3-amino-4,4-dimethyl-1-pentyne | 5689-93-0

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3-amino-4,4-dimethyl-1-pentyne
• 英文别名: 4,4-Dimethylpent-1-yn-3-amine
• CAS: 5689-93-0
• 化学式: C₇H₁₃N
• mdl: MFCD19205298
• 分子量: 111.187
• InChiKey: PMWAAXIXEBSFCD-UHFFFAOYSA-N

物化性质

• 沸点：
  142.0±13.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-amino-4,4-dimethyl-1-pentyne 在 dodecacarbonyltetrarhodium(0) sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 50.0~100.0 ℃ 、3.04 MPa 条件下， 反应 4.0h， 生成 (Z)-4,4-dimethyl-2-[(dimethyl-biphenylsilyl)methylene]-3-(p-tosylamino)pentanal
  参考文献：
  名称：

  Silylation–desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams

  摘要：

  Propargyl functionalised beta-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of alpha, beta-unsaturated aldehydes through a two-step sequence of silylformylation -desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) alpha-silylmethylene-beta-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the b-lactam was observed when dialkyl propargyl amides were employed. The obtained b-lactams were easily transformed into the corresponding methylaryl-b-lactams by fluoride induced aryl migration -desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable b-lactam (E)-isomer. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.04.064
• 作为产物：
  描述：

  1-溴-4,4-二甲基-1,2-戊二烯 在 lithium amide 作用下， 以 氨 为溶剂， 反应 1.0h， 以93%的产率得到3-amino-4,4-dimethyl-1-pentyne
  参考文献：
  名称：

  Geri, Roberto; Polizzi, Carmela; Lardicci, Luciano, Gazzetta Chimica Italiana, 1994, vol. 124, # 6, p. 241 - 248

  摘要：

  DOI：

文献信息

• Kirmse,W.; Urbach,H., Chemische Berichte, 1972, vol. 105, p. 840 - 849
  作者：Kirmse,W.、Urbach,H.

  DOI：——

  日期：——
• Geri Roberto, Polizzi Carmela, Lardicci Luciano, Caporusso Anna Maria, Gazz. chim. ital, 124 (1994) N 6, S 241-248
  作者：Geri Roberto, Polizzi Carmela, Lardicci Luciano, Caporusso Anna Maria

  DOI：——

  日期：——