N-(diphenylmethylidene)-2-phenylprop-2-enylamine | 1126650-52-9

• 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-phenylprop-2-enylamine
• 英文别名: N-diphenylmethylidene-2-phenylprop-2-en-1-amine；N-(diphenylmethylidene)-2-phenyl-2-propenylamine；1,1-diphenyl-N-(2-phenylprop-2-enyl)methanimine
• CAS: 1126650-52-9
• 化学式: C₂₂H₁₉N
• 分子量: 297.4
• InChiKey: YFQZGEGXAXCITC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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-phenylprop-2-enylamine 在 N-溴代丁二酰亚胺(NBS) 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-(diphenylmethylidene)-(3-bromo-2-fluoro-2-phenylpropyl)amine
  参考文献：
  名称：

  Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid

  摘要：

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.

  DOI：

  10.1021/jo802791r
• 作为产物：
  描述：

  二苯甲酮亚胺 、 2-phenylallylamine 以 二氯甲烷 为溶剂， 反应 16.0h， 以95%的产率得到N-(diphenylmethylidene)-2-phenylprop-2-enylamine
  参考文献：
  名称：

  Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid

  摘要：

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.

  DOI：

  10.1021/jo802791r

文献信息

• Palladium-Catalyzed Enantioselective C(sp³)–H/C(sp³)–H Umpolung Coupling of <i>N</i>-Allylimine and α-Aryl Ketones
  作者：Tian-Ci Wang、Ling Zhu、Shiwei Luo、Zhong-Sheng Nong、Pu-Sheng Wang、Liu-Zhu Gong

  DOI：10.1021/jacs.1c10721

  日期：2021.12.8

  tolerated to open a convenient and tunable avenue for efficient synthesis of enantioenriched β-amino-γ,δ-unsaturated carbonyl derivatives with high levels of regio- and stereoselectivities, capable of providing a key intermediate for asymmetric synthesis of Focalin. This protocol showcases an umpolung reactivity of the N-allylimines through a concerted proton and two-electron transfer process to cleave

  C(sp 3 )-H 键的不对称功能化是一种有吸引力但具有挑战性的策略，可以实现多种成键事件，从而能够在对官能团进行最少操作的情况下精确组装分子复杂性。在这里，我们报告了N的不对称 C(sp 3 )–H/C(sp 3 )–H umpolung 耦合-烯丙胺和配位α-芳基羰基通过手性亚磷酰胺-钯催化。多种 α-杂芳基酮和 2-酰基咪唑具有良好的耐受性，为高效合成对映富集的 β-氨基-γ,δ-不饱和羰基衍生物开辟了一条方便且可调的途径，具有高水平的区域和立体选择性，能够提供非对称合成 Focalin 的关键中间体。该协议展示了N的 umpolung 反应性-烯丙基亚胺通过协同的质子和双电子转移过程来裂解烯丙基 C-H 键，有效地补充了已建立的烯丙基 C-H 官能化方法。计算研究和实验事实表明，α-杂芳基羰基和 2-酰基咪唑攻击 π-烯丙基钯物种的内球烯丙基化途径，其中与钯中心的氮配位使支链区域选择性的偏好成为可能。
• Rhenium-Catalyzed Regio- and Stereoselective Addition of Imines to Terminal Alkynes Leading to <i>N</i>-Alkylideneallylamines
  作者：Yoshiya Fukumoto、Masato Daijo、Naoto Chatani

  DOI：10.1021/ja3022818

  日期：2012.5.30

  The reaction of terminal allcynes with imines using ReBr(CO)(5) as a catalyst results in the production of N-alkylideneallylamines and not the conventional propargylamines. The substituent on the imine nitrogen is important, and a diphenylmethyl group gave the best result. The catalytic cycle of this regio selective C-C bond forming reaction appears to involve the formation of an alkynyl rhenium species and subsequent nucleophilic attack of the alkynyl beta-carbon atom on the imine carbon to give a vinylidene rhenium species.
• Synthesis of 1-Boc-3-fluoroazetidine-3-carboxylic Acid
  作者：Eva Van Hende、Guido Verniest、Frederik Deroose、Jan-Willem Thuring、Gregor Macdonald、Norbert De Kimpe

  DOI：10.1021/jo802791r

  日期：2009.3.6

  Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.