N-Methallyl-o-toluidine | 131001-34-8

• 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: N-Methallyl-o-toluidine
• 英文别名: 2-Methyl-N-(2-methylprop-2-en-1-yl)aniline；2-methyl-N-(2-methylprop-2-enyl)aniline
• CAS: 131001-34-8
• 化学式: C₁₁H₁₅N
• mdl: MFCD16470032
• 分子量: 161.247
• InChiKey: DNWKTYZXPRNOIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Methallyl-o-toluidine 在 η⁶-C6H6BPh3^-Rh(COD)⁺ sodium tetrahydroborate 、 一氧化碳 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 100.0 ℃ 、3.5 MPa 条件下， 反应 30.0h， 以45%的产率得到3-Methyl-1-o-tolyl-pyrrolidine
  参考文献：
  名称：

  Synthesis of pyrrolidines and pyrrolidinones by the rhodium complex catalyzed cyclization of unsaturated amines

  摘要：

  N-Allylic arylamines react with carbon monoxide, sodium borohydride, 2-propanol, and catalytic amounts of the zwitterionic complex eta-6-C6H6BPh3-Rh(COD)+ (1), to form pyrrolidines as the main products in most cases. Pyrrolidinones result from N-allylic alkylamines. An alternate route to the lactams from N-allylic alkylamines involves synthesis gas instead of CO/NaBH4, together with the dual catalytic system 1/[Ru(CO)3Cl2]2. Complementary to the N-allylic arylamine route to pyrrolidines with NaBH4 and 1 is the use of synthesis gas, 1, and 1,4-bis(diphenylphosphino)butane.

  DOI：

  10.1021/jo00038a019
• 作为产物：
  描述：

  甲基硝基苯 、 2-Methylallylmagnesium Chloride 在 palladium on activated charcoal lithium aluminium tetrahydride 作用下， 生成 N-Methallyl-o-toluidine 、 N-Methallyl-N-(o-tolyl)hydroxylamine
  参考文献：
  名称：

  Barboni, Luciano; Bartoli, Giuseppe; Marcantoni, Enrico, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2133 - 2138

  摘要：

  DOI：

文献信息

• BARBON, LUCIANO;BARTOLI, GIUSEPPE;MARCANTONI, ENRICO;PETRINI, MARINO;DALP+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2133-2138
  作者：BARBON, LUCIANO、BARTOLI, GIUSEPPE、MARCANTONI, ENRICO、PETRINI, MARINO、DALP+

  DOI：——

  日期：——
• Barboni, Luciano; Bartoli, Giuseppe; Marcantoni, Enrico, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2133 - 2138
  作者：Barboni, Luciano、Bartoli, Giuseppe、Marcantoni, Enrico、Petrini, Marino、Dalpozzo, Renato

  DOI：——

  日期：——
• Synthesis of pyrrolidines and pyrrolidinones by the rhodium complex catalyzed cyclization of unsaturated amines
  作者：Jian Qiang Zhou、Howard Alper

  DOI：10.1021/jo00038a019

  日期：1992.6

  N-Allylic arylamines react with carbon monoxide, sodium borohydride, 2-propanol, and catalytic amounts of the zwitterionic complex eta-6-C6H6BPh3-Rh(COD)+ (1), to form pyrrolidines as the main products in most cases. Pyrrolidinones result from N-allylic alkylamines. An alternate route to the lactams from N-allylic alkylamines involves synthesis gas instead of CO/NaBH4, together with the dual catalytic system 1/[Ru(CO)3Cl2]2. Complementary to the N-allylic arylamine route to pyrrolidines with NaBH4 and 1 is the use of synthesis gas, 1, and 1,4-bis(diphenylphosphino)butane.