N-chloromethyl-N-methylformamide | 78357-38-7

• 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: N-chloromethyl-N-methylformamide
• 英文别名: N-methyl-N-chloromethylformamide；N-(Chlormethyl)-N-methylformamid；Formamide, N-(chloromethyl)-N-methyl-；N-(chloromethyl)-N-methylformamide
• CAS: 78357-38-7
• 化学式: C₃H₆ClNO
• 分子量: 107.54
• InChiKey: SFOPHQUYNPBUPF-UHFFFAOYSA-N

物化性质

• 沸点：
  56 °C(Press: 0.1 Torr)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-溴-2-丁烯 、 N-chloromethyl-N-methylformamide 在 锌 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到N-methyl-N-(2-methylbut-3-enyl)formamide
  参考文献：
  名称：

  Courtois, G.; Mesnard, D.; Mahoungou, J. R., Bulletin de la Societe Chimique de France, 1986, # 3, p. 449 - 453

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基甲酰胺 以73%的产率得到
  参考文献：
  名称：

  BOHME, H.;RAUDE, E., CHEM. BER., 1981, 114, N 10, 3421-3429

  摘要：

  DOI：

文献信息

• A new synthetic route to 2-alkyl-4-aryl-1(2H)-isoquinolones and 2-alkyl-4-aryl-1,2,3,4-tetrahydroisoquinolines
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Patrice Woisel

  DOI：10.1016/0040-4020(96)00092-0

  日期：1996.3

  4-Aryl and heteroaryl-1(2H)-isoquinolones have been prepared by base promoted cyclization of phosphorylated o-aroyl and heteroaroyl benzamides. Subsequent reduction of the carbonyl and styryl functions of the annulated products has given rise to 4-aryl-1,2,3,4-tetrahydroisoquinolines.

  已经通过磷酸化的邻芳基和杂芳基苯甲酰胺的碱促进的环化反应制备了4-芳基和杂芳基-1（2 H）-异喹诺酮。环化产物的羰基和苯乙烯基官能团的随后还原产生了4-芳基-1,2,3,4-四氢异喹啉。
• Synthesis of 2-substitutedO,O-bis(trimethylsilyl) alkylphosphonites with aryl and heterocyclic fragments and their amino or amido derivatives
  作者：Andrey A. Prishchenko、Mikhail V. Livantsov、Olga P. Novikova、Ludmila I. Livantsova、Valery S. Petrosyan

  DOI：10.1002/hc.20431

  日期：2008.5

  Free-radical addition of bis(trimethyl-siloxy)phosphine to various functionalized alkenes with aryl and heterocyclic fragments is proposed as a convenient procedure for the synthesis of new 2-substituted alkylphosphonites of corresponding structures. Also the new functionalized derivatives of these phosphonites, including various amino and amido groups as well as certain properties of these compounds

  双（三甲基-甲硅烷氧基）膦自由基加成到具有芳基和杂环片段的各种官能化烯烃被提议作为合成相应结构的新 2-取代烷基亚膦酸酯的便捷方法。还介绍了这些亚膦酸酯的新功能化衍生物，包括各种氨基和酰胺基以及这些化合物的某些特性。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:345–351, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20431
• Synthesis of new functionalized aminomethylphosphonites and their derivatives
  作者：Andrey A. Prishchenko、Mikhail V. Livantsov、Olga P. Novikova、Ludmila I. Livantsova、Valery S. Petrosyan

  DOI：10.1002/hc.20620

  日期：——

  aminomethylation of the several esters of hypophosphorous acid using chloro-, alkoxy-, and amino-substituted methylamines of various structure is proposed as convenient method for the synthesis of new functionalized aminomethylphosphonites and bis(aminomethyl)phosphinates. Also O,O-diethyl(pivaloyl)phosphonite is successfully applied in the aminomethylation as a synthetic analog of unstable diethoxyphosphine.

  提出了使用各种结构的氯代、烷氧基和氨基取代的甲胺对几种次磷酸酯进行氨基甲基化，作为合成新型功能化氨基甲基亚膦酸酯和双（氨基甲基）次膦酸酯的简便方法。O,O-二乙基（新戊酰基）亚膦酸酯也作为不稳定二乙氧基膦的合成类似物成功地应用于氨甲基化。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:361–367, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20620
• Alkenyl copper reagents—18
  作者：A. Alexakis、A. Commerčon、C. Coulentianos、J.F. Normant

  DOI：10.1016/s0040-4020(01)91100-7

  日期：1984.1

  Lithium diorganocuprates add across the triple bond of substituted and non-substituted acetylenic acetals and ketals to give dialkenylcuprates, which can be decomposed into alkoxyallenes or may be trapped with a variety of electrophiles, such as alkyl, alkenyl, alkynyl and aryl halides. They may also undergo conjugate addition to α-βunsaturated esters and ketones. The method is used for the synthesis

  二有机辛酸锂跨取代的和未取代的乙缩醛和缩酮的三键加成，得到二烯基铜酸酯，它们可以分解成烷氧基丙二烯或被多种亲电试剂捕获，例如烷基，烯基，炔基和芳基卤化物。它们也可以进行共轭加成到α-β不饱和酯和酮上。该方法用于合成（±）-甘露酮，纯香叶醛和（E，Z）2,4-二烯醛。
• Total Synthesis of Aplyronine C
  作者：Ian Paterson、Sarah J. Fink、Lydia Y. W. Lee、Stephen J. Atkinson、Simon B. Blakey

  DOI：10.1021/ol401327r

  日期：2013.6.21

  highly stereocontrolled total synthesis of the cytotoxic marine macrolide aplyronine C is described. The route exploits aldol methodology to install the requisite stereochemistry and features a crucial boron-mediated aldol coupling of an N-vinylformamide-bearing methyl ketone with a macrocyclic aldehyde to introduce the full side chain. The synthesis of two novel C21–C34 side chain analogs is also

  描述了细胞毒性海洋大环内酯 aplyronine C 的高度立体控制的全合成。该路线利用羟醛方法来安装必要的立体化学，并具有关键的硼介导的带有N-乙烯基甲酰胺的甲基酮与大环醛的羟醛偶联，以引入完整的侧链。还报道了两种新型 C21-C34 侧链类似物的合成。