N',N'-dimethyl-formamidin-hydrochlorid | 20353-92-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N',N'-dimethyl-formamidin-hydrochlorid
• 英文别名: N,N-dimethylformamidine hydrochloride；N,N-Dimethylformamidinium-chlorid；N,N-dimethyl-formamidine; hydrochloride；N,N-Dimethyl-formamidin; Hydrochlorid；dimethylaminomethylene ammonium chloride；1,1-Dimethyl-formamidin-hydrochlorid；Aminomethylidene(dimethyl)azanium;chloride
• CAS: 20353-92-8
• 化学式: C₃H₈N₂*ClH
• 分子量: 108.571
• InChiKey: CHJQVUHGYWACSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 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：
  27.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N',N'-dimethyl-formamidin-hydrochlorid 、 三氯乙腈 在 1,3-diazabicyclo[5.4.0]-undec-7-ene 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以52%的产率得到4-Dimethylamino-2-trichloromethyl-1,3-diazabutadiene
  参考文献：
  名称：

  1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

  摘要：

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

  DOI：

  10.1021/jo952106w
• 作为产物：
  描述：

  1-[4-[(E)-dimethylaminomethylideneamino]-2,5-dioxo-1,3-diphenylimidazolidin-4-yl]-3,3-dimethyl-1-phenylurea 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 非草隆 、 1,3-二苯基仲班酸 、 N',N'-dimethyl-formamidin-hydrochlorid
  参考文献：
  名称：

  Zur Reaktion zwischen双（二甲氨基）乙腈和苯基异氰酸酯。福尔蒂米特·米特隆

  摘要：

  双（二甲氨基）乙腈与苯异氰酸酯的反应

  DOI：

  10.1002/hlca.19800630723

文献信息

• Kantlehner, Willi; Haug, Erwin; Isak, Heinz, Chemische Berichte, 1982, vol. 115, # 5, p. 1721 - 1732
  作者：Kantlehner, Willi、Haug, Erwin、Isak, Heinz、Schulz, Wolfgang、Hippich, Silvin、et al.

  DOI：——

  日期：——
• SECKINGER K., HELV. CHIM. ACTA, 1980, 63, NO 7, 1958-1959
  作者：SECKINGER K.

  DOI：——

  日期：——
• DANISHEFSKY, S.;CHACKALAMANNIL, S.;SILVESTRI, M., J. ORG. CHEM., 1983, 48, N 20, 3615-3616
  作者：DANISHEFSKY, S.、CHACKALAMANNIL, S.、SILVESTRI, M.

  DOI：——

  日期：——
• 1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹
  作者：Angel Guzmán、Moisés Romero、Francisco X. Talamás、Rene Villena、Robert Greenhouse、Joseph M. Muchowski

  DOI：10.1021/jo952106w

  日期：1996.1.1

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.
• Zur Reaktion zwischen Bis (dimethylamino)acetonitril und Phenylisocyanat. Vorläufige Mitteilung
  作者：Karl Seckinger

  DOI：10.1002/hlca.19800630723

  日期：1980.10.29

  On the Reaction of Bis(dimethylamino)acetonitrile with Phenylisocyanate

  双（二甲氨基）乙腈与苯异氰酸酯的反应