(S)-ethyl 2-ethoxycarbonyl-3-[3-(7-chloroindolyl)]-3-phenylpropanoate | 1220654-58-9

• 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-(7-chloroindolyl)]-3-phenylpropanoate
• 英文别名: (S)-ethyl 2-ethoxycarbonyl-3-[3-(5-chloroindolyl)]-3-phenylpropanoate；(S)-ethyl 2-ethoxycarbonyl-3-[5-chloroindol-3-yl]-3-phenylpropanoate；diethyl 2-[(S)-(5-chloro-1H-indol-3-yl)-phenylmethyl]propanedioate
• CAS: 1220654-58-9
• 化学式: C₂₂H₂₂ClNO₄
• 分子量: 399.874
• InChiKey: DGJDHOCLTIMEOA-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：

  5-氯吲哚 、 亚苯甲基丙二酸二乙酯 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99%的产率得到(S)-ethyl 2-ethoxycarbonyl-3-[3-(7-chloroindolyl)]-3-phenylpropanoate
  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

• Malonate-type bis(oxazoline) ligands with sp2 hybridized bridge carbon: synthesis and application in Friedel–Crafts alkylation and allylic alkylation
  作者：Hongliang Chen、Fengpei Du、Lei Liu、Jing Li、Qiuying Zhao、Bin Fu

  DOI：10.1016/j.tet.2011.09.106

  日期：2011.12

  the Friedel–Crafts reaction and allylic alkylation. The Cu(II) complex of ligand 4b bearing the benzyl group afforded good to excellent enantioselectivity for the F–C adducts (up to >99% ee) between indole and alkylidene malonate, and the palladium complex of ligand 4c bearing the phenyl group afforded excellent enantioselectivity (up to 94% ee) for the allylic alkylation product.

  合成了一系列简单且新颖的C 2对称的二苯基亚甲基丙二酸酯型双（恶唑啉）配体，并将其应用于Friedel-Crafts反应和烯丙基烷基化反应。铜（II）配合物的配体的图4b带有苄基，得到良好至优异的对映选择性为˚F - Ç吲哚和亚丙二之间加合物（高达> 99％ee）的，和钯配合物的配体的4C带有苯基，得到对烯丙基烷基化产物具有优异的对映选择性（高达94％ee）。
• 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）。
• 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。
• 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.
• Cu(OTf)₂-Catalyzed Asymmetric Friedel–Crafts Alkylation Reaction of Indoles with Arylidene Malonates Using Bis(sulfonamide)-Diamine Ligands
  作者：Jing Wu、Dongping Wang、Fan Wu、Boshun Wan

  DOI：10.1021/jo400747d

  日期：2013.6.7

  highly efficient Cu-catalyzed asymmetric Friedel Crafts alkylation reaction of indoles with arylidene malonates using simple, stable, and easily prepared bis-sulfonamide diamine ligands was developed. The desired products were obtained in up to 99% yield with 96% ee.