tert-butyl (1,2-diphenylethyl)carbamate | 695231-57-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: tert-butyl (1,2-diphenylethyl)carbamate
• 英文别名: (1,2-Diphenyl-ethyl)-carbamic acid tert-butyl ester；1,1-Dimethylethyl N-(1,2-diphenylethyl)carbamate；tert-butyl N-(1,2-diphenylethyl)carbamate
• CAS: 695231-57-3
• 化学式: C₁₉H₂₃NO₂
• mdl: MFCD24393177
• 分子量: 297.397
• InChiKey: KEQOOSZELYDOFA-UHFFFAOYSA-N

物化性质

• 沸点：
  422.4±34.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.315
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (1,2-diphenylethyl)carbamate 在 水 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1,2-二苯基乙胺
  参考文献：
  名称：

  Deprotection of a primary Boc group under basic conditions

  摘要：

  Treatment of a primary t-butyl carbamate (Boc) group with excess sodium t-butoxide in slightly wet tetrahydrofuran or 2-methyltetrahydrofuran provides the corresponding primary amine in excellent yield. We believe the reaction proceeds through ail isocyanate intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.108
• 作为产物：
  描述：

  (1,2-Diphenyl-ethyl)-[(S)-1-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以79%的产率得到tert-butyl (1,2-diphenylethyl)carbamate
  参考文献：
  名称：

  ‘meso-Selective’ functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

  摘要：

  Lithiation and methylation of amide and carbamate derivatives of alpha-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-alpha-methylbenzylamine derivatives, Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-alpha-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00154-5

文献信息

• The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines
  作者：Diane E. Carrera

  DOI：10.1039/c7cc04397j

  日期：——

  salts to imine and enamine electrophiles is reported. Use of the pre-activated trifluoroboronate complex bypasses the need for α-hetero substitution on the electrophile component, greatly expanding the scope of the Petasis borono–Mannich reaction. A variety of vinyl, aromatic and heteroaromatic trifluoroborate salts undergo addition with good efficiency under mild reaction conditions. The reaction is amenable

  据报道，酸促进了有机三氟硼酸盐向亚胺和烯胺亲电子试剂的加成。预活化的三氟硼酸酯络合物的使用绕开了亲电试剂组分上α-杂原子取代的需要，大大扩展了Petasis borono-Mannich反应的范围。在温和的反应条件下，各种乙烯基，芳族和杂芳族三氟硼酸盐都可以高效地加成。该反应适合与各种氨基甲酸酯保护的亚胺和烯胺亲电子试剂一起使用，首次实现与脂族醛的有效偶联。
• Direct Amination of Benzylic Pinacol Boronates by an Aminoazanium
  作者：Chao Liu、Jianeng Xu、Yucheng Qin

  DOI：10.1055/a-2028-5646

  日期：——

  A practical stereospecific direct amination of benzylic pinacol boronates was achieved by using 4-amino-4-methylmorpholinium iodide as a new amination reagent and cesium carbonate as the base. After amination, an in situ reductive N-alkylation with an aldehyde proceeded well to produce secondary amines.

  以 4-amino-4-methylmorpholinium iodide 作为新型胺化试剂，以碳酸铯为碱，实现了苄基频哪醇硼酸盐的实用立体特异性直接胺化。胺化后，用醛进行原位还原 N-烷基化，生成仲胺。