乙烯胺,N-(三苯基正膦亚基)- | 121198-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙烯胺,N-(三苯基正膦亚基)-
• 英文名称: 1,1,1-triphenyl-2-aza-1λ⁵-phosphabuta-1,3-diene
• 英文别名: triphenyl(vinyliminoi)phosphorane；(vinylimino)triphenylphosphorane；N-Vinyliminotriphenylphosphorane；triphenyl(vinylimino)phosphorane；Ethenamine, N-(triphenylphosphoranylidene)-；ethenylimino(triphenyl)-λ5-phosphane
• CAS: 121198-57-0
• 化学式: C₂₀H₁₈NP
• 分子量: 303.343
• InChiKey: CLQQBIWQYMJWDE-UHFFFAOYSA-N

物化性质

• 熔点：
  90 °C (decomp)
• 沸点：
  439.2±28.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  乙烯胺,N-(三苯基正膦亚基)- 、 丁烯酮 以 苯 为溶剂， 反应 24.0h， 以25%的产率得到碳酸甲丙酯
  参考文献：
  名称：

  新型N-乙烯基-、N-(1-丁基乙烯基)-和N-(1-甲基-1-戊烯基)亚氨基三苯基膦的制备及其与α,β-不饱和酮的反应

  摘要：

  新型 N-乙烯基-(2a) 以及 N-(1-丁基乙烯基)-(2b) 和 N-(1-甲基-1-戊烯基) 亚氨基三苯基膦 (2c) 的混合物是通过叠氮乙烯和 2-叠氮基-1-己烯分别与三苯基膦。2a、2b 和 2c 与 α,β-不饱和酮的热反应经历烯胺型烷基化和随后的氮杂-维蒂希反应，以中等产率得到吡啶衍生物。

  DOI：

  10.1246/bcsj.61.2235
• 作为产物：
  描述：

  1-(Benzotriazol-1-yl)ethylimino-triphenyl-lambda5-phosphane 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 2.0h， 生成 乙烯胺,N-(三苯基正膦亚基)-
  参考文献：
  名称：

  A New and Safe Approach to (N-Vinylimino)phosphoranes

  摘要：

  1-[alpha-(Phosphoranylideneamino)alkyl] benzotriazoles, obtained by Staudinger phosphenimide-forming reaction of (azidoalkyl)benzotriazoles, possessing a proton in a beta-position to nitrogen reacted with sodium hydride in THF to afford (N-vinylimino)phosphoranes in high yields. The latter were trapped with chalcone to give the corresponding 2,4-diphenylpyridines.

  DOI：

  10.1021/jo00089a017

文献信息

• On the Reaction of (Vinylimino)phosphoranes. Part 17. Preparation of<i>N</i>-Vinylcarbodiimides and Their [4+2] Cycloaddition with Several Dienophiles to Give Pyridine Ring System
  作者：Makoto Nitta、Hironobu Soeda、Shinya Koyama、Yukio Iino

  DOI：10.1246/bcsj.64.1325

  日期：1991.4

  derivatives was examined to give N-phenyl-N′-vinylcarbodiimide and its derivatives, all of which underwent a [4+2] cycloaddition reaction with electron-rich dienophiles (enamines) and/or electron-deficient dienophiles (activated acetylenes), resulting in the formation of a pyridine ring system. The regioselectivity of the cycloaddition reaction could be rationalized on the basis of a frontier orbital

  研究了（乙烯基亚氨基）三苯基正膦及其几种衍生物的氮杂-维蒂希反应，得到了 N-苯基-N'-乙烯基碳二亚胺及其衍生物，所有这些都与富电子亲二烯体（烯胺）发生了 [4+2] 环加成反应和/或缺电子的亲二烯体（活化的乙炔），导致形成吡啶环系统。环加成反应的区域选择性可以在前沿轨道考虑的基础上合理化。
• On the reactions of (vinylimino)phosphoranes and related compounds. Part 30. Short new synthesis of 5-azaazulene derivatives. Some comments on reactivities of (vinylimino)phosphoranes
  作者：Makoto Nitta、Yukio Iino、Satoshi Mori、Tohru Takayasu

