(S)-ethyl 2-ethoxycarbonyl-3-(3-indolyl)-3-(m-bromophenyl)Propanoate | 1220654-52-3

• 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: (S)-ethyl 2-ethoxycarbonyl-3-(3-indolyl)-3-(m-bromophenyl)Propanoate
• 英文别名: diethyl (S)-2-[(3-bromophenyl)(1H-indol-3-yl)methyl]malonate；diethyl 2-[(S)-(3-bromophenyl)-(1H-indol-3-yl)methyl]propanedioate
• CAS: 1220654-52-3
• 化学式: C₂₂H₂₂BrNO₄
• 分子量: 444.325
• InChiKey: PFNROFWPCZRRBG-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲哚 、 diethyl 2-(3-bromobenzylidene)malonate 在 bis[(S)-4-(isopropyl)oxazoline-2-yl]-2-(thienyl)-ethene 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 异丁醇 为溶剂， 反应 12.0h， 以96%的产率得到(S)-ethyl 2-ethoxycarbonyl-3-(3-indolyl)-3-(m-bromophenyl)Propanoate
  参考文献：
  名称：

  杂亚芳基丙二酸酯衍生的双（恶唑啉）铜（II）配合物催化吲哚与亚炔基丙二酸酯的高对映选择性弗里德-克拉夫特反应

  摘要：

  合成了一系列廉价且易于获得的杂芳基丙二酸酯衍生的双（恶唑啉）配体1和2，并将它们的铜（II）配合物用于吲哚和烷基亚乙基丙二酸酯之间的Friedel-Crafts催化反应，S具有出色的不对称对映选择性-对映异构体（最高> 99％ee）在异丁醇中，R-对映异构体（最高96.5％ee）在二氯甲烷中。

  DOI：

  10.1002/adsc.200900669

文献信息

• Synthesis of New C2- Symmetric Fluoren-9-ylidene Malonate Derived Bis(oxazoline) Ligands and Their Application in Friedel-Crafts Reactions
  作者：Jing Li、Hong-Liang Chen、Lei Liu、Bin Fu

  DOI：10.3390/molecules15128582

  日期：——

  series of new C(2)-symmetric fluoren-9-ylidene malonate-derived bis(oxazoline) ligands were synthesized from fluoren-9-ylidene malonate and enantiomerically pure amino alcohols via a convenient route. Their asymmetric catalytic properties in the Friedel-Crafts reactions of indoles with arylidene malonates were evaluated, and the Cu(OTf)2 complex of a fluoren-9-ylidene malonate-derived bis(oxazoline) bearing

  一系列新的 C(2)-对称芴 9-ylidene 丙二酸酯派生的 bis(oxazoline) 配体是通过方便的路线从芴 9-ylidene 丙二酸酯和对映体纯氨基醇合成的。评估了它们在吲哚与亚芳基丙二酸酯的 Friedel-Crafts 反应中的不对称催化性能，并且带有苯基的芴-9-亚基丙二酸酯衍生的双（恶唑啉）的 Cu(OTf)2 络合物显示出中等至良好的对映选择性。高达 88% ee）。
• Mechanochemical Copper‐Catalyzed Asymmetric Michael‐Type Friedel–Crafts Alkylation of Indoles with Arylidene Malonates
  作者：Plamena Staleva、José G. Hernández、Carsten Bolm

  DOI：10.1002/chem.201901826

  日期：2019.7.11

  asymmetric Michael‐type Friedel–Crafts alkylation of indoles with arylidene malonates was developed. The reaction proceeds under ambient atmosphere using a chiral bis(oxazoline)copper catalyst in a mixer mill. Under these reaction conditions nineteen 3‐substituted indole derivatives were synthesized in good to excellent yields (up to 98 %), and with good enantioselectivities (up to 91:9 e.r.) after short milling

  开发了机械化学形式的吲哚与丙二烯基丙二酸酯的不对称Michael型Friedel-Crafts烷基化反应。反应在环境气氛下使用手性双（恶唑啉）铜催化剂在混合机中进行。在这些反应条件下，经过短时间的研磨，合成了19种3取代的吲哚衍生物，收率好至极好（高达98％），对映选择性（高达91：9 er）。
• Highly Enantioselective Friedel–Crafts Reaction of Indole with Alkylidenemalonates Catalyzed by Heteroarylidene Malonate-Derived Bis(oxazoline) Copper(II) Complexes
  作者：Yan-Jin Sun、Nan Li、Zhong-Bo Zheng、Lei Liu、Yan-Bo Yu、Zhao-Hai Qin、Bin Fu

  DOI：10.1002/adsc.200900669

  日期：2009.12

  A series of cheap and easily accessible heteroarylidenemalonate-derived bis(oxazoline) ligands 1 and 2 were synthesized and their copper(II) complexes were applied to the catalytic Friedel–Crafts reaction between indoles and diethyl alkylidenemalonates, Excellent asymmetric enantioselectivities were afforded for the S-enantiomer (up to >99% ee) in isobutyl alcohol, and the R-enantiomer (up to 96.5%

  合成了一系列廉价且易于获得的杂芳基丙二酸酯衍生的双（恶唑啉）配体1和2，并将它们的铜（II）配合物用于吲哚和烷基亚乙基丙二酸酯之间的Friedel-Crafts催化反应，S具有出色的不对称对映选择性-对映异构体（最高> 99％ee）在异丁醇中，R-对映异构体（最高96.5％ee）在二氯甲烷中。
• N,N′-Dioxide–scandium(III) complex catalyzed highly enantioselective Friedel–Crafts alkylation of indole to alkylidene malonates
  作者：Yanling Liu、Xin Zhou、Deju Shang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2009.12.032

  日期：2010.2

  A highly efficient enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates has been developed using chiral N,N'-dioxide LA-scandium(III) complex as the catalyst, giving the corresponding products in high yields with excellent enantioselectivities (up to 99% yield and 95% ee). The product 3a was facilely converted into several interesting compounds, such as tryptamines, indolepropionic acids and beta-carbolines. It is noteworthy that the seven-membered beta-carboline-like compound has been synthesized for the first time. Based on the crystal structure of the chiral N,N'-dioxide L10-scandium(III) complex, the proposed transition state and possible catalytic cycle were presented to elucidate the reaction mechanism. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of heteroarylidene malonate derived bis(thiazolines) and their application in the catalyzed Friedel–Crafts reaction
  作者：Lei Liu、Jing Li、Mingan Wang、Fengpei Du、Zhaohai Qin、Bin Fu

  DOI：10.1016/j.tetasy.2011.03.003

  日期：2011.3

  A series of novel heteroarylidene malonate derived bis(thiazoline) ligands 1 and 2 were synthesized and applied to a Friedel-Crafts reaction between indole and alkylidene malonate. The Cu(OTf)(2) complex of ligand 2b bearing a benzyl group afforded moderate to excellent enantioselectivity for the adducts (up to >99% ee). (C) 2011 Elsevier Ltd. All rights reserved.