(E)-N-([1,1'-biphenyl]-4-ylmethylene)-P,P-diphenylphosphinic amide | 338741-85-8

• 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-([1,1'-biphenyl]-4-ylmethylene)-P,P-diphenylphosphinic amide
• 英文别名: N-(4-biphenylmethylene)-P,P-diphenylphosphinic amide；(E)-N-diphenylphosphoryl-1-(4-phenylphenyl)methanimine
• CAS: 338741-85-8
• 化学式: C₂₅H₂₀NOP
• 分子量: 381.414
• InChiKey: ROIPEITVQVDYGY-LHLOQNFPSA-N

物化性质

• 沸点：
  550.1±43.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-丁二烯酸乙酯 、 (E)-N-([1,1'-biphenyl]-4-ylmethylene)-P,P-diphenylphosphinic amide 在 chiral bifunctional thiourea catalyst 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 48.42h， 以81%的产率得到ethyl (2S)-2-(biphenyl-4-yl)-1-(diphenylphosphoryl)-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions

  摘要：

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.

  DOI：

  10.1021/ja801344w
• 作为产物：
  描述：

  对苯基苯甲醛 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (E)-N-([1,1'-biphenyl]-4-ylmethylene)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  使用基于四氢噻吩的手性硫化物作为有机催化剂对二芳基氮丙啶的对映选择性合成。

  摘要：

  这项工作描述了使用（thiolan-2-yl）diarylmethanol苄基醚作为有机催化剂通过亚氨基Corey-Chaykovsky反应进行的苄基溴和亚胺的催化和不对称叠氮化（15例，95-98％ee）。通过快速有效的合成途径制备催化剂及其类似物，所述合成途径以双亲核取代和Shi环氧化为关键步骤。

  DOI：

  10.1039/c3cc47550f

文献信息

• Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene-based chiral sulfides as organocatalysts
  作者：Meng-Ting Huang、Hsin-Yi Wu、Rong-Jie Chein

  DOI：10.1039/c3cc47550f

  日期：——

  This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps

  这项工作描述了使用（thiolan-2-yl）diarylmethanol苄基醚作为有机催化剂通过亚氨基Corey-Chaykovsky反应进行的苄基溴和亚胺的催化和不对称叠氮化（15例，95-98％ee）。通过快速有效的合成途径制备催化剂及其类似物，所述合成途径以双亲核取代和Shi环氧化为关键步骤。
• Enantioselective Borodeuteride Reduction of Aldimines Catalyzed by Cobalt Complexes:  Preparation of Optically Active Deuterated Primary Amines
  作者：Daichi Miyazaki、Kohei Nomura、Tatsuya Yamashita、Izumi Iwakura、Taketo Ikeno、Tohru Yamada

  DOI：10.1021/ol0349920

  日期：2003.10.1

  [reaction: see text] The enantioselective borodeuteride reduction catalyzed by optically active beta-ketoiminato cobalt complexes was applied to N-(di(o-tolyl)phosphinyl)aldimines to afford the corresponding optically active deuterated primary amines in high yields with high enantiomeric excesses after simple deprotection. The present deuteride reduction of aldimines is in the opposite sense of the enantioselective

  [反应：见正文]将旋光性β-酮亚氨基钴配合物催化的对映选择性硼氘化物还原反应应用于N-（二（邻（甲苯基）次膦基）亚丙基胺），以高收率和高对映体过量获得相应的旋光氘代伯胺。简单的脱保护后。对于先前报道的酮或二苯基次膦基醛亚胺的硼氢化物还原，本发明的醛亚胺的氘代还原与对映选择性相反。讨论了这些对映选择性还原中的立体化学过程。
• Asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines
  作者：Pedro Pinho、Pher G Andersson

  DOI：10.1016/s0040-4020(00)01142-x

  日期：2001.2

  The addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines is a convenient method for the preparation of optically enriched amines. Herein we present our most recent results on this reaction, including solvent effects on the enantioselectivity and the extension of this method to a variety of N-(diphenylphosphinoyl) imines. (C) 2001 Elsevier Science Ltd. All rights reserved.
• (Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine
  作者：Shang-Hua Wang、Rong-Jie Chein

  DOI：10.1016/j.tet.2014.12.063

  日期：2016.5

  A dual catalyst system using THT-based chiral sulfide 2a and H-bond donor 10a was developed for the asymmetric imino Corey-Chaykovsky reaction. Under the optimum reaction conditions, cinnamyl bromide reacted with a wide scope of N-diphenylphosphinic aldimines, to give the major trans-aryl cinnamyl aziridines with up to 98% ee. The role of H-bond donor 10a was demonstrated empirically as well. (C) 2014 Elsevier Ltd. All rights reserved.
• Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions
  作者：Yuan-Qing Fang、Eric N. Jacobsen

  DOI：10.1021/ja801344w

  日期：2008.4.1

  A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.