(+/-)-(1S,2R)-2-cyclohexyl-N,N-diethyl-1-methylcyclopropanocarboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(1S,2R)-2-cyclohexyl-N,N-diethyl-1-methylcyclopropanocarboxamide
• 英文别名: (1R,2S)-2-cyclohexyl-N,N-diethyl-1-methylcyclopropane-1-carboxamide
• 化学式: C₁₅H₂₇NO
• 分子量: 237.385
• InChiKey: ARZUDWXFOGTDQW-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-cyclohexyl-2,3-epoxy-N,N-diethyl-2-methylpropanamide 在 三氢化钐 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.5h， 生成 (+/-)-(1S,2R)-2-cyclohexyl-N,N-diethyl-1-methylcyclopropanocarboxamide
  参考文献：
  名称：

  Sequenced elimination–reduction and elimination–cyclopropanation reactions of 2,3-epoxyamides promoted by samarium diiodide. Synthesis of 2,3-dideuterioamides and cyclopropanamides

  摘要：

  An easy and general sequenced elimination/reduction or elimination/cyclopropanation process promoted by samarium diiodide or/and CH2I2/Sm provide an efficient method for synthesising 2,3-dideuterioamides 3 or cyclopropanamides 8, respectively. The transformations take place in high yields and with total or high selectivity from the easily available 2,3-epoxyamides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.051

文献信息

• Stereospecific Cyclopropanation of Highly Substituted C−C Double Bonds Promoted by CrCl₂. Stereoselective Synthesis of Cyclopropanecarboxamides and Cyclopropyl Ketones
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Méjica、Elena G. Blanco

  DOI：10.1021/ol070896d

  日期：2007.8.1

  (Z)-alpha,beta-enamides in which the C-C double bond is di-, tri-, or tetrasubstituted. In all cases the process is completely stereospecific and only a single diastereoisomer is obtained. In addition, cyclopropyl ketones were readily prepared by reaction of the cyclopropanecarboxamides (derived from morpholine) obtained with a range of organolithium compounds. A mechanism has been proposed to explain the cyclopropanation

  我们在这里描述了CrCl（2）促进的α，β-不饱和酰胺的环丙烷化。该反应可以在其中CC双键被二，三或四取代的（E）-或（Z）-α，β-烯酰胺上进行。在所有情况下，该过程都是完全立体定向的，并且仅获得单个非对映异构体。另外，通过使所获得的环丙烷甲酰胺（衍生自吗啉）与一定范围的有机锂化合物反应，可以容易地制备环丙基酮。已经提出了解释环丙烷化反应的机理。
• Sequential Elimination−Cyclopropanation Reactions Promoted by Samarium:  Highly Diastereoselective Synthesis of Cyclopropylamides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Ricardo Llavona

  DOI：10.1021/jo0262098

  日期：2003.2.1

  trans-Cyclopropanamides were obtained, in high yield, from 2-chloro-3-hydroxyamides by a sequenced elimination-cyclopropanation process promoted by Samarium/diiodomethane or Samarium diiodide and Samarium/diiodomethane.
• Complete Stereospecific Cyclopropanation of α,β-Unsaturated Amides Promoted by Sm/CH2I2 We acknowledge financial support from II Plan Regional de Investigación del Principado de Asturias (PB-EXP01-11) and Ministerio de Ciencia y Tecnología (BQU2001-3807). We thank Dr. Francisco J. González for valuable discussions and Robin Walker for revising the English manuscript. J.M.C. thanks Carmen Fernández-Flórez for her time. H.R.S. thanks Principado de Asturias for a predoctoral fellowship.
  作者：José M. Concellón、Humberto Rodríguez-Solla、Cecilia Gómez

  DOI：10.1002/1521-3773(20020603)41:11<1917::aid-anie1917>3.0.co;2-1

  日期：2002.6.3
• Sequenced elimination–reduction and elimination–cyclopropanation reactions of 2,3-epoxyamides promoted by samarium diiodide. Synthesis of 2,3-dideuterioamides and cyclopropanamides
  作者：José M. Concellón、Mónica Huerta、Eva Bardales

  DOI：10.1016/j.tet.2004.07.051

  日期：2004.10

  An easy and general sequenced elimination/reduction or elimination/cyclopropanation process promoted by samarium diiodide or/and CH2I2/Sm provide an efficient method for synthesising 2,3-dideuterioamides 3 or cyclopropanamides 8, respectively. The transformations take place in high yields and with total or high selectivity from the easily available 2,3-epoxyamides. (C) 2004 Elsevier Ltd. All rights reserved.