ethyl (R)-4-(1H-indol-3-yl)-2-oxo-4-phenylbutanoate | 1201664-92-7

• 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: ethyl (R)-4-(1H-indol-3-yl)-2-oxo-4-phenylbutanoate
• 英文别名: 4-(1H-indol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester；4-(1H-indol-3-yl)-2-oxo-4-phenylbutyric acid ethyl ester；ethyl 4-(1H-indol-3-yl)-2-oxo-4-phenylbutanoate；ethyl (4R)-4-(1H-indol-3-yl)-2-oxo-4-phenylbutanoate
• CAS: 1201664-92-7
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: LQEGMBKZYMKBFO-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 4-(1H-indol-3-yl)-2-oxo-4-phenylbut-3-enoate 在 二氢吡啶 、 C₄₄H₁₉F₁₀O₄P 作用下， 以 二氯甲烷 为溶剂， 以64 %的产率得到ethyl (R)-4-(1H-indol-3-yl)-2-oxo-4-phenylbutanoate
  参考文献：
  名称：

  不对称二元酸催化：对映选择性共轭氢化物还原中的可切换对映选择性

  摘要：

  金属离子从 Zr(IV) 到 Fe(III) 的交换导致二元酸催化的共轭氢化物还原的对映选择性发生变化。在 Hantzsch 酯存在下，γ-吲哚基 β,γ-不饱和 α-酮酯可以分别还原为所需的 ( S )- 或 ( R )- 产物，具有良好至优异的对映选择性（高达 98% ee） .

  DOI：

  10.1021/acs.orglett.2c04087

文献信息

• Optically Active 1,1′-Spirobiindane-7,7′-diol (SPINOL)-Based Phosphoric Acids as Highly Enantioselective Catalysts for Asymmetric Organocatalysis
  作者：Chun-Hui Xing、Yuan-Xi Liao、Jaclynn Ng、Qiao-Sheng Hu

  DOI：10.1021/jo200302x

  日期：2011.5.20

  of optically active 1,1′-spirobiindane-7,7′-diol (SPINOL)-based phosphoric acids are described. These SPINOL-based phosphoric acids were prepared from (R)-SPINOL in three steps and exhibited excellent enantioselectivities for the reactions of indoles with aldimines and β,γ-unsaturated-α-ketoesters. Our study provides a family of promising chiral phosphoric acids to the asymmetric organocatalysis toolbox

  描述了一系列光学活性的1,1'-螺双茚满-7,7'-二醇（SPINOL）基磷酸的合成和应用。由（R）-SPINOL分三步制备这些基于SPINOL的磷酸，它们对于吲哚与醛亚胺和β，γ-不饱和α-酮酸酯的反应显示出极好的对映选择性。我们的研究为不对称有机催化工具箱提供了一系列有前途的手性磷酸。
• Py-2NO ligand enabled Ni(<scp>ii</scp>)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters
  作者：Zi-Yue Chen、Xi-Rui Wang、Ke-Lan Xu、Pan Hu、You-Ping Tian、Hui-Juan Wang、Ying Zhou、Xiong-Li Liu

  DOI：10.1039/d3nj05076a

  日期：——

  development of chiral ligands to fine-tune stereocontrol in asymmetric catalysis is of great demand. To diversify the Py-2NO ligand library recently developed by our group, herein, we synthesized six new Py-2NO ligands, determined the absolute configuration via X-ray crystallographic study of ligand L1g, and applied these ligands in the Ni(II)-catalyzed asymmetric Michael addition reaction of indoles and

  开发用于微调不对称催化立体控制的手性配体的需求很大。为了丰富我们课题组最近开发的Py-2NO配体库，我们合成了6种新的Py-2NO配体，通过配体L1g的X射线晶体学研究确定了其绝对构型，并将这些配体应用于Ni( II )-催化吲哚和β,γ-不饱和α-酮酯的不对称迈克尔加成反应。在温和条件下，多种底物均获得了优异的产率（高达 93%）和高对映选择性（高达 99% ee）。此外，我们通过X射线晶体学研究发现叔胺衍生的N-氧化物产物中的C（芳基）-N（酰胺）键存在轴向手性。由于阻转异构现象的有趣特征，我们相信该反应将为轴向手性家族添加一个重要成员。
• Phen-2NO, a new <i>C</i>₂-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles
  作者：Zi-Yue Chen、Ke-Lan Xu、Xi-Rui Wang、Pan Hu、Wei-Yan Jiang、Yi-Feng Dai、Li-Jun Peng、Xiong-Li Liu

  DOI：10.1039/d4nj00088a

  日期：2024.4.15

  great coordination ability with various ions, the development of new chiral phen ligands is in great demand in asymmetric catalysis. Herein, we rationally designed and developed an entirely new class of C2-symmetric rigid-featured chiral phen ligands that provide the N,N,O,O-tetradentate coordination of the phen moiety and two additional N,N-dioxides. The chiral ligands, termed Phen-2NO ligands, incorporate

  由于菲咯啉（phen）与各种离子具有很强的配位能力，因此不对称催化中迫切需要开发新型手性phen配体。在此，我们合理地设计和开发了一类全新的C 2 -对称刚性特征手性phen配体，其提供了phen部分的N , N , O , O -四齿配位和两个额外的N , N -二氧化物。手性配体，称为 Phen-2NO 配体，结合了 phen 骨架和基于吡咯并咪唑啉酮的N-氧化物部分的优点，并且可以通过在酰胺芳环中引入取代基来轻松调整其电子和空间性质。团体。这些配体在 Ni( II ) 催化的吲哚与 β,γ-不饱和 α-酮酯的不对称 Michael 型 Friedel-Crafts 烷基化反应中表现出优异的性能。在温和条件下，多种底物均获得优异的产率（高达 93%）和高对映选择性（高达 99% ee）。这些结果证明了 Phen-2NO 配体作为有效的手性 phen 配体的巨大潜力。
• Phosphonium ion tagged chiral phosphoric acids and their application in Friedel–Crafts reactions of indoles
  作者：Julia Hermeke、Patrick H. Toy

  DOI：10.1016/j.tet.2011.03.105

  日期：2011.6

  The attachment of phosphonium ion phase tags to chiral binapthyl-based phosphoric acid catalysts, and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles has been studied. Placement of the tags at the 3 and 3' positions of the phosphoric acid, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6' positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily removed at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• AgAsF₆/Sm(OTf)₃ Promoted Reversal of Enantioselectivity for the Asymmetric Friedel−Crafts Alkylations of Indoles with β,γ-Unsaturated α-Ketoesters
  作者：Yanling Liu、Deju Shang、Xin Zhou、Yin Zhu、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/ol902587t

  日期：2010.1.1

  The first example of central metal controlled reversal of enantioselectivity in asymmetric Friedel-Crafts alkylation of Indoles and beta,gamma-unsaturated alpha-ketoesters has been developed. Using the same chiral starting material derived N,N'-dioxides 1 a and 1 b as ligands, various indole esters 4 were obtained In good to excellent yields and enantioselectivities. The reaction also featured mild reaction conditions and remarkably low catalyst loading (down to 0.01 mol %).