1-环己烯甲醛二甲基腙 | 66064-59-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-环己烯甲醛二甲基腙
• 英文名称: 1-cyclohexen-1-carboxaldehyde N,N-dimethylhydrazone
• 英文别名: N'-(cyclohex-1-enylmethylene)-N,N-dimethylhydrazone；1-Cyclohexen-1-carbaldehyd-dimethylhydrazon；1-cyclohexenecarboxaldehyde dimethylhydrazone；N-[(E)-cyclohexen-1-ylmethylideneamino]-N-methylmethanamine
• CAS: 66064-59-3
• 化学式: C₉H₁₆N₂
• 分子量: 152.239
• InChiKey: KFEVYRZHPBJFSI-CSKARUKUSA-N

物化性质

• 沸点：
  80 °C(Press: 0.7 Torr)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-环己烯甲醛二甲基腙 以83%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：
• 作为产物：
  描述：

  偏二甲肼 以84%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

• Aza-enamines XI.¹ Vinylogous Aza-enamines as Neutral d³-Nucleophiles: Aminomethylations of N,N-Dimethylhydrazones of α,β-Unsaturated Aldehydes
  作者：Rainer Brehme、Christoph Schalley、Matthias Grabowski、Karol Nowosinski、Dieter Lentz

  DOI：10.1055/s-0030-1258194

  日期：2010.10

  moisture-free dimethylformamide to yield singly, doubly, and even triply aminomethylated products. They can be easily separated and characterized as crystalline hydrochlorides. The reaction takes place at the ω-position of the π-system. This is a consequence of the conjugative interaction of the electron-donating aminohydrazone group with the double bond system in analogy to the enamines. The formation of

  Ñ，Ñ的-Dimethylhydrazones propenal-和2-甲基丙烯醛和它们的衍生物和同系物（插烯氮杂烯胺）被允许与反应Ñ，Ñ -dimethylformiminium酰氯在无水分二甲基甲酰胺，得到单，双，和甚至三重氨基甲基化产品。它们可以很容易地分离并表征为盐酸盐。该反应在π系统的ω位置发生。这是供电子的氨基hydr基团与双键系统类似烯胺类的共轭相互作用的结果。从不饱和醛dialkylhydrazones的形成从而使原电d的极性转换³-构建块成亲核试剂。根据反应条件，并通过晶体结构和2D NMR实验证实，可以控制取代度：对于2-甲基丙烯醛衍生物，最多可获得三取代产物。盐酸盐可以很容易地去质子化，得到游离的氨基hydr碱。在酸性条件下可以将氨基azo还原成相应的氨基醛。 -亲电子取代-亲核加成-氨基乙醛-物质 对于氮杂烯胺的第十部分，请参见参考资料。4d。
• [4 + 2]-Cycloadditionen von ?,?-unges�ttigten Hydrazonen. Teil 1. Pyridin-2,3-dicarboximide aus 1-(Dimethylamino)-1,4-dihydropyridin-Derivaten
  作者：Adrian Waldner

  DOI：10.1002/hlca.19880710222

  日期：1988.3.16

  [4 + 2] Cycloadditions of α,β-Unsaturated Hydrazones to Pyridine-2,3-dicarboximides via 1-(Dimethylamino)-1,4-dihydropyridine Derivatives

  [4 + 2]通过1-（二甲氨基）-1,4-二氢吡啶衍生物将α，β-不饱和Hy与吡啶-2,3-二羧酸二甲酰亚胺成环加成反应
• [4+2]-Cycloadditionen von ?,?-unges�ttigten Hydrazonen. Teil 2. Pyridin-2,3-dicarboximide aus 1,4-Dihydropyridin-Derivaten
  作者：Adrian Waldner

  DOI：10.1002/hlca.19880710223

  日期：1988.3.16

  [4+2] Cycloaddition of α,β-Unsaturated Hydrazones to Pyridine-2,3-dicarboximides via 1,4-Dihydropyridine Derivatives

  [4 + 2]通过1，4-二氢吡啶衍生物将α，β-不饱和dra与2,3-二吡啶嘧啶吡啶进行环加成反应
• 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.
• Studies on quinones. Part 32. Regioselective synthesis of benz[b]phenantridines related to phenantroviridone
  作者：Jaime A. Valderrama、M.Florencia González、Claudio Valderrama

  DOI：10.1016/s0040-4020(99)00278-1

  日期：1999.5

  The Diels-Alder reaction of juglone (4) and bromojuglone 18 with 1-cyclohesenecarbosaldehyde dimethylhydrazone (3) is described. Through these cycloaddition reactions 8-hydroxy-1,2,3,4-tetrahydrobenz[b]phenantridin-7,12-dione (5) was obtained in 55 and 78% yield, respectively. Oxidation of 5 to 8-hydroxybenz[b]phenantridin-7,12-dione (6) and 8-hydroxy-1,2,3,4-tetrahydrobenz[b]phenantridin-1,7,12-trione (15) is also reported. (C) 1999 Elsevier Science Ltd. All rights reserved.