(E)-N,N-Diethyl-2-methyl-3-phenylpent-2-enamide | 368425-65-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N,N-Diethyl-2-methyl-3-phenylpent-2-enamide
• 英文别名: (E)-N,N-diethyl-2-methyl-3-phenylpent-2-enamide
• CAS: 368425-65-4
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: NOUAQOVCKJVYTO-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  二碘甲烷 、 (E)-N,N-Diethyl-2-methyl-3-phenylpent-2-enamide 在 三氢化钐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(+/-)-(1S,2R)-N,N-diethyl-2-ethyl-2-phenyl-1-methylcyclopropanocarboxamide
  参考文献：
  名称：

  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.

  摘要：

  DOI：

  10.1002/1521-3773(20020603)41:11<1917::aid-anie1917>3.0.co;2-1
• 作为产物：
  描述：

  N,N-二乙基-2-氯丙酰胺 在 samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 (E)-N,N-Diethyl-2-methyl-3-phenylpent-2-enamide
  参考文献：
  名称：

  由α，β-环氧酰胺和二碘化total以全部或非常高的选择性合成芳族（E）或（Z）-α，β-不饱和酰胺。

  摘要：

  通过用二碘化treatment处理芳香族α，β-环氧酰胺，可以高度立体选择性地合成芳香族α，β-不饱和酰胺。起始化合物1和3易于通过衍生自α-氯酰胺的烯醇化物与羰基化合物在-78℃下反应来制备。提出了解释这种转化的机理。

  DOI：

  10.1021/jo0349577

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。
• Highly Stereoselective Halocyclopropanation of α,β-Unsaturated Amides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Elena G. Blanco、María A. Villa-García、Noemí Alvaredo、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1002/adsc.200900331

  日期：2009.9

  A convenient highly stereoselective synthesis of chloro- and bromocyclopropanamides from di- tri- or tetrasubstituted (E)- or (Z)-α,β-unsaturated amides with total or high stereoselectivity promoted by chromium dichloride or dibromide is described. The transformation of chlorocyclopropanamides into the corresponding ketones or amines is also reported. A mechanism to explain these transformations is

  从二-三-或四取代的（氯-和bromocyclopropanamides的一种方便的高度立体选择性合成ë） -或（Ž）-α，β -与由二氯化铬或二溴化物促进总或高立体选择性不饱和酰胺进行说明。还报道了氯环丙烷酰胺向相应的酮或胺的转化。提出了一种解释这些转换的机制。
• Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide
  作者：José M. Concellón、Juan A. Pérez-Andrés、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f

  日期：2001.7.16

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.
• 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.
• Synthesis of Aromatic (<i>E</i>)- or (<i>Z</i>)-α,β-Unsaturated Amides with Total or Very High Selectivity from α,β-Epoxyamides and Samarium Diiodide
  作者：José M. Concellón、Eva Bardales

  DOI：10.1021/jo0349577

  日期：2003.11.1

  stereoselective synthesis of aromatic alpha,beta-unsaturated amides was achieved by treatment of aromatic alpha,beta-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from alpha-chloroamides with carbonyl compounds at -78 degrees C. A mechanism to explain this transformation is proposed.

  通过用二碘化treatment处理芳香族α，β-环氧酰胺，可以高度立体选择性地合成芳香族α，β-不饱和酰胺。起始化合物1和3易于通过衍生自α-氯酰胺的烯醇化物与羰基化合物在-78℃下反应来制备。提出了解释这种转化的机理。