(2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-cyclohexylaziridine | 1072879-35-6

• 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: (2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-cyclohexylaziridine
• 英文别名: ethyl (2R,3R)-1-[bis(3,5-ditert-butyl-4-methoxyphenyl)methyl]-3-cyclohexylaziridine-2-carboxylate
• CAS: 1072879-35-6
• 化学式: C₄₂H₆₅NO₄
• 分子量: 647.982
• InChiKey: DQXQSVTYMKSZLN-CDTKNAPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  重氮乙酸乙酯 、 N-cyclohexylmethylidene-bis(4-methoxy-3,5-di-tert-butylphenyl)methylamine 在 三苯基硼酸酯 、 (R)-2,2'-二苯基-3,3'-(4-联菲酚) 作用下， 以 甲苯 为溶剂， 反应 24.08h， 生成 (2R,3R)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-cyclohexylaziridine 、 (2S,3S)-cis-1-(N-1-bis(4-methoxy-3,5-di-tert-butylphenyl)methyl)-2-carboxyethyl-3-cyclohexylaziridine
  参考文献：
  名称：

  Mapping the Active Site in a Chemzyme: Diversity in the N-Substituent in the Catalytic Asymmetric Aziridination of Imines

  摘要：

  The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.

  DOI：

  10.1021/ol802431v

文献信息

• Mapping the Active Site in a Chemzyme: Diversity in the <i>N</i>-Substituent in the Catalytic Asymmetric Aziridination of Imines
  作者：Yu Zhang、Zhenjie Lu、Aman Desai、William D. Wulff

  DOI：10.1021/ol802431v

  日期：2008.12.4

  The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.