3,3-Bis(dimethylamino)prop-1-in | 187390-23-4

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: 3,3-Bis(dimethylamino)prop-1-in
• 英文别名: 1-N,1-N,1-N',1-N'-tetramethylprop-2-yne-1,1-diamine
• CAS: 187390-23-4
• 化学式: C₇H₁₄N₂
• 分子量: 126.202
• InChiKey: URJJZELCCJCVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  六甲基氯胍 、 3,3-Bis(dimethylamino)prop-1-in 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 以48%的产率得到1,1,1,4,4-Pentakis(dimethylamino)but-2-in
  参考文献：
  名称：

  Kantlehner, Willi; Stieglitz, Ruediger; Hauber, Michael, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 3, p. 256 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  乙炔钠 、 (二甲氨基亚甲基)二甲基氯化铵 以 四氢呋喃 为溶剂， 反应 20.0h， 以5.8%的产率得到1,1,4,4-Tetrakis(dimethylamino)-but-2-in
  参考文献：
  名称：

  Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

  摘要：

  Tert-butylaminalester 5 reacts with terminal alkynes to give aminals of substituted propiolaldehydes 3c,d. The aminal 3a is accessible from N,N,N,N'-tetramethylformamidinium chloride (7b) and sodium acetylide. The aminals 3b,c can also be prepared from bis(dimethylamino)acetonitrile 8 and terminal alkynes in the presence of sodium hydride. The nitrile 8 is also useful for the preparation of the bis-aminal of acetylenedialdehyde 6. The aminal 3e can be transaminated by heating with secondary amines to give the aminals 3f-i. The aminals 3a-i react with strong CH2-acidic compounds (pK(a) between 9 and 14) to give the 1-dialkylamino-1,3-butadienes 10. The isomeric 1-dialkylamino-butadienes 18 can be obtained from the condensation of the CH-acidic cinnamic acid derivatives 19 with dimethylformamidedimethylacetal. CH and NH-acidic compounds as cyanacetamide react with the aminals 3c,e exclusively with the acidic methylene group to produce the enamines 10h,t. The acylformamidine 21 can be obtained from 10t and tert-butylaminalester 5. The pyridone 22 is accessible from the condensation product 10h by thermal cyclization. The pyrido[2,3-d]pyrimidine 26 is formed in the reaction of the 6-amino-uracile 23 with the aminal 3a. In an unexpected reaction the 1,2-bis(cyano-dialkylaminomethylene)-cyclobutanes 28a-d result from the action of trimethylsilylcyanide on the aminals 3e-h. The corresponding reaction with trimethylsilylisothiocyanate affords the vinylogous amidinium thiocyanates 34a,b. In the reaction of trimethylsilylazide and the aminals 3 are produced the 4-(dialkylaminomethylene)-4H-1,2,3-triazoles 38.

  DOI：

  10.1002/prac.19973390130

文献信息

• Procédé de fabrication du chlorure de l'acrylate de 1,3-bis (dimethylbenzylammonium) isopropyle seul ou en mélange avec d'autres monomères et (co)polymères correspondants
  申请人：Atofina

  公开号：EP1253137A1

  公开（公告）日：2002-10-30

  On prépare un composé de formule (I) seul ou en combinaison avec au moins un monomère de formule (II) : on introduit l'agent quaternisant chlorure de benzyle dans une solution, dans un solvant choisi parmi les composés des formules (I) et (II) et leurs mélanges, du composé de formule (III) à une température de 35 à 60°C, puis on ajoute de l'eau et on laisse se dérouler la réaction jusqu'à conversion complète ou sensiblement complète du composé (III), on sépare une solution aqueuse de composé recherché (I) le cas échéant avec au moins un composé (II) si on a utilisé celui-ci ou ceux-ci comme solvant, et on élimine l'eau le cas échéant.         R = -CH3 ou -CH2C6H5.

  单独或与至少一种式（II）单体结合制备式（I）化合物：在 35 至 60°C 的温度下，在从式（I）和（II）化合物及其混合物中选择的溶剂中，将季铵化剂苄氯引入式（III）化合物的溶液中、然后加入水，使反应继续进行，直至化合物 (III) 转化完全或基本完全，分离出所需化合物 (I) 的水溶液，如果至少有一种化合物 (II) 用作溶剂，则酌情与之分离，并酌情除去水。 R = -CH3 或 -CH2C6H5。
• DISPERSIONS AQUEUSES SALINES DE COPOLYMERES HYDROSOLUBLES A BASE DE MONOMERES CATIONIQUES, LEUR PROCEDE DE FABRICATION ET LEURS APPLICATIONS
  申请人：Atofina

  公开号：EP1252206B1

  公开（公告）日：2004-01-07
• DISPERSIONS AQUEUSES SALINES DE (CO)POLYMERES HYDROSOLUBLES A BASE DE MONOMERES CATIONIQUES, LEUR PROCEDE DE FABRICATION ET LEURS APPLICATIONS
  申请人：Atofina

  公开号：EP1252208B1

  公开（公告）日：2004-01-07
• Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen
  作者：Michael Kiesel、Erwin Haug、Willi Kantlehner

  DOI：10.1002/prac.19973390130

  日期：——

  Tert-butylaminalester 5 reacts with terminal alkynes to give aminals of substituted propiolaldehydes 3c,d. The aminal 3a is accessible from N,N,N,N'-tetramethylformamidinium chloride (7b) and sodium acetylide. The aminals 3b,c can also be prepared from bis(dimethylamino)acetonitrile 8 and terminal alkynes in the presence of sodium hydride. The nitrile 8 is also useful for the preparation of the bis-aminal of acetylenedialdehyde 6. The aminal 3e can be transaminated by heating with secondary amines to give the aminals 3f-i. The aminals 3a-i react with strong CH2-acidic compounds (pK(a) between 9 and 14) to give the 1-dialkylamino-1,3-butadienes 10. The isomeric 1-dialkylamino-butadienes 18 can be obtained from the condensation of the CH-acidic cinnamic acid derivatives 19 with dimethylformamidedimethylacetal. CH and NH-acidic compounds as cyanacetamide react with the aminals 3c,e exclusively with the acidic methylene group to produce the enamines 10h,t. The acylformamidine 21 can be obtained from 10t and tert-butylaminalester 5. The pyridone 22 is accessible from the condensation product 10h by thermal cyclization. The pyrido[2,3-d]pyrimidine 26 is formed in the reaction of the 6-amino-uracile 23 with the aminal 3a. In an unexpected reaction the 1,2-bis(cyano-dialkylaminomethylene)-cyclobutanes 28a-d result from the action of trimethylsilylcyanide on the aminals 3e-h. The corresponding reaction with trimethylsilylisothiocyanate affords the vinylogous amidinium thiocyanates 34a,b. In the reaction of trimethylsilylazide and the aminals 3 are produced the 4-(dialkylaminomethylene)-4H-1,2,3-triazoles 38.
• Kantlehner, Willi; Stieglitz, Ruediger; Hauber, Michael, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 3, p. 256 - 268
  作者：Kantlehner, Willi、Stieglitz, Ruediger、Hauber, Michael、Haug, Erwin、Regele, Claudia

  DOI：——

  日期：——