(E)-N-(2,4,6-Trimethylphenylmethylene)benzenamine | 34143-85-6

• 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: (E)-N-(2,4,6-Trimethylphenylmethylene)benzenamine
• 英文别名: (E)-1-mesityl-N-phenylmethanimine；N-[(E)-mesitylmethylene]aniline；((E)-2,4,6-trimethyl-benzyliden)-aniline；2,4,6-Trimethyl-benzaldehyd-(E)-phenylimin；((E)-2,4,6-Trimethyl-benzyliden)-anilin
• CAS: 34143-85-6
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: OEUKMWQCHJILLN-GZTJUZNOSA-N

物化性质

• 沸点：
  349.8±41.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-N-(2,4,6-Trimethylphenylmethylene)benzenamine 以 二氯甲烷 为溶剂， 反应 72.5h， 生成 Methyl (S)-2,2-dimethyl-3-(2,4,6-trimethylphenyl)-3-[N-phenyl-((S)-N',N'-phthaloyl-tert-leucyl)]aminopropionate
  参考文献：
  名称：

  N,N-Phthaloylamino Acids as Chiral Auxiliaries in Asymmetric Mannich-Type Reactions

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19990115)38:1/2<184::aid-anie184>3.0.co;2-e
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 苯胺 以 乙醇 为溶剂， 反应 72.0h， 以94%的产率得到(E)-N-(2,4,6-Trimethylphenylmethylene)benzenamine
  参考文献：
  名称：

  Fast and Efficient Synthesis of Pyrano[3,2-c]quinolines Catalyzed by Niobium(V) Chloride

  摘要：

  报道了一种高效的两步法，通过在温和条件下使用五氯化铌作为催化剂，由醛亚胺和3,4-二氢-2H-吡喃之间的亚胺狄尔斯-阿尔德反应合成吡喃并喹啉衍生物。

  DOI：

  10.1055/s-2008-1067186

文献信息

• Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst
  作者：James R. Lawson、Lewis C. Wilkins、Rebecca L. Melen

  DOI：10.1002/chem.201703109

  日期：2017.8.16

  The metal‐free catalyst tris(2,4,6‐trifluorophenyl)borane has demonstrated its extensive applications in the 1,2‐hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron‐withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient

  无金属催化剂三（2,4,6-三氟苯基）硼烷已证明其在多种不饱和试剂的1,2-氢硼化中具有广泛的应用，这些不饱和试剂包括炔烃，醛和亚胺，其中包括大量的吸电子和捐赠功能。据报道，有超过50种硼化产物，在环境条件下，许多反应都是在低催化剂负载下进行的。在醛和亚胺的情况下，这些频哪醇硼酸酯可以容易地水解以留下相应的醇和胺，而炔基底物产生乙烯基硼烷。这对有机化学家来说具有很大的合成用途。
• Synthesis of Benzhydryl-Substituted Amines by Silanolate-Mediated Aldimine Arylation with Functionalized Aryl Nucleophiles Released from Diazene-Based Reagents
  作者：Aliyaah J. M. Rahman、Lucie Finck、Wolfgang Obermayer、Martin Oestreich

  DOI：10.1021/acs.orglett.2c03798

  日期：2022.12.16

  imine derivatives with functionalized aryl pronucleophiles is reported. The aryl nucleophiles are released from silicon-protected aryl-substituted diazenes by desilylation with potassium trimethylsilanolate concomitant with the loss of dinitrogen. A broad range of functional groups is tolerated in the aryl nucleophile but, depending upon their electronic effect, require specific groups at the imine

  报道了一种无过渡金属的方案，用于N -苯基 - 和N -苯甲酰基取代的苯甲醛衍生亚胺衍生物与功能化芳基亲核试剂的芳基化。芳基亲核试剂通过用三甲基硅烷醇钾进行脱甲硅烷基化并伴随二氮的损失从硅保护的芳基取代的二氮烯中释放出来。芳基亲核试剂可容许多种官能团，但根据它们的电子效应，亚胺氮原子上需要特定的基团。
• Grammaticakis, Bulletin de la Societe Chimique de France, 1951, p. 965,966
  作者：Grammaticakis

  DOI：——

  日期：——
• Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin
  作者：K. Surendra、N. Srilakshmi Krishnaveni、A. Mahesh、K. Rama Rao

  DOI：10.1021/jo052510n

  日期：2006.3.1

  [GRAPHICS]An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of beta-cyclodextrin to afford alpha-aminonitriles in quantitative yields. The use of cyclodextrin precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.
• High degree of exo selectivity in imino Diels-Alder reactions catalyzed by tert-butyldimethylsilyltriflate
  作者：Denise Nogue、Renée Paugam、Lya Wartski

  DOI：10.1016/s0040-4039(00)91597-1

  日期：1992.3

  Diels-Alder reactions of silyloxydiene 1 derived from 1-acetylcyclohexene with imines 2b and 2c occur with high exo selectivity depending upon experimental conditions: exo cycloadducts 3b-c are exclusively formed under kinetic control using tert-butyldimethylsilyltriflate as catalyst. In the presence of AlCl3, under thermodynamic control, high endo selectivity is only observed with 2b.

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