trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine | 181874-04-4

• 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: trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
• 英文别名: (2R,3S)-N-(p-toluenesulfonyl)-2-carbomethoxy-2-methyl-3-phenylaziridine；methyl (2R,3S)-2-methyl-1-(4-methylphenyl)sulfonyl-3-phenylaziridine-2-carboxylate
• CAS: 181874-04-4
• 化学式: C₁₈H₁₉NO₄S
• 分子量: 345.419
• InChiKey: AIYLUDGDLPOMDO-CXEJCQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 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：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine 在 palladium hydroxide - carbon 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,3S)-2,3-Dimethylphenylalanine methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted α-Amino Acids Using 2H-Azirine-2-carboxylate Esters. Synthesis of 3,3-Disubstituted Aziridine-2-carboxylate Esters

  摘要：

  DOI：

  10.1021/jo9702610
• 作为产物：
  描述：

  (S,E)-N-benzylidene-4-methylbenzenesulfinamide 在 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 反应 1.5h， 生成 trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
  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

文献信息

• Asymmetric Synthesis of 2<i>H</i>-Azirine 2-Carboxylate Esters
  作者：Franklin A. Davis、Hu Liu、Chang-Hsing Liang、G. Venkat Reddy、Yulian Zhang、Tianan Fang、Donald D. Titus

  DOI：10.1021/jo991389f

  日期：1999.11.1

  sulfenic acid (RSOH) from nonracemic N-sulfinylaziridine 2-carboxylate esters (4). Optimum yields were obtained when the aziridine was treated with TMSCl at -95 degrees C followed by LDA, which was attributed to the improved leaving group ability of an silicon-oxonium species. By using this new methodology the first asymmetric syntheses of the marine cytotoxic antibiotics (R)-(-)- and (S)-(+)-dysidazirine

  最小的不饱和氮杂环2H-Azirine 2-羧酸酯（5）可通过从非外消旋N-亚磺酰基氮丙啶2​​-羧酸酯（4）中碱诱导的亚磺酸（RSOH）的消除，轻松制备成对映体纯形式。当在-95℃下用TMCSI随后用LDA对氮丙啶进行处理时，可获得最佳产率，这归因于硅-氧鎓物种的离去基团能力提高。通过使用这种新方法，完成了海洋细胞毒性抗生素（R）-（-）-和（S）-（+）-dysidazirine（2）的第一个不对称合成。
• 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.
• 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.
• Asymmetric Synthesis of β-Substituted α-Amino Acids Using 2<i>H</i>-Azirine-2-carboxylate Esters. Synthesis of 3,3-Disubstituted Aziridine-2-carboxylate Esters
  作者：Franklin A. Davis、Chang-Hsing Liang、Hu Liu

  DOI：10.1021/jo9702610

  日期：1997.6.13