methyl (3R,4S)-4-(chloromethyl)-2-oxooxolane-3-carboxylate | 1333379-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl (3R,4S)-4-(chloromethyl)-2-oxooxolane-3-carboxylate
• CAS: 1333379-12-6
• 化学式: C₇H₉ClO₄
• 分子量: 192.599
• InChiKey: MFDIMGOFSMBTCZ-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S)-4-(chloromethyl)-2-oxooxolane-3-carboxylate 在 iron(III) trifluoride 、 triethylamine tris(hydrogen fluoride) 作用下， 反应 168.0h， 生成 (S)-4-fluoromethyldihydro-3H-furan-2-one
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k
• 作为产物：
  描述：

  丙二酸二甲酯 在 盐酸 、 aluminum (III) chloride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 methyl (3R,4S)-4-(chloromethyl)-2-oxooxolane-3-carboxylate
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k

文献信息

• Development of a Scalable Synthesis of (<i>S</i>)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety
  作者：Jean-Michel Adam、Joseph Foricher、Steven Hanlon、Bruno Lohri、Gérard Moine、Rudolf Schmid、Helmut Stahr、Martin Weber、Beat Wirz、Ulrich Zutter

  DOI：10.1021/op200019k

  日期：2011.5.20

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.