(3S)-1-bromo-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one | 752207-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3S)-1-bromo-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one
• 英文别名: (3S)-1-bromo-3-(6,7-dimethoxynaphthalen-2-yl)-3-hydroxy-4-methylpentan-2-one
• CAS: 752207-10-6
• 化学式: C₁₈H₂₁BrO₄
• 分子量: 381.266
• InChiKey: GKEMLJYKOSQNIT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-1-bromo-3-(6,7-dimethoxy-2-naphthyl)-3-hydroxy-4-methylpentan-2-one 在 2,6-二甲基吡啶 、 醋酸甲脒 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.5h， 生成 (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol
  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：

  1-(6,7-dimethoxy-2-naphthyl)propan-1-one 在 草酰氯 、 甲基磺酰胺 、 AD-mix-β 、 sodium hexamethyldisilazane 、 pyridinium hydrobromide perbromide 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 189.5h， 生成 (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

文献信息

• 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
  作者：Nobuyuki Matsunaga、Tomohiro Kaku、Akio Ojida、Akihiro Tasaka

  DOI：10.1016/j.tetasy.2004.05.044

  日期：2004.7

  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.