(2S,3S)-3-methylaziridin-2-yl(diphenyl)methanol | 167226-25-7

• 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,3S)-3-methylaziridin-2-yl(diphenyl)methanol
• 英文别名: [(2S,3S)-3-methylaziridin-2-yl]-diphenylmethanol
• CAS: 167226-25-7
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: XYONBPTWXJCFNC-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-methylaziridin-2-yl(diphenyl)methanol 在 六甲基磷酰三胺 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (1'S,2''R)-tert-butyl 1'-(3'',3''-diphenyloxiran-2''-yl)ethylcarbamate
  参考文献：
  名称：

  Aza-Payne rearrangement of α,α-disubstituted-aziridinemethanols

  摘要：

  The aza-Payne rearrangement of activated N-Ts-alpha,alpha-disubstituted-aziridinemethanols, induced by NaOH in the mixed solvent (BuOH)-Bu-t/H2O/THF (4:5:1) or NaH in a mixed solvent of THF/HMPA (10: 1), as well as some N-Boc-alpha,alpha-disubstituted-aziridinemethanols with the latter reagent/solvent combination, provides the corresponding epoxides in up to 99% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.035
• 作为产物：
  描述：

  (+)-(2S,3S)-1-trityl-3-methylaziridin-2-yl(diphenyl)methanol 在 硫酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S,3S)-3-methylaziridin-2-yl(diphenyl)methanol
  参考文献：
  名称：

  使用衍生自氮丙啶甲醇的手性恶唑硼烷定型化合物还原不对称酮

  摘要：

  使用衍生自氮丙啶-2-叔丁醇1和2的1,3,2-恶唑硼烷进行的对苯乙酮的不对称硼烷还原可以高光学收率得到相应的醇。描述了使用D-和L-丝氨酸以及D-和L-苏氨酸作为起始原料的新型手性催化剂1和2的合成。

  DOI：

  10.1016/0040-4039(94)02313-z

文献信息

• The Influence of Substituents on the Hydroxyl-Bearing Carbon in the Aza-Payne Rearrangement of Aziridinemethanols
  作者：Wenjin Xu、Jun Zhang、Hao Guo、Qifeng Zhu、Xianming Hu

  DOI：10.2174/157017809788681310

  日期：2009.7.1

  A new series of α,α-disubstituted aziridinemethanols have been synthesized and their aza-Payne rearrangement reactions were studied. The results show that α,α-disubstituted aziridinemethanols with electron-withdrawing groups accelerate the aza-Payne rearrangement than those with electron-donating groups. All of the rearrangements proceeded through an inversion of configuration at the C-2 carbon.

  合成了一系列新的α，α-二取代氮丙啶甲醇，并对其氮杂-Payne重排反应进行了研究。结果表明，具有吸电子基团的α，α-二取代氮丙啶甲醇比具有供电子基团的α-α-二取代氮丙啶重排更容易。所有的重排都是通过C-2碳原子的构型反转进行的。
• Aziridin-2-yl methanols as organocatalysts in Diels–Alder reactions and Friedel–Crafts alkylations of N-methyl-pyrrole and N-methyl-indole
  作者：Bianca F. Bonini、Elena Capitò、Mauro Comes-Franchini、Mariafrancesca Fochi、Alfredo Ricci、Binne Zwanenburg

  DOI：10.1016/j.tetasy.2006.11.028

  日期：2006.11

  A series of enantiomerically pure aziridin-2-yl methanols have been synthesized from aziridine-2-carboxylic esters and have been tested as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole using alpha,beta-unsaturated aldehydes. Moderate to good ee's have been obtained. The coupling of N-methyl-pyrrole with crotonaldehyde and cinnamaldehyde using (2S,3S)-3-methylazirin-2-yl(diphenyl)methanol TFA salt as the catalyst gave the best results (ee 75%). (c) 2006 Elsevier Ltd. All rights reserved.