(3S)-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one | 752207-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3S)-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one
• CAS: 752207-09-3
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: NKBYZJIWVZYHNB-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one 在 pyridinium hydrobromide perbromide 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 以71%的产率得到(3S)-1-bromo-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one
  参考文献：
  名称：

  Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol as a selective C17,20-lyase inhibitor

  摘要：

  An asymmetric synthesis of the selective C-17.20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral alpha-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.044
• 作为产物：
  描述：

  2,3-二甲氧基萘 在 三氯化铝 、 草酰氯 、 sodium hexamethyldisilazane 、 三乙胺 、 (-)-<(8,8-dichlorocamphoryl)sulfonyl>oxaziridine 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (3S)-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one
  参考文献：
  名称：

  Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol as a selective C17,20-lyase inhibitor

  摘要：

  An asymmetric synthesis of the selective C-17.20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral alpha-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.044