(N-deutero-phenyl-methylene)-aniline | 3947-93-1

• 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-deutero-phenyl-methylene)-aniline
• 英文别名: N-benzylidenaniline-d1；Benzylidenanilin-d(1)；N-α-Deuterio-benzyliden-anilin；(α-D)-N-Benzyliden-anilin；N-(deuterio-phenyl-methylene)-aniline；(α-²H1)-Benzalanilin；α-Deuterio-benzyliden-anilin；α-Deutero-benzyliden-anilin；1-deuterio-N,1-diphenylmethanimine
• CAS: 3947-93-1
• 化学式: C₁₃H₁₁N
• 分子量: 182.229
• InChiKey: UVEWQKMPXAHFST-WORMITQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (N-deutero-phenyl-methylene)-aniline 在 异丙基氯化镁 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 N-(2-(N-(phenyl)-1-(4-methoxyphenyl)-2-D-2-phenylethyl))-P,P-diphenylphosphinic amide 、 N-(2-(N-(phenyl)-1-(4-methoxyphenyl)-2-D-2-phenylethyl))-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  Synthesis of Aryl anti-Vicinal Diamines via Aza-Brook Rearrangement-Initiated Nucleophilic Addition of α-Silylamines to Imines

  摘要：

  An efficient protocol is described for the synthesis of vicinal diamines via aza-Brook rearrangement-initiated nucleophilic addition of alpha-silylamines to imines. Various symmetrical and unsymmetrical aryl diamine derivatives were prepared in moderate to high yields with high anti/syn diastereoselectivity.

  DOI：

  10.1021/acs.joc.5b00255
• 作为产物：
  描述：

  N-苄叉苯胺 在 氘代甲醇 、 4-(diphenylphosphino)-1,3-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazoliumhexafluorophosphate 、 potassium tert-butylate 作用下， 反应 72.0h， 以98%的产率得到(N-deutero-phenyl-methylene)-aniline
  参考文献：
  名称：

  甲酰基上的中离子碳烯（MIC）催化的H / D交换

  摘要：

  甲酰基上的H / D交换是合成氘代醛的最直接方法。铂族金属络合物已被用于催化这种转化，但存在明显的底物范围限制。尽管N-杂环卡宾也可以通过形成Breslow中间体来激活醛的C–H键，但安息香缩合和其他C–C键形成途径迄今已超过了合成上有用的H / D交换。醛与1,2,3-三唑啉的反应研究表明，可逆地形成布雷斯洛中间体，并抑制了甲醇溶剂中的缩合步骤。使用氘代甲醇作为负担得起的D源，1,2,3-三唑基亚烷基以高收率和氘掺入水平催化芳基，烯基和烷基醛的H / D交换。

  DOI：

  10.1016/j.chempr.2019.08.011

文献信息

• Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
  作者：Keshav Paudel、Shi Xu、Oleksandr Hietsoi、Bedraj Pandey、Chuka Onuh、Keying Ding

  DOI：10.1021/acs.organomet.0c00727

  日期：2021.2.8

  Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading

  本文介绍了由三脚架配体支撑的明确定义的钴配合物催化的可转换亚胺和胺合成。各种各样的伯醇和胺以良好至极好的收率选择性地转化为亚胺或胺。发现该碱在选择性上起关键作用。催化量的碱导致亚胺的形成，而碱的过量负载导致胺产物。这种关于产物选择性的策略也强烈地取决于所使用的有机金属催化剂。我们希望本研究可以为选择性有机合成和催化剂设计提供有用的见识。
• Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water
  作者：Chenyang Ge、Xinxin Sang、Wei Yao、Liang Zhang、Dawei Wang

  DOI：10.1039/c7gc02892j

  日期：——

  indazolyl-pyridinyl-triazole ligand was synthesized and its iridium complex supported on hydrotalcite was characterized via X-ray power diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray (EDX) spectroscopy and transmission electron microscopy (TEM). This new heterogeneous catalyst bearing the unsymmetrical indazolyl-pyridinyl-triazole ligand exhibits high catalytic activity

