methyl 2-chloro-2-(1-methoxycyclopropyl)acetate | 82979-36-0

• 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 2-chloro-2-(1-methoxycyclopropyl)acetate
• CAS: 82979-36-0
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: UISXLOUCSZWNAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-chloro-2-(1-methoxycyclopropyl)acetate 在 三乙胺 、 lithium iodide 作用下， 以 乙腈 为溶剂， 反应 168.0h， 以67%的产率得到Methyl 2-methoxycyclobutenecarboxylate
  参考文献：
  名称：

  Cyclopropyl building blocks for organic synthesis. Part 22. Facile synthesis of stable analogs of 2-oxocyclobutanecarboxylates: 2-[(diphenylmethylene)amino]cyclobutenecarboxylates, derivatives and reactions

  摘要：

  An efficient two-step synthesis of 2-[(diphenylmethylene)amino]cyclobutenecarboxylate (4a) and some analogous derivatives from 2-chloro-2-cyclopropylideneacetates 2, 17, 22, and 25 and nonenolizable ketimines, especially diphenylmethyleneamine (DPMA-H), is described. A likely mechanism for the formation of 4a from the primary Michael adduct 3 of DPMA-H to 2 and its substituted analogues is presented. The unique neighboring group effect of the DPMA moiety to allow formation of an azaspiropentane intermediate and its regioselective rearrangement to cyclobutenamine derivatives is discussed and further exemplified by an extremely facile SET alpha-chlorination. Compound 4a and derivatives undergo a thermal ring-opening reaction to the corresponding butadienes with subsequent formation of 1,3-disubstituted 3,4-dihydroisoquinolines 39. Further transformations of 4a and some derivatives include transesterification, hydrolysis to methyl 2-oxocyclobutanecarboxylates, and addition of N-phenyltriazolinedione.

  DOI：

  10.1021/jo00075a047
• 作为产物：
  描述：

  trimethyl 2-chloro-2-cyclopropylidenorthoacetate 在 氢气 作用下， 以 水 为溶剂， 生成 methyl 2-chloro-2-(1-methoxycyclopropyl)acetate
  参考文献：
  名称：

  Liese, Thomas; Splettstoesser, Gisela; Meijere, Armin de, Angewandte Chemie, 1982, vol. 94, # 10, p. 799

  摘要：

  DOI：

文献信息

• LIESE, T.;SPLETTSTOESSER, G.;MEIJERE, A., ANGEW. CHEM., 1982, 94, N 10, 799
  作者：LIESE, T.、SPLETTSTOESSER, G.、MEIJERE, A.

  DOI：——

  日期：——