4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate | 685842-45-9

• 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: 4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate
• CAS: 685842-45-9
• 化学式: C₁₈H₂₄F₃NO₅S
• 分子量: 423.453
• InChiKey: NHBSKSQQMPEZTF-YMGMXPECSA-N

物化性质

• 沸点：
  490.7±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-2-Amino-2-trifluoromethyl-succinic acid 1-ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-α-trifluoromethyl aspartic acid via titanium enolate addition to a sulfinimine of trifluoropyruvate

  摘要：

  The reaction of an enantiomerically pure sulfinimine of trifluoropyruvate with several metal enolates is described. The use of TiCl(O-iPr)(3)/LDA produced the corresponding sulfinamides with high stereocontrol. The latter could be smoothly transformed into each enantiomer of alpha-trifluoromethyl aspartic acid with high ee, which has been previously synthesized only in racemic form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.013
• 作为产物：
  描述：

  醋酸叔丁酯 、 3,3,3-Trifluoro-2-[(E)-(R)-toluene-4-sulfinylimino]-propionic acid ethyl ester 在 lithium diisopropyl amide 、 三异丙氧基氯化钛 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate 、 4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate 、 4-tert-butyl 1-ethyl N-[(4-methylphenyl)sulfinyl]-2-(trifluoromethyl)aspartate
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-α-trifluoromethyl aspartic acid via titanium enolate addition to a sulfinimine of trifluoropyruvate

  摘要：

  The reaction of an enantiomerically pure sulfinimine of trifluoropyruvate with several metal enolates is described. The use of TiCl(O-iPr)(3)/LDA produced the corresponding sulfinamides with high stereocontrol. The latter could be smoothly transformed into each enantiomer of alpha-trifluoromethyl aspartic acid with high ee, which has been previously synthesized only in racemic form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.013