α-methyl-N-(1-methyl-3-phenylpropyl)benzenepropanamine | 795-22-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: α-methyl-N-(1-methyl-3-phenylpropyl)benzenepropanamine
• 英文别名: opt.-inakt. Bis-<4-phenyl-but-2-yl>-amin；bis(4-phenyl-2-butyl)amine；bis-(1-methyl-3-phenyl-propyl)-amine；4-phenyl-N-(4-phenylbutan-2-yl)butan-2-amine
• CAS: 795-22-2
• 化学式: C₂₀H₂₇N
• 分子量: 281.441
• InChiKey: KYUQPTYVJSSFLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-苯基-2-丁醇 在 [Cp*Ir(NH₃)3]I₂ 、 氨 作用下， 以 水 为溶剂， 反应 24.0h， 以63%的产率得到α-methyl-N-(1-methyl-3-phenylpropyl)benzenepropanamine
  参考文献：
  名称：

  Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes

  摘要：

  Novel water-soluble Cp*Ir-ammine complexes have been synthesized, and a new and highly atom-economical system for the synthesis of organic amines using aqueous ammonia as a nitrogen source has been developed. With a water-soluble and air-stable Cp*Ir-ammine catalyst, [Cp*Ir(NH3)(3)][1](2), a variety of tertiary and secondary amines were synthesized by the multialkylation of aqueous ammonia with theoretical equivalents of primary and secondary alcohols. The catalyst could be recycled by a facile procedure maintaining high activity. A one-flask synthesis of quinolizidine starting with 1,5,9-nonanetriol was also demonstrated. This new catalytic system would provide a practical and environmentally benign methodology for the synthesis of various organic amines.

  DOI：

  10.1021/ja107274w

文献信息

• Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines
  作者：Pandula T. Kirinde Arachchige、Hanbin Lee、Chae S. Yi

  DOI：10.1021/acs.joc.8b00649

  日期：2018.5.4

  found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to

  从四核Ru-H与邻苯二酚配体（1 / L1）配合物原位生成的催化体系被发现对于两个伯胺的直接脱氨反应形成仲胺是有效的。催化剂1 / L1具有高度化学选择性，可促进两种不同伯胺的偶联，从而获得不对称仲胺。苯胺与伯胺的类似偶联形成芳基取代的仲胺。用4-甲氧基苄胺处理苯胺-d 7导致偶联产物在CH 2上具有明显的氘掺入（18％D）。在从4-甲氧基苄胺的偶联反应中分离出的产物的α-碳上观察到最明显的碳同位素效应（C（1）= 1.015（2））。通过测量4-甲氧基苯胺与一系列对位取代的苄胺4-XC 6 H 4 CH 2 NH 2（X = OMe，Me，H，F，CF 3）的偶联反应速率来构建Hammett图（ ρ= −0.79±0.1）。基于这些结果，提出了一种可行的偶联反应机理。催化偶联方法提供了操作上简单且化学选择性的仲胺产物合成，而无需使用任何反应性试剂或形成浪费的副产物。
• An approach to chemoenzymatic DKR of amines in Soxhlet apparatus
  作者：Denys Mavrynsky、Reko Leino

  DOI：10.1016/j.jorganchem.2013.11.005

  日期：2014.6

  thermolabile enzyme and metal catalyst for racemization of amines in chemoenzymatic dynamic kinetic resolution, requiring high temperature of operation, is enabled by carrying out the reaction in modified Soxhlet extraction system. Initial insights into the scope and limitations of the developed reaction system are discussed.

  通过在改良的索氏提取系统中进行反应，可以使热不稳定的酶与金属催化剂共存，从而在化学酶动力学动力学拆分中实现胺的外消旋化，需要高温操作。讨论了对已开发的反应系统的范围和局限性的初步见解。
• REACTION OF ARALKYL KETONE OXIMES WITH CARBON MONOXIDE AND HYDROGEN TO YIELD FORMAMIDES AND SECONDARY AMINES
  作者：Alex Rosenthal、M. Yalpani

  DOI：10.1139/v65-093

  日期：1965.3.1

  not available

  不可用。
• Über die Darstellung papaverinähnlicher Stoffe II
  作者：Alfred Dornow、Albert Frese

  DOI：10.1002/ardp.19522851006

  日期：——
• Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes
  作者：Ryoko Kawahara、Ken-ichi Fujita、Ryohei Yamaguchi

  DOI：10.1021/ja107274w

  日期：2010.11.3

  Novel water-soluble Cp*Ir-ammine complexes have been synthesized, and a new and highly atom-economical system for the synthesis of organic amines using aqueous ammonia as a nitrogen source has been developed. With a water-soluble and air-stable Cp*Ir-ammine catalyst, [Cp*Ir(NH3)(3)][1](2), a variety of tertiary and secondary amines were synthesized by the multialkylation of aqueous ammonia with theoretical equivalents of primary and secondary alcohols. The catalyst could be recycled by a facile procedure maintaining high activity. A one-flask synthesis of quinolizidine starting with 1,5,9-nonanetriol was also demonstrated. This new catalytic system would provide a practical and environmentally benign methodology for the synthesis of various organic amines.