ethyl (2S)-4-(3,5-bis-trifluoromethyl-phenyl)-2-(2-methyl-prop-2-yl-(S)-sulfinylamino)-pent-4-enoate

• 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: ethyl (2S)-4-(3,5-bis-trifluoromethyl-phenyl)-2-(2-methyl-prop-2-yl-(S)-sulfinylamino)-pent-4-enoate
• 英文别名: ethyl 2S,4S-(3,5-bis-trifluoromethyl-phenyl)-2-(2-methyl-propane-2-sulfinylamino)-pent-4-enoate；ethyl (2S)-4-[3,5-bis(trifluoromethyl)phenyl]-2-[[(S)-tert-butylsulfinyl]amino]pent-4-enoate
• 化学式: C₁₉H₂₃F₆NO₃S
• 分子量: 459.453
• InChiKey: MNPILWMJKOJABY-JGVYIQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-4-(3,5-bis-trifluoromethyl-phenyl)-2-(2-methyl-prop-2-yl-(S)-sulfinylamino)-pent-4-enoate 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 6.0h， 以89%的产率得到(S)-2-amino-4-(3,5-bis-trifluoromethyl-phenyl)-pent-4-enoic acid
  参考文献：
  名称：

  Enantioselective synthesis of non-proteinogenic 2-arylallyl-α-amino acids via Pd/In catalytic cascades

  摘要：

  An efficient synthesis of both R- and S-enantiomers of 2-arylallyl-alpha-amino acids via a diastereoselective Pd/In mediated catalytic allylation of chiral N-sulfinyl-alpha-imino esters is described. The potential for further enhancement of molecular complexity and creating contiguous chiral centres by interfacing these processes with catalytic cyclisation-anion capture methodology is demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.098
• 作为产物：
  描述：

  (S,E)-ethyl 2-[(tert-butylsulfinyl)imino]acetate 、 丙二烯 、 3,5-双(三氟甲基)碘苯 在 palladium diacetate 、 indium 哌啶 、 copper(l) iodide 、 三(2-呋喃基)膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、50.0 kPa 条件下， 反应 24.0h， 以69%的产率得到ethyl (2S)-4-(3,5-bis-trifluoromethyl-phenyl)-2-(2-methyl-prop-2-yl-(S)-sulfinylamino)-pent-4-enoate
  参考文献：
  名称：

  Enantioselective synthesis of non-proteinogenic 2-arylallyl-α-amino acids via Pd/In catalytic cascades

  摘要：

  An efficient synthesis of both R- and S-enantiomers of 2-arylallyl-alpha-amino acids via a diastereoselective Pd/In mediated catalytic allylation of chiral N-sulfinyl-alpha-imino esters is described. The potential for further enhancement of molecular complexity and creating contiguous chiral centres by interfacing these processes with catalytic cyclisation-anion capture methodology is demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.098

文献信息

• Enantioselective synthesis of non-proteinogenic 2-arylallyl-α-amino acids via Pd/In catalytic cascades
  作者：Ronald Grigg、Shaun McCaffrey、Visuvanathar Sridharan、Colin W.G. Fishwick、Colin Kilner、Stewart Korn、Kevin Bailey、John Blacker

  DOI：10.1016/j.tet.2006.09.098

  日期：2006.12

  An efficient synthesis of both R- and S-enantiomers of 2-arylallyl-alpha-amino acids via a diastereoselective Pd/In mediated catalytic allylation of chiral N-sulfinyl-alpha-imino esters is described. The potential for further enhancement of molecular complexity and creating contiguous chiral centres by interfacing these processes with catalytic cyclisation-anion capture methodology is demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.