methyl 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: methyl 1-(1-ethyl-1-hydroxypropyl)-2-phenylcyclopropanecarboxylate
• 英文别名: methyl (1RS,2RS)-1-(1-ethyl-1-hydroxypropyl)-2-phenylcyclopropanecarboxylate；methyl (1R,2R)-1-(3-hydroxypentan-3-yl)-2-phenylcyclopropane-1-carboxylate
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: ONYJHMXAORMEKC-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  methyl 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77%的产率得到methyl 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

• Highly Stereoselective Carbon–Carbon Bond-forming Reactions on Cyclopropane Rings Using 1-(Methoxycarbonyl)cyclopropylzinc Bromides
  作者：Daichi Sakuma、Kenta Yamada、Kazuya Sasazawa、Yoshinori Nishii

  DOI：10.1246/cl.150085

  日期：2015.6.5

  Highly stereoselective Reformatsky reaction and Pd-catalyzed arylation using 1-(alkoxycarbonyl)cyclopropylzinc bromide proceeded to give the trans-adduct as the major product in good to high yields with good to excellent stereoselectivities.

  高立体选择性的Reformatsky反应和钯催化的芳基化反应，使用1-(烷氧基羧酸基)环丙基溴化锌，得到的反式加成物作为主要产物，产率较好到很高，立体选择性较好到优秀。