TFA-Gly-OBn | 129990-27-8

• 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: TFA-Gly-OBn
• 英文别名: Benzyl 2-[(2,2,2-trifluoroacetyl)amino]acetate
• CAS: 129990-27-8
• 化学式: C₁₁H₁₀F₃NO₃
• 分子量: 261.201
• InChiKey: URIVBXAHLFEQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  TFA-Gly-OBn 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 benzyl 3-hexyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis of 2,3-Disubstituted Pyrroles Initiated by 1,4-Addition of Chelated Enolates onto Alkynyl Carbene Complexes

  摘要：

  Chelated glycine ester enolates, which have been found to be good nucleophiles, e.g., for Michael additions, undergo 1,4-addtition toward alkynyl Fischer carbene complexes. Instead of the expected unsaturated carbene amino acid derivatives, 2,3-disubstituted pyrroles are formed, probably by a domino process initiated by the 1,4-addition. Subsequent 1,3-H-shift, 1,2-addition, and reductive elimination during workup finalized the reaction cascade.

  DOI：

  10.1021/om4008136

文献信息

• A Straightforward Approach towards α-Amino-β-keto Esters via Acylation of Chelated Amino Acid Ester Enolates
  作者：Uli Kazmaier、Katharina Schultz、Laura Stief

  DOI：10.1055/s-0031-1289674

  日期：2012.2

  Chelated enolates were found to be good nucleophiles for reactions with acyl halides affording α-amino-β-keto esters. In most cases, the reactions are over after a few minutes and preparatively useful yields are obtained, independent of the protecting groups and halides used. Besides acyl halides, also the corresponding imidazolides can be used with similar success. With chloroformates as acylating

  发现螯合的烯醇化物是与提供α-氨基-β-酮酸酯的酰基卤反应的良好亲核试剂。在大多数情况下，反应在几分钟后结束并且获得制备有用的产率，而与所用的保护基团和卤化物无关。除了酰基卤之外，相应的咪唑啉也可以类似地成功使用。用氯甲酸酯作为酰化剂，可获得不同的被保护的氨基丙二酸酯。 酰化-酰基卤-氨基酸-氨基丙二酸酯-螯合的烯酸酯-酮
• Synthese α-<i>C</i>-glucosylierter α-Aminocarbonsäure-Derivate
  作者：Gerhard Simchen、Eckhardt Pürkner

  DOI：10.1055/s-1990-26928

  日期：——

  Synthesis of α-C-Glucosylated Derivatives of α-Amino Carboxylic Acids α-C-Glucosylation of amino acids was achieved by the reaction of ketene acetals 3 with the α-glucosyl bromide 4b in presence of zinc bromide to yield the β-anomers of the α-glucosyl-α-amino acid derivatives 6.

  α-C-糖苷化的α-氨基羧酸衍生物的合成通过将酮烯丙酮酸酯3与α-糖苷化溴化物4b在溴化锌存在下反应，实现了氨基酸的α-C-糖苷化，生成了α-糖苷化的α-氨基酸衍生物6的β-异构体。
• Stereoselective Formation of (E)-β-Alkoxy Acrylates from Fischer Carbene Complexes and Chelated Amino Acid Ester Enolates
  作者：Uli Kazmaier、Rupsha Chaudhuri

  DOI：10.1055/s-0033-1340496

  日期：——

  Chelated amino acid ester enolates react with alkyl Fischer carbene complexes via nucleophilic attack on the electrophilic carbene center. Subsequent elimination of the metal fragment and trifluoroacetamide results in the formation of β-alkoxy-α,β-­unsaturated esters in a highly E -stereoselective fashion.

  螯合氨基酸酯烯醇化物通过对亲电卡宾中心的亲核攻击与烷基 Fischer 卡宾配合物反应。随后金属片段和三氟乙酰胺的消除导致β-烷氧基-α,β-不饱和酯以高度E-立体选择性的方式形成。
• Allylic Alkylation versus Michael Induced Ring Closure:  Chelated Enolates as Versatile Nucleophiles
  作者：Matthias Pohlman、Uli Kazmaier、Thomas Lindner

  DOI：10.1021/jo049036q

  日期：2004.10.1

  Allylic carbonates 8 bearing an electron-withdrawing ester functionality can act as substrates for palladium-catalyzed allylic alkylations or as Michael acceptors with the option to undergo subsequent ring closure. Chelated amino acid ester enolates 1‘ are versatile nucleophiles for both reactions giving high yields and selectivites.

  带有吸电子酯官能度的烯丙基碳酸酯8可用作钯催化的烯丙基烷基化的底物或用作迈克尔受体，并可选择进行随后的闭环。螯合的氨基酸酯烯醇盐1 '是两种反应的通用亲核试剂，可提供高收率和选择性。