cis-1-benzoyl-2,3-diphenylaziridine | 13866-14-3

• 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: cis-1-benzoyl-2,3-diphenylaziridine
• 英文别名: cis-N-benzoyl-2,3-diphenylaziridine；[(2S,3R)-2,3-diphenylaziridin-1-yl]-phenylmethanone
• CAS: 13866-14-3
• 化学式: C₂₁H₁₇NO
• 分子量: 299.372
• InChiKey: UVYORQJDJXOKKJ-RLAPIPATSA-N

物化性质

• 熔点：
  138-141 °C
• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1-benzoyl-2,3-diphenylaziridine 在 三氯化铝 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 0.17h， 生成 1,1,2,2-四苯基乙烷
  参考文献：
  名称：

  一些 N-酰基氮丙啶的 Friedel-Crafts 反应：恶唑啉作为中间体

  摘要：

  3-取代的 1-酰基-2-苯基氮丙啶 1a、b 和 2b 出人意料地在苯中用 AlCl3 生成了 Friedel-Crafts 产物 3a、b 和 4b（酰化的 1-取代的 2,2-二苯乙胺），而无需加热，其中一些反应进一步到 1,1,2,2-四苯基乙烷 (5)。此外，还发现了恶唑啉 6a、b 和 7b。2,4,5-三苯基恶唑啉6b表明恶唑啉是3、4和5的中间体。讨论了这些特定恶唑啉不寻常的异裂开环。

  DOI：

  10.1002/ardp.19943270606
• 作为产物：
  描述：

  苯甲酰氯 、 cis-2,3-diphenylaziridine 以92%的产率得到cis-1-benzoyl-2,3-diphenylaziridine
  参考文献：
  名称：

  一些 N-酰基氮丙啶的 Friedel-Crafts 反应：恶唑啉作为中间体

  摘要：

  3-取代的 1-酰基-2-苯基氮丙啶 1a、b 和 2b 出人意料地在苯中用 AlCl3 生成了 Friedel-Crafts 产物 3a、b 和 4b（酰化的 1-取代的 2,2-二苯乙胺），而无需加热，其中一些反应进一步到 1,1,2,2-四苯基乙烷 (5)。此外，还发现了恶唑啉 6a、b 和 7b。2,4,5-三苯基恶唑啉6b表明恶唑啉是3、4和5的中间体。讨论了这些特定恶唑啉不寻常的异裂开环。

  DOI：

  10.1002/ardp.19943270606

文献信息

• Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines
  作者：Md Shafaat Al Mehedi、Jetze J. Tepe

  DOI：10.1021/acs.joc.9b00883

  日期：2019.6.7

  This work describes an extended version of the Corey–Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react

  这项工作描述了Corey-Chaykovsky反应的扩展版本，该反应使用硫代叶立德和稳定的酰基亚胺前体来获得恶唑啉。反应通过氮丙啶和恶唑啉的混合物进行，该混合物在用BF 3 ·OEt 2处理后原位Heine型氮丙啶环膨胀后提供反式恶唑啉。按照相同的一锅法，am酰亚胺与硫酰化物反应生成咪唑啉。
• Bifunctional Asymmetric Catalysis with Hydrogen Chloride: Enantioselective Ring Opening of Aziridines Catalyzed by a Phosphinothiourea
  作者：Eric Jacobsen、Tsuyoshi Mita

  DOI：10.1055/s-0029-1217344

  日期：——

  Ring-opening of aziridines with hydrogen chloride to form β-chloroamine derivatives is catalyzed by a chiral phosphinothiourea derivative in high yields and with high enantioselectivities. On the basis of (31)P NMR studies, activation of HCl appears to proceed via quantitative protonation of the catalyst to afford a phosphonium chloride complex.

  氮丙啶与氯化氢开环形成 β-氯胺衍生物是由手性膦硫脲衍生物以高产率和高对映选择性催化的。在 (31)P NMR 研究的基础上，HCl 的活化似乎是通过催化剂的定量质子化进行的，以提供氯化鏻络合物。
• Ring opening of aziridines by different fluorinating reagents: three synthetic routes to .alpha.,.beta.-fluoro amines with different stereochemical pathways
  作者：Gerard M. Alvernhe、Christine M. Ennakoua、Sylvie M. Lacombe、Andre J. Laurent

  DOI：10.1021/jo00337a024

  日期：1981.11
• Archier-Jay, Danielle; Besbes, Neji; Laurent, Andre, Bulletin de la Societe Chimique de France, 1989, # 44, p. 537 - 543
  作者：Archier-Jay, Danielle、Besbes, Neji、Laurent, Andre、Laurent, Eliane、Lesniak, Stanislaw、Tardivel, Robert

  DOI：——

  日期：——
• Single electron transfer versus nucleophilic ring opening in reactions of cis-trans pairs of activated 2-phenylaziridines. Strong influence of nitrogen pyramid for N-benzoylaziridines
  作者：Reinhard Falkenstein、Thomas Mall、Dieter Speth、Helmut Stamm

  DOI：10.1021/jo00078a014

  日期：1993.12

  Activated 2-phenylaziridines with a second substituent R in position 3 were made to react with xanthyl anion X-. Nucleophilic ring opening ia the only reaction that occurs with sulfonyl activation. The analogous N-benzoylaziridines 1 undergo this type of ring opening when the two substituents Ph and R are trans. The cis isomers (cis-1, Ph and R cis) react in this manner to a negligible extent if any. The (nearly) exclusive ring cleavage reaction of cis-1 is C-N homolysis of an intermediate ketyl formed by single electron transfer (SET) from X-. This cis-trans phenomenon is in accordance with the hypothesis that the two competing reactions depend in an opposite manner on the steepness of the nitrogen pyramid. A predominant or exclusive final result of SET is reductive aziridine opening and dimerization of the xanthyl radical X.. Formation of both diastereomers of the[GRAPHICS]amidoethylated xanthene in one case (R = Me) is evidence for a cross combination of X. with the radical formed by homolytic ring opening. Cross combination is also a likely path for R = H (no cis-trans isomerism), in addition to reductive ring opening. cis-Aziridines with dimethylcarbamoyl on nitrogen do not react via SET since the ketyl is not stabilized and therefore difficult to generate. Carbonyl attack on both types of acylaziridines competes more or less successfully with the two ring cleavage reactions.