methyl (4R,5S,6Z)-4-chloro-5-hydroxy-7-phenylhept-6-enoate | 1220627-88-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: methyl (4R,5S,6Z)-4-chloro-5-hydroxy-7-phenylhept-6-enoate
• 英文别名: methyl (Z,4R,5S)-4-chloro-5-hydroxy-7-phenylhept-6-enoate
• CAS: 1220627-88-2
• 化学式: C₁₄H₁₇ClO₃
• 分子量: 268.74
• InChiKey: ZSZSLAGPXHMAJD-HYOAPIGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S,6Z)-4-chloro-5-hydroxy-7-phenylhept-6-enoate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以74%的产率得到methyl (4R,5S,6R,7R)-4-chloro-5,6,7-trihydroxy-7-phenylheptanoate
  参考文献：
  名称：

  Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans

  摘要：

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.

  DOI：

  10.1021/ol100260z
• 作为产物：
  描述：

  methyl (4S)-4-chloro-5-oxopentanoate 、 (Z)-styryl iodide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以88%的产率得到methyl (4R,5S,6Z)-4-chloro-5-hydroxy-7-phenylhept-6-enoate
  参考文献：
  名称：

  Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans

  摘要：

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.

  DOI：

  10.1021/ol100260z

文献信息

• Regioselective and Stereoselective Cyclizations of Chloropolyols in Water: Rapid Synthesis of Hydroxytetrahydrofurans
  作者：Baldip Kang、Stanley Chang、Shannon Decker、Robert Britton

  DOI：10.1021/ol100260z

  日期：2010.4.16

  A concise, stereoselective synthesis of functionalized tetrahydrofuranols has been developed that involves heating readily available chloropolyols in water. These reactions are operationally straightforward and chemoselective for the formation of tetrahydrofurans, obviating the need for complicated protecting group strategies. The efficiency of this process is demonstrated in a short asymmetric synthesis of the natural product (+)-goniothalesdiol.