ethyl (1RS,2RS)-1-(1-ethyl-1-hydroxypropyl)-2-phenylcyclopropanecarboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1RS,2RS)-1-(1-ethyl-1-hydroxypropyl)-2-phenylcyclopropanecarboxylate
• 英文别名: ethyl (1R,2R)-1-(3-hydroxypentan-3-yl)-2-phenylcyclopropane-1-carboxylate
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: PWGXFZLCZIQWSP-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-ethyl 1-chloro-2-phenylcyclopropanecarboxylate 、 3-戊酮 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到ethyl (1RS,2RS)-1-(1-ethyl-1-hydroxypropyl)-2-phenylcyclopropanecarboxylate
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates

  摘要：

  In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).

  DOI：

  10.1021/ol8022038

文献信息

• SmI₂-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates
  作者：Takao Nagano、Jiro Motoyoshiya、Akikazu Kakehi、Yoshinori Nishii

  DOI：10.1021/ol8022038

  日期：2008.12.4

  In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).