Benzyldimethylamine-α,α-d₂ | 38161-07-8

• 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: Benzyldimethylamine-α,α-d₂
• 英文别名: N,N-dimethyl(benzyl-d2)amine；N,N-dimethyl-1-phenyl(methan-d2)amine；N,N-dimethyl-1-phenylmethanamine-d₂；N.N-Dimethyl-α-dideuterobenzylamin；N,N-Dimethyl-<α-2H2>-benzylamin；(dideuterio-phenyl-methyl)-dimethyl-amine；Dimethyl<2H>(2)benzylamin；N,N-Dimethylbenzylamin-α-D(2)；1,1-dideuterio-N,N-dimethyl-1-phenylmethanamine
• CAS: 38161-07-8
• 化学式: C₉H₁₃N
• 分子量: 137.193
• InChiKey: XXBDWLFCJWSEKW-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzyldimethylamine-α,α-d₂ 在 1,4-二甲基萘1,4-内过氧化物 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 苯甲醛-α-d1 、 N-methyl-N-(benzyl-α,α-d2)formamide
  参考文献：
  名称：

  单线态氧对苄基二甲基胺的氧化作用。产品与机制。

  摘要：

  [反应：见正文]进行了苄基二甲基胺（1）与热和光化学生成的1O2在MeCN中反应的产物研究。苯甲醛和N-苄基-N-甲基甲酰胺是反应产物，氧合代表约。1O2整体淬灭的9％。还测定了温度效应以及分子间和分子内动力学氘同位素效应。建议产物源自可逆形成的电荷转移络合物中的内部络合物氢原子转移。

  DOI：

  10.1021/ol047876l
• 作为产物：
  描述：

  N,N-二甲基苯甲酰胺 在 (5-溴-1-苯并噻吩-2-基)硼酸 、 二苯基(硅烷-d2) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以43%的产率得到Benzyldimethylamine-α,α-d₂
  参考文献：
  名称：

  硼酸催化的氢化硅烷化将酰胺选择性还原为胺

  摘要：

  不是'B'ore！在存在氢硅烷的情况下，基于苯并噻吩的硼酸催化叔，仲和伯酰胺的还原。该反应显示出良好的官能团耐受性。

  DOI：

  10.1002/anie.201304495

文献信息

• Heterogeneous Catalytic Reduction of Tertiary Amides with Hydrosilanes Using Unsupported Nanoporous Gold Catalyst
  作者：Yuhui Zhao、Sheng Zhang、Yoshinori Yamamoto、Ming Bao、Tienan Jin、Masahiro Terada

  DOI：10.1002/adsc.201900838

  日期：2019.10.22

  We have demonstrated that the unsupported nanoporous gold (AuNPore) was a green and highly efficient heterogeneous catalyst for the reduction of amides to amines using hydrosilanes as reductants. A variety of tertiary amides with a broad functional groups were reduced to the corresponding tertiary amines in the presence of 2 mol% of AuNPore and PheMe2SiH or (Me2SiH)2O under mild conditions. AuNPore

  我们已经证明，无载体的纳米孔金（AuNPore）是一种绿色高效的非均相催化剂，用于使用氢化硅烷作为还原剂将酰胺还原为胺。在温和的条件下，在2 mol％的AuNPore和PheMe 2 SiH或（Me 2 SiH）2 O的存在下，各种具有广泛官能团的叔酰胺被还原为相应的叔胺。通过简单的过滤回收AuNPore催化剂，并使用十二次而没有任何催化活性的损失。AuNPore /氢硅烷体系也成功地用于亚砜和N-氧化物的硅氢化还原。
• Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance
  作者：Shoubhik Das、Daniele Addis、Shaolin Zhou、Kathrin Junge、Matthias Beller

  DOI：10.1021/ja910083q

  日期：2010.2.17

  A novel zinc-catalyzed reduction of tertiary amides was developed. This system shows remarkable chemoselectivity and substrate scope tolerating ester, ether, nitro, cyano, azo, and keto substituents.

  开发了一种新型的锌催化还原叔酰胺。该系统显示出显着的化学选择性和底物范围，可耐受酯、醚、硝基、氰基、偶氮和酮基取代基。
• A convenient synthesis of deuterium labeled amines and nitrogen heterocycles with KOt-Bu/DMSO-d6
  作者：Yu Hu、Liang Liang、Wen-tao Wei、Xiang Sun、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tet.2015.01.015

  日期：2015.3

  H/D exchanges of arylmethyl amines and nitrogen heterocycles were conveniently achieved with KOt-Bu/DMSO-d6. The method is also applicable for phenyl benzyl ethers, diarylmethanes, and alkyl arenes. These H/D exchange reactions are suggested to proceed via a free radical pathway.

  芳基甲胺和氮杂环的H / D交换可通过KO t -Bu / DMSO- d 6方便地实现。该方法也适用于苯基苄基醚，二芳基甲烷和烷基芳烃。这些H / D交换反应被建议通过自由基途径进行。
• Azetidines. 5. Reaction of 1,1,3,3-tetramethyl- and 1-benzyl-1,3,3-trimethylazetidinium ions with butyllithium and phenyllithium. Deuterium labeling as a mechanistic probe
  作者：Max. T. Wills、Irene E. Wills、Lawrence Von Dollen、Barry L. Butler、John Porter、Arthur G. Anderson

  DOI：10.1021/jo01300a046

  日期：1980.6
• Hypervalent Ammonium Radicals. Effects of Alkyl Groups and Aromatic Substituents
  作者：Scott A. Shaffer、Martin Sadílek、František Tureček

  DOI：10.1021/jo960320u

  日期：1996.1.1

  Neutralization by collisional electron transfer of gaseous benzylalkylammonium ions produces transient hypervalent radicals whose dissociations depend on the substituents in the aromatic ring and at the amine nitrogen atom. Benzylammonium radical, C6H5CH2NH3 ., dissociates mainly by N-H bond cleavage to give benzylamine. Dissociation of the CH2-N bond to benzyl radical and ammonia is less abundant. Benzylmethylammonium, C6H5CH2NH2CH3 ., dissociates by CH2-N, N-CH3, and N-H bond cleavages to give methylamine, benzyl radical, benzylamine, and N-methylbenzylamine. Benzyldimethylammonium, C6H5CH2NH(CH3)(2) . undergoes loss of dimethylamine and hydrogen, while the loss of methyl is less important. (2,3,4,5,6-Pentafluorobenzyl)dimethylammonium radical, C6F5CH2NH(CH3)(2) ., dissociates mainly by fission of the pentafluorophenyl ring to give CnFm fragments with CF . as the dominating product, while bend dissociations at the hypervalent nitrogen atom are less important. The relative stabilities of pentafluorobenzyl and tropyl cations and radicals are assessed by ab initio calculations. (3,5-Dinitrobenzyl)dimethylammonium radical, (NO2)(2)C6H3CH2NH(CH3)(2) . undergoes competitive losses of hydrogen and NO and intramolecular proton transfer onto the dinitrophenyl ring. Mechanisms for these reactions are suggested involving dissociative electron attachment at the aromatic ring and formation of hypervalent ammonium radicals and zwitterionic intermediates.