N-(diphenylmethylidene)-2,2-dimethylpropylamine | 24590-76-9

• 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-(diphenylmethylidene)-2,2-dimethylpropylamine
• 英文别名: N-neopentylbenzophenone imine；N-(Benzhydryliden)neopentylamin；1-Propanamine, N-(diphenylmethylene)-2,2-dimethyl-；N-(2,2-dimethylpropyl)-1,1-diphenylmethanimine
• CAS: 24590-76-9
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: RSAJNNCDOXNSRL-UHFFFAOYSA-N

物化性质

• 沸点：
  338.6±15.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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-(diphenylmethylidene)-2,2-dimethylpropylamine 、 氯甲酸苄酯 在 盐酸 、 potassium carbonate 作用下， 生成 benzyl N-(2,2-dimethylpropyl)carbamate
  参考文献：
  名称：

  Efficient Transamination under Mild Conditions:  Preparation of Primary Amine Derivatives from Carbonyl Compounds via Imine Isomerization with Catalytic Amounts of Potassium tert-Butoxide

  摘要：

  1,3-Prototropic rearrangement of N-diphenylmethanimines was successfully performed with a catalytic amount of potassium tert-butoxide. This procedure can also be used with aliphatic and aromatic aldimines and was extended to the isomerization of (1R)-camphorquinone monoimine and N-(4-methoxyphenyl)-4-phenyl-3-iminoazetidin-2-one. The isomerized imines were easily hydrolyzed and isolated as Cbz derivatives.

  DOI：

  10.1021/jo952124d
• 作为产物：
  描述：

  三甲基乙腈 在 lithium aluminium tetrahydride 、 zinc(II) chloride 作用下， 以 乙醚 、 苯 为溶剂， 生成 N-(diphenylmethylidene)-2,2-dimethylpropylamine
  参考文献：
  名称：

  Studies in stereochemistry. XL. Unusual magnitudes of optical rotations of imines of neopentylamine-1-d and ethylamine-1-d

  摘要：

  DOI：

  10.1021/ja01044a023

文献信息

• Reductive Elimination to Form C(sp³)–N Bonds from Palladium(II) Primary Alkyl Complexes
  作者：D. Matthew Peacock、Quan Jiang、Thomas R. Cundari、John F. Hartwig

  DOI：10.1021/acs.organomet.8b00617

  日期：2018.10.8

  Reductive eliminations to form alkyl–nitrogen bonds are rare, and examples of this reaction from isolated complexes containing simple, unstabilized primary alkyl groups have not been observed. We report the synthesis of stable neopentylpalladium(II) anilido and methyleneamido complexes that undergo reductive elimination to form the C(sp3)–N bonds in N-neopentyl anilines and N-neopentyl imines, respectively

  还原消除形成烷基-氮键的现象很少见，而且还没有观察到由含有简单的，不稳定的伯烷基的孤立配合物引起的反应实例。我们报告了合成的稳定的新戊基钯（II）苯胺和亚氨基酰胺配合物，经过还原消除形成N-新戊基苯胺和N中的C（sp 3）-N键-新戊基亚胺。这些配合物的合成和分离是通过P，O辅助配体对钯的弱螯合实现的。DFT计算表明，新戊基钯（II）络合物通过协同作用机理进行还原消除，该协同作用机理类似于烷基配体向氧的迁移，或者在供体最初解离之后或与Pd-O键的延长相一致，具体取决于身份反应的和辅助的配体。
• Darstellung und eigenschaften von N-(diphenylmethylen)-triorganoelement-methylaminen (element = C, Si, Ge, Sn)
  作者：E. Popowski、A. Hahn、H. Kelling

  DOI：10.1016/s0022-328x(00)82488-2

  日期：1976.4

  N-(Diphenylmethylene)triorganoelement-methylamines, (C6H5)2CNCH2MR3 (M  C, Si, Ge, Sn), have been prepared by treatment of triorganoelement halides with 1,1-diphenyl-2-azaallyllithium. The IR, UV and NMR data of these compounds are discussed and compared with the spectroscopic data of the corresponding allyl compounds. As in allyl compounds these data can only be explained by assuming conjugative

  ñ - （二苯基亚甲基）triorganoelement-甲胺，（C 6 H ^ 5）2 CNCH 2 MR 3（MC，硅，锗，锡），已经制备由治疗triorganoelement卤化物与1,1-二苯基2-氮杂烯丙基锂。讨论了这些化合物的IR，UV和NMR数据，并将其与相应的烯丙基化合物的光谱数据进行了比较。与烯丙基化合物一样，这些数据只能通过假设M和N = C基团之间发生共轭相互作用来解释。
• Electrochemical Ni‐Catalyzed Decarboxylative C(sp³)−N Cross‐Electrophile Coupling
  作者：Yue‐Ming Cai、Xiao‐Ting Liu、Lin‐Lin Xu、Ming Shang

  DOI：10.1002/anie.202315222

  日期：2024.3.18

  Ni-catalyzed decarboxylative C(sp3)−N cross-coupling of redox active ester and oxime esters was realized through electrochemical cathodic reduction. Mechanistic studies unveil a high-valent nickel species-driven reductive elimination pathway, rather than direct radical-radical coupling. The utility of this methodology was demonstrated through a broad scope (1°, 2°, 3° carboxylic acids) and late-stage

  通过电化学阴极还原实现了氧化还原活性酯和肟酯的镍催化脱羧C(sp 3 )−N交叉偶联。机理研究揭示了高价镍物质驱动的还原消除途径，而不是直接的自由基-自由基耦合。该方法的实用性通过复杂分子的广泛范围（1°、2°、3°羧酸）和后期功能化得到了证明。
• Rhodes, Christopher J.; Agirbas, Hikmet, Journal of the Chemical Society. Perkin transactions II, 1992, # 3, p. 397 - 402
  作者：Rhodes, Christopher J.、Agirbas, Hikmet

  DOI：——

  日期：——
• Efficient Transamination under Mild Conditions:  Preparation of Primary Amine Derivatives from Carbonyl Compounds <i>via</i> Imine Isomerization with Catalytic Amounts of Potassium <i>tert</i>-Butoxide
  作者：Gianfranco Cainelli、Daria Giacomini、Alessandra Trerè、Pietro Pilo Boyl

  DOI：10.1021/jo952124d

  日期：1996.1.1

  1,3-Prototropic rearrangement of N-diphenylmethanimines was successfully performed with a catalytic amount of potassium tert-butoxide. This procedure can also be used with aliphatic and aromatic aldimines and was extended to the isomerization of (1R)-camphorquinone monoimine and N-(4-methoxyphenyl)-4-phenyl-3-iminoazetidin-2-one. The isomerized imines were easily hydrolyzed and isolated as Cbz derivatives.