3,3-Bis(dimethylamino)-1-phenyl-prop-1-in | 19176-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-Bis(dimethylamino)-1-phenyl-prop-1-in
• 英文别名: N.N.N'.N'-Tetramethyl-3-phenyl-propin-(2)-ylidendiamin；3,3-Bis-dimethylamino-1-phenyl-propin-(1)；(1-Dimethylamino-3-phenyl-prop-2-ynyl)-dimethyl-amine；1-N,1-N,1-N',1-N'-tetramethyl-3-phenylprop-2-yne-1,1-diamine
• CAS: 19176-74-0
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: FYBPVCHWYZVTSU-UHFFFAOYSA-N

物化性质

• 沸点：
  262.6±30.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3,3-Bis(dimethylamino)-1-phenyl-prop-1-in 在 叠氮基三甲基硅烷 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到Dimethyl-[5-phenyl-[1,2,3]triazol-(4Z)-ylidenemethyl]-amine
  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
• 作为产物：
  描述：

  Bredereck 试剂 、 苯乙炔 生成 3,3-Bis(dimethylamino)-1-phenyl-prop-1-in
  参考文献：
  名称：

  Bredereck,H. et al., Chemische Berichte, 1970, vol. 103, p. 210 - 221

  摘要：

  DOI：

文献信息

• Synthesis of Polyfunctional Unsaturated Amines by the Addition of Functionalized Organomagnesium Reagents to Unsaturated Imminium Ions
  作者：Paul Knochel、Nina Gommermann、Christopher Koradin

  DOI：10.1055/s-2002-34369

  日期：——

  at low temperature produces imminium salts, which react in the presence of N-methylpyrrolidinone (NMP) with functionalized arylmagnesium compounds, providing polyfunctional propargylic and allylic amines in satisfactory yields.

  炔丙基胺和烯丙基胺与三氟甲磺酸酐在低温下反应生成亚胺盐，该亚胺盐在 N-甲基吡咯烷酮 (NMP) 存在下与官能化芳基镁化合物反应，以令人满意的收率提供多官能炔丙基胺和烯丙基胺。
• The synthesis and chemistry of 3-pheynl-2-propynylmultiamines
  作者：H. Weingarten

  DOI：10.1016/s0040-4020(01)82548-5

  日期：1968.1
• 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.
• Bredereck,H. et al., Chemische Berichte, 1970, vol. 103, p. 210 - 221
  作者：Bredereck,H. et al.

  DOI：——

  日期：——