ethyl (Z)-2-[(1R)-1-hydroxy-3-phenylmethoxypropyl]pent-2-enoate | 1224142-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (Z)-2-[(1R)-1-hydroxy-3-phenylmethoxypropyl]pent-2-enoate
• CAS: 1224142-59-9
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: IEHRPIZCLRWGJC-MVMZHWFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Ethyl 2-bromopent-2-enoate 、 3-苄氧基丙醛 在 chromium dichloride 、 三乙胺 、 nickel dichloride 、 艾日布林S-甲基配体 、 乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 ethyl (Z)-2-[(1R)-1-hydroxy-3-phenylmethoxypropyl]pent-2-enoate 、 ethyl (Z)-2-[(1S)-1-hydroxy-3-phenylmethoxypropyl]pent-2-enoate
  参考文献：
  名称：

  An asymmetric nickel–chromium coupling toward the synthesis of Baylis–Hillman adducts

  摘要：

  An asymmetric nickel-chromium coupling strategy has been employed in the generation of enantioenriched Baylis-Hillman adducts with selectivities reaching >90% ee and in fair to moderate yields (up to 65%) using a chiral sulfonamide ligand. The reaction conditions appear to show reasonable generality and are compatible with both aromatic and aliphatic aldehydes. Utilizing such a strategy not only allows for the preparation of products which contain substitution at the beta-position on the olefin but also allows for the separation of olefin isomers in this transformation. (c) 2010 Elsevier Ltd. All rights received.

  DOI：

  10.1016/j.tetlet.2010.02.078

文献信息

• An asymmetric nickel–chromium coupling toward the synthesis of Baylis–Hillman adducts
  作者：Francis G. Fang、Thomas E. Horstmann、Jonathan Therrien

  DOI：10.1016/j.tetlet.2010.02.078

  日期：2010.4

  An asymmetric nickel-chromium coupling strategy has been employed in the generation of enantioenriched Baylis-Hillman adducts with selectivities reaching >90% ee and in fair to moderate yields (up to 65%) using a chiral sulfonamide ligand. The reaction conditions appear to show reasonable generality and are compatible with both aromatic and aliphatic aldehydes. Utilizing such a strategy not only allows for the preparation of products which contain substitution at the beta-position on the olefin but also allows for the separation of olefin isomers in this transformation. (c) 2010 Elsevier Ltd. All rights received.