(R)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionic acid ethyl ester
• 英文别名: (2R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(5-iodo-indol-3-yl)propionate；ethyl (R)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionate；ethyl 3,3,3-trifluoro-2-hydroxy-2-(5-iodo-indol-3-yl)propanoate；ethyl (2R)-3,3,3-trifluoro-2-hydroxy-2-(5-iodo-1H-indol-3-yl)propanoate
• 化学式: C₁₃H₁₁F₃INO₃
• 分子量: 413.135
• InChiKey: BEDWMXUFZPWAOL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-碘吲哚 、 3,3,3-三氟丙酮酸乙酯 在 辛可宁 作用下， 以 乙醚 为溶剂， 生成 (R)-3,3,3-trifluoro-2-hydroxy-2-(5-iodoindol-3-yl)propionic acid ethyl ester
  参考文献：
  名称：

  Effect of chirality of small molecule organofluorine inhibitors of amyloid self-assembly on inhibitor potency

  摘要：

  The effect of enantiomeric trifluoromethyl-indolyl-acetic acid ethyl esters on the fibrillogenesis of Alzheimer's amyloid beta (A beta) peptide is described. These compounds have been previously identified as effective inhibitors of the A beta self-assembly in their racemic form. Thioflavin-T Fluorescence Spectroscopy and Atomic Force Microscopy were applied to assess the potency of the chiral target compounds. Both enantiomers showed significant inhibition in the in vitro assays. The potency of the enantiomeric inhibitors appeared to be very similar to each other suggesting the lack of the stereospecific binding interactions between these small molecule inhibitors and the A beta peptide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.066

文献信息

• Novel Enantiocomplementary<i>C</i>₂‐Symmetric Chiral Bis(imidazoline) Ligands: Highly Enantioselective Friedel–Crafts Alkylation of Indoles with Ethyl 3,3,3‐Trifluoropyruvate
  作者：Shuichi Nakamura、Kengo Hyodo、Yuko Nakamura、Norio Shibata、Takeshi Toru

  DOI：10.1002/adsc.200800189

  日期：2008.7.7

  Enantioselective Friedel–Crafts alkylations of a variety of indoles with ethyl 3,3,3-trifluoropyruvate catalyzed by novel chiral m-phenylenebis(imidazoline)-copper(II) complexes or the bis(imidazoline)-achiral acid combination afforded products with high enantioselectivity. Both enantiomers of indole derivatives can be prepared with high enantioselectivities by tuning the N-substituents of the imidazoline

  的各种吲哚的对映选择性的Friedel-Crafts烷基化反应与由新型手性催化乙基3,3,3-三氟丙酮米-phenylenebis（咪唑啉） -铜（II）配合物或双（咪唑啉）-achiral酸组合得到的产品具有高对映选择性。吲哚衍生物的两种对映异构体可以通过调节咪唑啉的N-取代基而以高对映选择性制备。
• Asymmetric Calcium Catalysis: Highly Enantioselective Carbonyl-Ene and Friedel-Crafts Reactions for the Synthesis of Quaternary α-Hydroxy Esters Bearing a Trifluoromethyl Group
  作者：Magnus Rueping、Teerawut Bootwicha、Supakeat Kambutong、Erli Sugiono

  DOI：10.1002/asia.201200063

  日期：2012.6

  Enantioselective calcium‐catalyzed addition reactions of styrene and indole derivatives with trifluoropyruvates have been developed. The alkaline‐earth metal‐catalyzed reactions proceed smoothly to afford the corresponding products in high yields and with good to excellent enantioselectivities under mild reaction conditions.

  已经开发了苯乙烯和吲哚衍生物与三氟丙酮酸盐的对映选择性钙催化加成反应。在温和的反应条件下，碱土金属催化的反应可顺利进行，从而以高收率提供良好的对映选择性，得到相应的产物。
• Enantioselective Friedel-Crafts alkylation of indoles with trifluoropyruvates catalyzed by chiral Cu(II) complex bearing binaphthyl-proline hybrid ligands
  作者：Chao Yao、Jiaqi Hou、Qihang Cai、Yaoqi Chen、Chao Wang、Jiemian Liang、Zilin Jiao、Lin Li、Yue-Ming Li

  DOI：10.1016/j.tet.2024.133874

  日期：2024.3

  A mild and efficient catalyst system for asymmetric Friedel-Crafts alkylation of indoles with trifluoropyruvates was reported. The chiral ligands took the advantages of both the proline and the binaphthyl moieties, and the in situ prepared Cu(II) catalyst showed good substrate tolerance in the reactions. Indoles bearing different substituents could be tolerated, and the desired products could be obtained

  报道了一种温和高效的催化剂体系，用于吲哚与三氟丙酮酸酯的不对称弗里德尔-克来福特烷基化。手性配体同时具有脯氨酸和联萘基的优点，原位制备的Cu(II)催化剂在反应中表现出良好的底物耐受性。可以耐受带有不同取代基的吲哚，并且可以以高达99%的产率和高达98%的ee得到所需的产物。特别是，反应可以在克级进行，且不损失立体选择性，部分产物在简单结晶后即可达到99% ee。
• Highly Enantioselective Organocatalytic Hydroxyalkylation of Indoles with Ethyl Trifluoropyruvate
  作者：Béla Török、Mohammed Abid、Gábor London、Joseph Esquibel、Marianna Török、Shilpa C. Mhadgut、Ping Yan、G. K. Surya Prakash

  DOI：10.1002/anie.200462877

  日期：2005.5.13