N,N-dimethylaniline-2,4,6-d₃ | 7217-47-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethylaniline-2,4,6-d₃
• 英文别名: N,N-dimethyl-2,4,6-trideuterioaniline；[²H]-N,N-dimethylaniline；2,4,6-trideuterio-N,N-dimethyl-aniline；2,4,6-Trideuterio-N,N-dimethyl-anilin；N.N-Dimethyl<2.4.6²H3>anilin；2,4,6-Trideutero-N,N'-dimethylaminobenzol；Benzen-2,4,6-d3-amine, N,N-dimethyl-；2,4,6-trideuterio-N,N-dimethylaniline
• CAS: 7217-47-2
• 化学式: C₈H₁₁N
• 分子量: 124.158
• InChiKey: JLTDJTHDQAWBAV-YXAOJZFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  氘代碘甲烷 、 N,N-dimethylaniline-2,4,6-d₃ 生成 phenyl-d3 trimethylammonium iodide
  参考文献：
  名称：

  Penner, Glenn H.; Polson, James M.; Daleman, Stephen I., Canadian Journal of Chemistry, 1993, vol. 71, # 4, p. 417 - 426

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 十二羰基三钌 、 重水 作用下， 反应 12.0h， 以95%的产率得到N,N-dimethylaniline-2,4,6-d₃
  参考文献：
  名称：

  Ru（0）催化的N-烷基取代的苯胺区域选择性氘化的简便方法

  摘要：

  描述了一种以Ru 3（CO）12（⩽1mol％）作为催化剂和D 2 O作为氘源的N-烷基取代的苯胺区域选择性氘化的高效且实用的方法。在中性条件下，相对于氮，在邻位和/或对位有效地氘化了多种N-烷基取代的苯胺（最高达98％）。在当前条件下，可以通过简单的萃取和蒸发容易地获得氘代苯胺。与先前的方法相比，具有芳族甲氧基的取代基不会影响选择性。

  DOI：

  10.1016/j.tetlet.2014.07.071

文献信息

• Direct <i>para</i>-C–H heteroarylation of anilines with quinoxalinones by metal-free cross-dehydrogenative coupling under an aerobic atmosphere
  作者：Jun Xu、Lin Huang、Lei He、Chenfeng Liang、Yani Ouyang、Jiabin Shen、Min Jiang、Wanmei Li

  DOI：10.1039/d1gc01899j

  日期：——

  Herein, a green and efficient metal-free cross-dehydrogenative coupling (CDC) for the direct para-C–H heteroarylation of anilines with quinoxalinones has been described. This reaction is performed in H2O/DMSO (v/v = 2 : 1) using air as the sole oxidant. Various anilines (primary, secondary and tertiary amines) and quinoxalinones are well compatible, affording the corresponding products in moderate-to-good

  本文描述了一种绿色且高效的无金属交叉脱氢偶联（CDC），用于苯胺与喹喔啉酮的直接对-C-H 杂芳基化。该反应在 H 2 O/DMSO (v/v = 2:1) 中进行，使用空气作为唯一氧化剂。各种苯胺（伯胺、仲胺和叔胺）和喹喔啉酮具有良好的相容性，以中等至良好的产率提供相应的产品。这种方法为含氮化合物的后期改性提供了一种环境友好且有效的替代方法。
• Dehalogenative Deuteration of Unactivated Alkyl Halides Using D₂O as the Deuterium Source
  作者：Aiyou Xia、Xin Xie、Xiaoping Hu、Wei Xu、Yuanhong Liu

  DOI：10.1021/acs.joc.9b02026

  日期：2019.11.1

  The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis

  已经开发出使用D 2 O或H 2 O作为氘或氢供体的锌与烷基卤化物的一般脱卤。该方法在温和的反应条件下为底物范围较宽的氘标记衍生物提供了一种高效经济的方法。机理研究表明，自由基过程涉及有机锌中间体的形成。有机锌中间体的容易水解为该转化提供了驱动力。
• Diastereoselective Tandem Addition−Cyclization Reactions of Unsaturated Tertiary Amines Initiated by Photochemical Electron Transfer (PET)
  作者：Samuel Bertrand、Norbert Hoffmann、Stéphane Humbel、Jean Pierre Pete

  DOI：10.1021/jo001166l

  日期：2000.12.1

  Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of or-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is greater than or equal to 90%. The alpha -aminoalkyl radicals were produced from tertiary amines by photachemical-induced electron transfer. When N,N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of 1 during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tettahydroquinolines 21a-i, 22a-f, and 26g-i were doubled.
• Penner, Glenn H.; Polson, James M.; Daleman, Stephen I., Canadian Journal of Chemistry, 1993, vol. 71, # 4, p. 417 - 426
  作者：Penner, Glenn H.、Polson, James M.、Daleman, Stephen I.、Reid, Kara

  DOI：——

  日期：——
• A convenient method for the Ru(0)-catalyzed regioselective deuteration of N-alkyl-substituted anilines
  作者：Miao Zhan、Hongxia Jiang、Xuehai Pang、Tao Zhang、Ruixue Xu、Lifeng Zhao、Yu Liu、Yu Gong、Yuanwei Chen

  DOI：10.1016/j.tetlet.2014.07.071

  日期：2014.9

  A highly effective and operationally practical method for the regioselective deuteration of N-alkyl-substituted anilines employing Ru3(CO)12 (⩽1 mol %) as catalyst and D2O as deuterium source was described. A variety of N-alkyl-substituted anilines were efficiently deuterated (up to 98%) at the ortho and/or para position with respect to the nitrogen at neutral conditions. Under the present conditions

  描述了一种以Ru 3（CO）12（⩽1mol％）作为催化剂和D 2 O作为氘源的N-烷基取代的苯胺区域选择性氘化的高效且实用的方法。在中性条件下，相对于氮，在邻位和/或对位有效地氘化了多种N-烷基取代的苯胺（最高达98％）。在当前条件下，可以通过简单的萃取和蒸发容易地获得氘代苯胺。与先前的方法相比，具有芳族甲氧基的取代基不会影响选择性。