reactions with concomitant differentiation of diastereotopic carbonyl groups to afford the non-racemic title compounds in good enantiomeric excess. The absolute structure of the cyclized product was determined by X-ray analysis of its derived bromide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00177-5
• 作为产物：
  描述：

  2-甲基-1,3-环己二酮 在 高氯酸 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 diethylzinc 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 106.5h， 生成 (1S,8aS)-5-Hydroxymethyl-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol
  参考文献：
  名称：

  Asymmetric construction of novel bicyclo[4.4.0] and [4.3.0]ring systems via intramolecular Horner–Wadsworth–Emmons reactions

  摘要：

  Novel perhydro-indanones and -naphthalenones having a quaternary stereogenic carbon and tetrasubstituted olefinic linkage were prepared via asymmetric intramolecular Horner-Wadsworth-Emmons reactions. The optically active binaphthyl phosphonates were connected with the 2-substituted cyclopenta- or cyclohexa-1,3-dione through the linker arm and the successive base treatment of the products with diethylzinc led to cyclization reactions with concomitant differentiation of diastereotopic carbonyl groups to afford the non-racemic title compounds in good enantiomeric excess. The absolute structure of the cyclized product was determined by X-ray analysis of its derived bromide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00177-5