  DOI：10.1039/p19950001001

  日期：——

  A short new synthesis of phenyl-substituted and annulated 5-azaazulene (cyclopenta[c]azepine) derivatives 15–18 consists of the reaction of [(1-phenylvinyl)imino]- and benz-annulated [(cycloalkenyl)imino]-phosphoranes 8–11 with 5-(dimethylaminomethylene)cyclopenta-1,3-dienecarbaldehyde 1 in an enamine alkylation (Michael addition) process, subsequent proton migration–ketonization, and condensation

  苯基取代的和环化5- azaazulene（环戊二烯并[的简短新合成Ç ]氮杂）衍生物15 - 18由[（1-苯基乙烯基）亚氨基]的反应的-和苯并-环[（环烯基）亚氨基] -phosphoranes 8 - 11 5-（二甲氨基亚甲基）环戊二烯基-1,3- dienecarbaldehyde 1中的烯胺烷基化与所述膦亚胺部分（氮杂Wittig反应）的甲酰基的（迈克尔加成）处理，随后的质子迁移酮化，并冷凝。在另一方面，醛的反应1与（vinylimino）正膦12 - 14，其具有在相对于氮原子的α位没有苯基，由一个分子内氮杂Wittig反应或醛的取代反应的1与正膦12 - 14和随后水解，得到5-（氨基亚甲基）环戊二烯-1- ，3-二烯甲醛19及其衍生物20和21。在选择性的上下文中膦的反应观察到的8 - 11和12 - 14用醛1，分别对化合物MNDO计算1和12A，12B以及在模型化合物8C
• Nitta, Makoto; Iino, Yukio; Hara, Eijiro, Journal of the Chemical Society. Perkin transactions I, 1989, p. 51 - 56
  作者：Nitta, Makoto、Iino, Yukio、Hara, Eijiro、Kobayashi, Tomoshige

  DOI：——

  日期：——
• On the reaction of (vinylimino)phosphorane and related compounds. 22. Syntheses and structural studies of methanocycloundeca[b]pyrrole ring systems
  作者：Nobuhiro Kanomata、Kenichi Kamae、Yukio Iino、Makoto Nitta

  DOI：10.1021/jo00046a010

  日期：1992.9

  Novel 2-phenyl-6,11- and 2-phenyl-4,9-methanocycloundeca[b]pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3,8-methano[11]annulenone (3), a 10pi-electron vinylogue of tropone, with [(l-phenylvinyl)imino]triphenylphosphorane (8a) and subsequent dehydrogenation. Similarly, the reaction of the annulenone 3 with (inden-3-ylimino)tributylphosphorane (8c) and subsequent aromatization afforded 7,12- and 9,14-methano-15H-cycloundeca[b]indeno[2,3-d]pyrroles (15c and 16c), which also have methanocycloundeca[b]pyrrole ring systems. Preparation of 2-phenyl-5,10-methanocycloundeca[b]pyrrole (17), an isomer of both 15a and 16a, was also accomplished in low yield by the reaction of 4,9-methano[ll]annulenone (5) with an excess of [(1-phenylvinyl)imino]tributylphosphorane (8d). The reactivity of annulenone 5 with (vinylimino)phosphoranes was found to be quite low as compared to the higher reactivity of annulenone 3 and tropone. Compounds 15a,c, 16a,c, and 17 are the first nitrogen analogues of cyclopentacycloundecene ring systems which have vinylogous structures of 1-azaazulene. Structures of the products obtained were examined by H-1 NMR spectra and UV spectra. The H-1 NMR spectra clarified that the compounds 15a,c, 16a,c, and 17 are aromatic molecules having a diatropic 14pi-electron system, and 5,10-methano derivative 17 has a more diatropic nature than the compounds 15a,c and 16a,c. The UV spectra of 15a,c, 16a,c, and 17 exhibited increased cyclic conjugation of the aromatic perimeter according to a bathochromic shift of the longest absorption maxima as compared to the corresponding 1-azaazulene derivatives.
• [4+2] Cycloaddition Reactions of Neutral 2-Azadienes with Electron-deficient Dienophiles
  作者：Francisco Palacios、Concepción Alonso、Gloria Rubiales、Cristina Tobillas、José María Ezpeleta

  DOI：10.3987/com-03-s65

  日期：——

  A method for the preparation of functionalized tetrahydropyridine and triazine derivatives is described, based on aza Diels-Alder reaction of neutral 2-aza-1,3-dienes with electron-poor dienophiles as tetracyanoethylene and N-phenyl-1,2,4-triazoline-3,5-dione.