反式-2-己烯醛N,N-二甲基腙 | 66064-52-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 反式-2-己烯醛N,N-二甲基腙
• 英文名称: trans-2-hexenal N,N-dimethylhydrazone
• 英文别名: Hex-2-enal-N,N-dimethyl-hydrazon；N-[(E)-[(E)-hex-2-enylidene]amino]-N-methylmethanamine
• CAS: 66064-52-6
• 化学式: C₈H₁₆N₂
• 分子量: 140.228
• InChiKey: KSIQSTNLRCGAPJ-BLHCBFLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-2-己烯醛N,N-二甲基腙 以76%的产率得到
  参考文献：
  名称：

  ZIMMERMANN B.; LERCHE H.; SEVERIN T., CHEM. BER., 119,(1986) N 9, 2848-2858

  摘要：

  DOI：
• 作为产物：
  描述：

  偏二甲肼 以64%的产率得到
  参考文献：
  名称：

  DUHAMEL L.; VALNOT J.-Y., C. R. ACAD. SCI., 1978, C286, NO 1

  摘要：

  DOI：

文献信息

• Improvements in the Hetero Diels-Alder Reactions of 1-Dimethylamino-1-azadienes in the Presence of an Electrophilic Scavenger Resin
  作者：Eva Pascual-Alfonso、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1055/s-2000-6501

  日期：2000.2

  Reactions between 1-dimethylamino-1-azadienes and several quinones in the presence of a chloroformyl polystyrene resin proceeded with up to 2.5-fold increase in the isolated yields of the hetero Diels-Alder products, owing to efficient scavenging of dimethylamine liberated from the primary cycloadducts.

  1-二甲氨基-1-氮杂二烯和几种醌在氯甲酰聚苯乙烯树脂存在下进行反应，由于有效清除了从伯胺中释放出的二甲胺，杂狄尔斯-阿尔德产物的分离收率增加了 2.5 倍。环加合物。
• Reaction of Tantalum-Alkyne Complexes with Hydrazones. Stereoselective Synthesis of (E)-Allylic Hydrazines.
  作者：Kazuhiko Takai、Seiji Miwatashi、Yasutaka Kataoka、Kiitiro Utimoto

  DOI：10.1246/cl.1992.99

  日期：——

  Treatment of tantalum-alkyne complexes with dimethylhydrazones by the assistance of Me 3 Al in a mixed solvent of DME, benzene, and THF at 45°C for 16 h gives (E)-allylic hydrazines stereoselectively

  在二甲醚、苯和四氢呋喃的混合溶剂中，在 Me 3 Al 的帮助下，在 45°C 下用二甲基腙处理钽-炔配合物 16 小时，立体选择性地得到 (E)-烯丙基肼
• Improved Efficient Conversion of Aldehydes to Nitriles <i>via</i> Their N, N-Dimethyl Hydrazones
  作者：Ahmed Kamal、M. Arifuddin、N. VenugopalRao

  DOI：10.1080/00397919808004513

  日期：1998.12

  Aldehyde N,N-dimethylhydrazones undergoes facile oxidative cleavage to nitriles on reaction with DIMS and K2CO3 in quantitative yields. Nitriles can also be easily obtained in high yields in a 'one-pot' process starting from the corresponding aldehydes.
• 1,2-Reduction of α,β-unsaturated hydrazones using dimethylamine–borane/p-toluenesulfonic acid: an easy route to allyl hydrazines
  作者：Maria E Casarini、Franco Ghelfi、Emanuela Libertini、Ugo M Pagnoni、Andrew F Parsons

  DOI：10.1016/s0040-4020(02)00914-6

  日期：2002.9

  alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin
  作者：Rita Cagnoli、Franco Ghelfi、Ugo M Pagnoni、Andrew F Parsons、Luisa Schenetti

  DOI：10.1016/j.tet.2003.10.046

  日期：2003.12

  The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.