(E)-N,N-Diethyl-2-methyldec-2-enamide | 368425-53-0

• 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: (E)-N,N-Diethyl-2-methyldec-2-enamide
• CAS: 368425-53-0
• 化学式: C₁₅H₂₉NO
• 分子量: 239.401
• InChiKey: CMBVDJVFCQHATN-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-methyldec-2-enamide 在 三氢化钐 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (+/-)-(1S,2S)-N,N-diethyl-2-heptyl-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
• 作为产物：
  描述：

  2,3-epoxy-N,N-diethyl-2-methyldecanamide 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (E)-N,N-Diethyl-2-methyldec-2-enamide
  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

• Stereoselective Olefination Reactions Promoted by Rieke Manganese
  作者：José Concellón、Humberto Rodríguez-Solla、Vicente del Amo、Pamela Díaz

  DOI：10.1055/s-0029-1216880

  日期：2009.8

  applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. manganese - elimination reactions - stereoselectivity - α,β-unsaturated esters - α,β-unsaturated amides - metalation

  提出了使用廉价的无毒金属锰进行立体选择性β-消除反应并促进醛的顺序烯化反应以获得α，β-不饱和酯和酰胺的优势的研究。使用活性锰（Mn *）作为金属化剂进行了各种消除反应，所有这些反应均具有完全的立体选择性和高收率的特征。锰的这种能力已被用于开发通过Mn *-直接合成（E）-α，β-不饱和酯或酰胺与（Z）-α，β-不饱和α-卤代酯和α-氯酰胺的新颖而直接的合成方法。介导的醛分别与二氯酯或酰胺和三卤代酯或三氯酰胺的顺序烯烃化方案。 锰-消除反应-立体选择性-α，β-不饱和酯-α，β-不饱和酰胺-金属化
• 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。
• Manganese-Promoted Regioselective Ring-Opening of 2,3-Epoxy Acid Derivatives: A New Route to α-Hydroxy Acid Derivatives
  作者：José M. Concellón、Pablo L. Bernad、Humberto Rodríguez-Solla、Pamela Díaz

  DOI：10.1002/adsc.200900257

  日期：2009.9

  amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.

  描述了一种简单而通用的方法，该方法涉及由活性锰促进的从容易获得的2，3-环氧酰胺或酯合成3-芳基-2-羟基酰胺或具有总区域选择性的酯。利用对映纯的环氧酰胺作为起始原料，也可获得对映纯的相应的3-芳基-2-羟基酰胺。显示了3-芳基-2-羟基羧酸衍生物的选定实例的一些合成应用。已经提出了一种机制来解释这种新颖的反应。
• Synthesis of Aliphatic (E)-α,β-Unsaturated Amides with High Diastereoselectivity fromα,β-Epoxyamides Promoted by SmI2/HMPA
  作者：José M. Concellón、Eva Bardales

  DOI：10.1002/ejoc.200300641

  日期：2004.4

  Synthesis of aliphatic (E)-α,β-unsaturated amides 2, in which the C=C bond is di- or trisubstituted, is achieved by using samarium diiodide and HMPA. The starting compounds 1 were easily prepared by the reaction of the corresponding lithium or potassium enolates of α-chloroamides with aldehydes. A mechanism to explain this process is proposed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  通过使用二碘化钐和 HMPA 合成脂肪族 (E)-α,β-不饱和酰胺 2，其中 C=C 键被二或三取代。起始化合物 1 很容易通过相应的 α-氯酰胺的烯醇锂或烯醇钾与醛反应来制备。提出了一种解释这一过程的机制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• 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。