(2R,3S)-3-(6,7-dimethoxy-2-naphthyl)-4-methylpentane-2,3-diol | 752207-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S)-3-(6,7-dimethoxy-2-naphthyl)-4-methylpentane-2,3-diol
• 英文别名: (2R,3S)-3-(6,7-dimethoxynaphthalen-2-yl)-4-methylpentane-2,3-diol
• CAS: 752207-08-2
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: LUCIXVCNGQGESN-KZULUSFZSA-N

物化性质

• 熔点：
  99.5-100.5 °C(Solv: isopropyl ether (108-20-3); ethyl ether (60-29-7))
• 沸点：
  475.7±40.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(6,7-dimethoxy-2-naphthyl)-4-methylpentane-2,3-diol 在 草酰氯 、 pyridinium hydrobromide perbromide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.5h， 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
• 作为产物：
  描述：

  1-(6,7-dimethoxy-2-naphthyl)propan-1-one 在 sodium hexamethyldisilazane 、 (-)-<(8,8-dichlorocamphoryl)sulfonyl>oxaziridine 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 (2R,3S)-3-(6,7-dimethoxy-2-naphthyl)-4-methylpentane-2,3-diol
  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.