trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine | 181874-01-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
• 英文别名: methyl (2R,3S)-2-methyl-1-[(S)-(4-methylphenyl)sulfinyl]-3-phenylaziridine-2-carboxylate
• CAS: 181874-01-1
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: WTMCSZYVWVBZTE-KLGBNGAQSA-N

物化性质

• 沸点：
  472.4±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以75%的产率得到methyl (2R,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  2-甲基ñ - （p -toluenesulfinyl）氮丙啶-2-羧酸：α甲基苯丙氨酸和α甲基-β-苯基丝氨酸的不对称合成

  摘要：

  由亚磺胺1经由Darzens型缩合反应制得的2-取代氮丙啶2a经过高度区域和立体控制的开环，以高对映体纯度得到α-甲基苯基丙氨酸和α-甲基-β-苯基丝氨酸。

  DOI：

  10.1016/0040-4039(96)01168-9
• 作为产物：
  描述：

  (S,E)-N-benzylidene-4-methylbenzenesulfinamide 、 lithium;(E)-2-bromo-1-methoxyprop-1-en-1-olate 以84%的产率得到trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
  参考文献：
  名称：

  Aziridine 2-carboxylate ester mediated asymmetric synthesis of α-alkyl β-amino acids

  摘要：

  The highly stereoselective ring opening of N-tosylaziridine 2-carboxylate esters with LiAlH4 followed by oxidation of the ensuing syn alcohols results in a highly efficient 4 step asymmetric synthesis of alpha-methyl beta-amino acids from N-sulfinylaziridine 2-carboxylate esters. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01095-2

文献信息

• Aza-Darzens Asymmetric Synthesis of <i>N</i>-(<i>p</i>-Toluenesulfinyl)aziridine 2-Carboxylate Esters from Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Hu Liu、Ping Zhou、Tianan Fang、G. Venkat Reddy、Yulian Zhang

  DOI：10.1021/jo990907j

  日期：1999.10.1

  The one-step aza-Darzens reaction of sulfinimines 2 with lithium alpha-bromoenolates readily affords diversely substituted cis and trans N-sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the alpha-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N-sulfinyl group in aziridines 3a and 3h with TFA/H2O affords VI-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.
• 2-Methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of α-methylphenylalanine and α-methyl-β-phenylserine
  作者：Franklin A. Davis、Hu Liu、G. Venkat Reddy

  DOI：10.1016/0040-4039(96)01168-9

  日期：1996.7

  2-Substituted aziridine 2a, prepared from sulfinimine 1 via a Darzens-type condensation, undergoes a highly regio- and stereocontrolled ring-opening to give α-methylphenylalanine and α-methyl-β-phenylserine in high enantiomeric purity.

  由亚磺胺1经由Darzens型缩合反应制得的2-取代氮丙啶2a经过高度区域和立体控制的开环，以高对映体纯度得到α-甲基苯基丙氨酸和α-甲基-β-苯基丝氨酸。
• Aziridine 2-carboxylate ester mediated asymmetric synthesis of α-alkyl β-amino acids
  作者：Franklin A. Davis、G.Venkat Reddy、Chang-Hsing Liang

  DOI：10.1016/s0040-4039(97)01095-2

  日期：1997.7

  The highly stereoselective ring opening of N-tosylaziridine 2-carboxylate esters with LiAlH4 followed by oxidation of the ensuing syn alcohols results in a highly efficient 4 step asymmetric synthesis of alpha-methyl beta-amino acids from N-sulfinylaziridine 2-carboxylate esters. (C) 1997 Elsevier Science Ltd.