(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(6-methoxy-2-naphthyl)-2-methyl-2-propen-1-ol | 727722-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(6-methoxy-2-naphthyl)-2-methyl-2-propen-1-ol
• 英文别名: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(6-methoxynaphthalen-2-yl)-2-methylprop-2-en-1-ol
• CAS: 727722-99-8
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: MYBSKWWNRDPSKO-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(6-methoxy-2-naphthyl)-2-methyl-2-propen-1-ol 在 palladium on activated charcoal 吡啶 、 盐酸 、 草酰氯 、 氨 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， -70.0~60.0 ℃ 、101.33 kPa 条件下， 反应 38.0h， 生成 (6-methoxy-2-naphthyl) isopropyl ketone
  参考文献：
  名称：

  Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

  摘要：

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.035
• 作为产物：
  描述：

  [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-morpholin-4-ylmethanone 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.66h， 生成 (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(6-methoxy-2-naphthyl)-2-methyl-2-propen-1-ol
  参考文献：
  名称：

  Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

  摘要：

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.035

文献信息

• Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor
  作者：Akio Ojida、Nobuyuki Matsunaga、Tomohiro Kaku、Akihiro Tasaka

  DOI：10.1016/j.tetasy.2004.02.035

  日期：2004.5

  An efficient stereocontrolled synthesis of the Potent C-17.20-lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1-propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale. (C) 2004 Elsevier Ltd. All rights reserved.