1-(2-phenyl-cyclopropanecarbonyl)-pyrrolidine | 86597-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(2-phenyl-cyclopropanecarbonyl)-pyrrolidine
• 英文别名: (2-phenylcyclopropyl)-pyrrolidin-1-ylmethanone
• CAS: 86597-69-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: YDVBLKDIWQKVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二苯基乙炔 、 1-(2-phenyl-cyclopropanecarbonyl)-pyrrolidine 在 bis(1,5-cyclooctadiene)nickel (0) 、 三甲基铝 、 三苯基膦 、 Diphenylphosphine oxide 作用下， 以 正己烷 、 均三甲苯 为溶剂， 反应 24.0h， 以80%的产率得到
  参考文献：
  名称：

  Ni–Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne

  摘要：

  A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an, efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.

  DOI：

  10.1021/jacs.7b09947
• 作为产物：
  描述：

  2-苯基环丙烷羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-(2-phenyl-cyclopropanecarbonyl)-pyrrolidine
  参考文献：
  名称：

  Ni–Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne

  摘要：

  A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an, efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.

  DOI：

  10.1021/jacs.7b09947

文献信息

• Nickel enolates in the Ni(CO)4 -induced carbonylation of gem-dibromocyclopropanes with silylamine or silylsulfide
  作者：Toshikazu Hirao、Shinichiro Nagata、Yoshihiro Yamana、Toshio Agawa

  DOI：10.1016/s0040-4039(01)80853-4

  日期：——

  were successfully used in the Ni(CO)4 -induced carbonylation reactions of gem-dibromocyclopropanes. The nickel carbenoid and enolate complexes are considered to be involved as key intermediates. Protonation afforded the cyclopropanecarboxylic acid derivatives. The presence of an electrophile achieved another stereoselective carbon-carbon bond formation via the nickel enolate intermediate.

  甲硅烷基化合物（N，N-二烷基三甲基甲硅烷基胺，1-（三甲基甲硅烷基）-咪唑和苯硫基三甲基硅烷）已成功用于Ni（CO）4诱导的宝石-二溴环丙烷的羰基化反应。类胡萝卜素和烯醇化镍配合物被认为是关键中间体。质子化得到环丙烷羧酸衍生物。亲电子试剂的存在通过烯醇镍中间体实现了另一种立体选择性碳-碳键的形成。
• Tetracarbonyl nickel induced reaction of gem-dibromocyclopropanes with alcohols or amines.
  作者：Toshikazu Hirao、Yoshiyuki Harano、Yoshihiro Yamana、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1016/s0040-4039(00)81628-7

  日期：1983.1
• HIRAO, TOSHIKAZU;HARANO, YOSHIYUKI;YAMANA, YOSHIHIRO;OHSHIRO, YOSHIKI;AGA+, TETRAHEDRON LETT., 1983, 24, N 12, 1255-1258
  作者：HIRAO, TOSHIKAZU、HARANO, YOSHIYUKI、YAMANA, YOSHIHIRO、OHSHIRO, YOSHIKI、AGA+

  DOI：——

  日期：——
• HIRAO TOSHIKAZU; HARANO YOSHIYUKI; YAMANA YOSHIHIRO; HAMADA YUJI; NAGATA +, BULL. CHEM. SOC. JAP., 59,(1986) N 5, 1341-1347
  作者：HIRAO TOSHIKAZU、 HARANO YOSHIYUKI、 YAMANA YOSHIHIRO、 HAMADA YUJI、 NAGATA +

  DOI：——

  日期：——
• Asymmetric Cobalt-Catalyzed Cyclopropanation With Succinimidyl Diazoacetate
  申请人：Zhang X. Peter

  公开号：US20120077959A1

  公开（公告）日：2012-03-29

  Cobalt(II) complexes of the D 2 -symmetric chiral porphyrins are effective catalysts for asymmetric cyclopropanation reactions with succinimidyl diazoacetate. The Co-catalyzed reaction is suitable for various olefins, providing the corresponding cyclopropane succinimidyl esters in high yields and excellent diastereo- and enantio-selectivity. The resulting enantioenriched cyclopropane succinimidyl esters can serve as convenient synthons for the general synthesis of optically active cyclopropyl carboxamides through mild reactions with a wide range of amine derivatives, including unprotected peptides and amino sugars