N-(diphenylmethylidene)-1-cyclohexylmethylamine | 51411-38-2

• 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)-1-cyclohexylmethylamine
• 英文别名: N-cyclohexylmethyl benzophenone imine；N-(Cyclohexylmethyl)-diphenylmethan；Benzophenon-N-cyclohexylmethylimin；Cyclohexanemethanamine, N-(diphenylmethylene)-；N-(cyclohexylmethyl)-1,1-diphenylmethanimine
• CAS: 51411-38-2
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: XASFYEAPFVFTEN-UHFFFAOYSA-N

物化性质

• 沸点：
  150-155 °C(Press: 0.8 Torr)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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)-1-cyclohexylmethylamine 在 盐酸 作用下， 生成 环己甲胺
  参考文献：
  名称：

  Kauffmann,T. et al., Chemische Berichte, 1977, vol. 110, p. 2659 - 2664

  摘要：

  DOI：
• 作为产物：
  描述：

  N-diphenylmethylcyclohexylmethylamine 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 N-(diphenylmethylidene)-1-cyclohexylmethylamine
  参考文献：
  名称：

  Oxidative Deprotection of Diphenylmethylamines

  摘要：

  [GRAPHICS]The diphenylmethyl amino protecting group can be efficiently removed by initial oxidation of the amine to an imine by 2,3-dichloro-5,6-dicyanobenzoquinone. The resulting imine can then be easily hydrolyzed under mildly acidic conditions. This method is particularly well suited for the preparation of alpha-amino phosphinates and alpha-amino phosphonates.

  DOI：

  10.1021/ol990956i

文献信息

• Tropylium Ion Mediated α-Cyanation of Amines
  作者：Julia M. Allen、Tristan H. Lambert

  DOI：10.1021/ja109617y

  日期：2011.2.9

  Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total

  描述了 Tropylium 离子介导的胺的 α-氰化。即使在 KCN 存在下，托鎓离子也能氧化各种胺底物，生成的亚胺离子与氰化物离子发生盐复分解反应生成氨基腈。这种转化的副产品只是环庚三烯（一种挥发性烃）和水溶性四氟硼酸钾。显示了 α-氰化过程的 13 种总底物，包括 17β-氰基半胱氨酸的克级合成。此外，还证明了 tropylium 离子介导的氧化氮杂-Cope 重排。
• Hullot,P.; Cuvigny,T., Bulletin de la Societe Chimique de France, 1973, p. 2989 - 2992
  作者：Hullot,P.、Cuvigny,T.

  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.
• KAUFFMANN T.; BERG H.; KOEPPELMANN E.; KUHLMANN D., CHEM. BER. <CHBE-AM>, 1977, 110, NO 7, 2659-2664
  作者：KAUFFMANN T.、 BERG H.、 KOEPPELMANN E.、 KUHLMANN D.

  DOI：——

  日期：——
• Oxidative Deprotection of Diphenylmethylamines
  作者：Peter B. Sampson、John F. Honek

  DOI：10.1021/ol990956i

  日期：1999.11.1

  [GRAPHICS]The diphenylmethyl amino protecting group can be efficiently removed by initial oxidation of the amine to an imine by 2,3-dichloro-5,6-dicyanobenzoquinone. The resulting imine can then be easily hydrolyzed under mildly acidic conditions. This method is particularly well suited for the preparation of alpha-amino phosphinates and alpha-amino phosphonates.