(2S)-N-diphenylphosphinoyl-2-phenylmethylaziridine | 156301-20-1

• 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: (2S)-N-diphenylphosphinoyl-2-phenylmethylaziridine
• 英文别名: (2S)-2-benzyl-1-diphenylphosphorylaziridine
• CAS: 156301-20-1
• 化学式: C₂₁H₂₀NOP
• 分子量: 333.37
• InChiKey: SGBVUOBYGWIVKM-YDNXMHBPSA-N

物化性质

• 沸点：
  477.8±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-N-diphenylphosphinoyl-2-phenylmethylaziridine 在 magnesium 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 以68%的产率得到(S)-1-iodo-2-(diphenylphosphinamido)-3-phenylpropane
  参考文献：
  名称：

  N-二苯基亚膦酰基氮丙啶的制备及开环反应

  摘要：

  单手性N-二苯膦基氮丙啶可以由单手性2-氨基醇有效地制备。这样的氮丙啶与各种亲核试剂以良好的产率进行开环反应。脱膦酰基化是在温和的条件下完成的。

  DOI：

  10.1016/s0040-4020(97)10430-6
• 作为产物：
  描述：

  L-苯丙氨醇 在 四氢呋喃 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-N-diphenylphosphinoyl-2-phenylmethylaziridine
  参考文献：
  名称：

  利用二苯基次膦酸酯的核逸度直接从1,2-氨基醇制备N-二苯基膦酰基氮丙啶

  摘要：

  二苯基次膦酸酯阴离子的离去基团能力有助于改进N-二苯基膦酰基氮丙啶的制备

  DOI：

  10.1016/s0040-4039(00)76856-0

文献信息

• Synthesis of 2,5-Disubstituted 3-(Phenylsulfonyl)pyrrolidines via 5-<i>Endo</i>-Trig Cyclisation Reactions
  作者：Donald Craig、Philip Jones、Gareth Rowlands

  DOI：10.1055/s-1997-1054

  日期：——

  Reaction of lithiated (phenylsulfonyl)methane with enantiomerically pure N-diphenylphosphinylaziridines gives adducts 4, which may be acylated at the sulfone α-position by further lithiation and reaction with non-enolisable acid chlorides, giving ketones 5. Reduction followed by acetylation gives substrates 6, which undergo elimination and 5-endo-trig cyclisation to give 2,5-disubstituted 3-(phenylsulfonyl)pyrrolidines 7 in high yields and with excellent stereoselectivities. Some further reactions of the pyrrolidines are described.

  锂化（苯磺酰基）甲烷与对映体纯的 N-二苯基膦基氮丙啶反应生成加合物 4，通过进一步锂化并与不可烯醇化酰基氯反应，可将其在砜 α 位酰化，生成酮 5。还原后乙酰化生成底物6，经过消除和5-内三环化，以高产率和优异的立体选择性得到2,5-二取代的3-(苯磺酰基)吡咯烷7。描述了吡咯烷的一些进一步反应。
• A practical alternative to sulfonyl activation of aziridines: Ring-opening of N-diphenylphosphinoyl aziridines by carbon nucleophiles
  作者：Helen M.I. Osborn、J.B. Sweeney、William Howson

  DOI：10.1016/s0040-4039(00)77020-1

  日期：1994.4

  The ring-opening reaction of N-diphenylphosphinoylaziridines by Copper (1)-modified Grignard reagents proceeds in good to excellent yield and with complete regiospecificity.
• Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
  作者：Maité Sylla-Iyarreta Veitía、Pierre Louis Brun、Pierre Jorda、Annie Falguières、Clotilde Ferroud

  DOI：10.1016/j.tetasy.2009.07.045

  日期：2009.9

  Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected beta(3)-amino nitriles into their corresponding N-protected beta(3)-amino acids.The biotransformations were obtained in different proportions depending oil the nitrilase involved The best hydrolysis results were achieved for the N-Cbz-beta(3)-amino nitrile from i-alanine using the NIT-107, in a phosphate buffer at 0 05 M However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide beta(3)-amino nitriles. Two simple and efficient procedures to prepare the beta(3)-amino nitriles from their analogous alpha-amino acids are described Thirty four new substances were synthesized and characterized over the course of this work. (C) 2009 Elsevier Ltd All rights reserved
• Chiral 1,3-diamines from a lithiated isocyanide and chiral aziridines
  作者：Alexander Kaiser、Miriam Balbi

  DOI：10.1016/s0957-4166(99)00075-0

  日期：1999.3

  Reaction of lithiated 4-methoxybenzylisocyanide with homochiral amino acid derived N-tosyl- and N-diphenylphosphinoylaziridines proceeds diastereoselectively to provide N-protected 3-isocyanoamines. Separation of the diastereomers of these adducts or the corresponding formamides, and subsequent transformations, lead to 1,3-diamines and their monoprotected and differentially bisprotected derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Osborn Helen M. I., Cantrill Alex A., Sweeney J. B., Howson William, Tetrahedron Lett, 35 (1994) N 19, S 3159-3162
  作者：Osborn Helen M. I., Cantrill Alex A., Sweeney J. B., Howson William

  DOI：——

  日期：——