  在此，合成了吲唑基-吡啶基-三唑配体，并通过X射线功率衍射（XRD），X射线光电子能谱（XPS），能量色散X射线（EDX）光谱和透射表征了负载在水滑石上的铱配合物。电子显微镜（TEM）。这种带有不对称吲唑基-吡啶基-三唑配体的新型多相催化剂在水中表现出很高的催化活性。通过在清洁条件下转移氢化和脱氢，使苄胺与芳胺进行具有挑战性的选择性反应，从而获得了官能化的胺和亚胺。特别地，观察到该催化剂体系在水中显示出良好的回收性能。机理研究表明，这种转变是通过胺的脱氢，水解和缩合过程。反应中间体的直接捕获为该过程提供了充分的证据。
• One-pot synthesis of Schiff base compounds <i>via</i> photocatalytic reaction in the coupled system of aromatic alcohols and nitrobenzene using CdIn₂S₄ photocatalyst
  作者：Xiangju Ye、Yinghao Chen、Cancan Ling、Ran Ding、Xuchun Wang、Xuemei Zhang、Shifu Chen

  DOI：10.1039/c8dt02278j

  日期：——

  photocatalytic performance of the CdIn2S4 photocatalyst was evaluated using photocatalytic synthesis of Schiff base compounds in a coupled system of aromatic alcohols and nitrobenzene under visible light irradiation. The yield of N-benzylideneaniline reached up to 32% in the coupled system of benzyl alcohol and nitrobenzene under visible light illumination for 8 h. Furthermore, the changes for the

  在温和条件下利用太阳能驱动有机反应为绿色合成提供了可持续的途径，并且一直是科学家追求的主要目标之一。在这项研究中，使用简单的溶剂热方法制备了硫化镉铟（CdIn 2 S 4）光催化剂，并利用X射线粉末衍射，紫外可见吸收光谱，氮吸附-解吸等温线，扫描电子显微镜，透射光谱对其进行了全面表征。电子显微镜和X射线光谱测量。CdIn 2 S 4的光催化性能在可见光照射下，在芳香族醇和硝基苯的偶联体系中，通过光催化合成席夫碱化合物来评估光催化剂。在可见光照射下，在苄醇和硝基苯的偶合体系中，N-苄叉基苯胺的收率达到32％。此外，还研究了光催化过程中作为中间产物的芳香醛和铝的量的变化。使用同位素示踪，一种光催化合成N的可能反应机理提出了亚苄基苯胺和苄醇与硝基苯偶联体系中的氧化还原反应。希望该策略可以为在温和条件下使用光催化技术进行传统有机合成和转化提供有效途径。
• Desulfurization and H-Migration of Secondary Thioamides Catalyzed by an Iron Complex to Yield Imines and Their Reaction Mechanism
  作者：Kozo Fukumoto、Akane Sakai、Kazumasa Hayasaka、Hiroshi Nakazawa

  DOI：10.1021/om400304v

  日期：2013.5.24

  Secondary thioamides were converted into imines as the major products using hydrosilane in the presence of an iron catalyst. An iron carbene complex with a silyl thiolato ligand was isolated as one of the intermediates of the catalytic cycle and was characterized by X-ray analysis.
• Formation of Imino−Phosphine Bidentate Chelates by an Unprecedented Organopalladium Complex Promoted Oxidative Coupling Reaction between Diphenylvinylphosphine and Imines
  作者：Xueming Liu、K. F. Mok、Jagadese J. Vittal、Pak-Hing Leung

  DOI：10.1021/om000416l

  日期：2000.9.1

  Oxidative coupling reaction between Ph2P-CH=CH2 and a series of imines PI IC(R)=N(R') [where R = H, D; R' = H, Ph, p-Me(C6H4), p-Cl(C6H4), p-MeO(C6H4)] in the presence of(S)-ortho-palladated[1-(dimethylamino)ethyl]naphthylene as the reaction template produced the unexpected imino-phosphine ligands (R')N=C-C(=CPhR)PPh2 where the P,N-bidentate chelates to the chiral palladium template. The coupling reactions initially adopted a [2+2] cycloaddition mechanism followed by the ring-opening pathway to generate the acyclic ligands. The rate of these coupling reactions was affected by the electronic properties of the R' group on the imines. No coupling reaction was observed between Ph2P-CH=CH2 and p-CF3(C6H4)N=CPh(H), which contains a strong electronic withdrawing group at the p-position. In all the product complexes the nitrogen donors from the imine and from the naphthylamine chelates are coordinated regiospecifically in the cis positions. Similarly the R substituent and the PPh2 moiety are invariably located in the cis positions on the newly generated C=C bonds. The imino-phosphine chelates are stable in strong sulfuric acid, while the naphthylamine moiety in the template complexes is removed chemoselectively in the presence of this acid. Upon the removal of the naphthylamine chelate, the imino-phosphines could be liberated from palladium by the treatment with aqueous cyanide. Except far HN=C-C(=CPhH)PPh2, which decomposed readily in aqueous solution, all the other Liberated imino-phosphines were obtained as air-stable low-melting solids.