(S)-3-((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-butyronitrile | 135323-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-3-((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-butyronitrile
• CAS: 135323-34-1
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: KESWKBWSIQBKNT-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-butyronitrile 在 sodium tetrahydroborate 、 甲烷磺酸 、 叔丁基锂 、 sodium acetate 、 四氯化锡 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 7.25h， 生成 (1R,3S,3aR)-7-Methoxy-3,9-dimethyl-2,3,3a,4,5,6-hexahydro-1H-phenalene-1-carbonitrile
  参考文献：
  名称：

  Controlling benzylic functionality and stereochemistry: 2. Synthesis of the pseudopterosin aglycone

  摘要：

  Homologation, cyclisation, and reduction converted the tetralin (2) to the hexahydrophenalenol (8), which was methylated to afford (19) via alkoxide-directed metalation. The degree of stereoselectivity resulting from reactions of (19) and congeners with allylsilane - Lewis acid combinations was markedly dependent upon substitution patterns, whereas Et2AlCN-SnCl4 produced pseudoaxial nitriles. The trimethyl nitrile (24) was elaborated to the pseudopterosin aglycone (4).

  DOI：

  10.1016/s0040-4039(00)71243-3
• 作为产物：
  描述：

  (R)-2-((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-propan-1-ol 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-3-((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-butyronitrile
  参考文献：
  名称：

  Controlling benzylic functionality and stereochemistry: 2. Synthesis of the pseudopterosin aglycone

  摘要：

  Homologation, cyclisation, and reduction converted the tetralin (2) to the hexahydrophenalenol (8), which was methylated to afford (19) via alkoxide-directed metalation. The degree of stereoselectivity resulting from reactions of (19) and congeners with allylsilane - Lewis acid combinations was markedly dependent upon substitution patterns, whereas Et2AlCN-SnCl4 produced pseudoaxial nitriles. The trimethyl nitrile (24) was elaborated to the pseudopterosin aglycone (4).

  DOI：

  10.1016/s0040-4039(00)71243-3