(+)-ethyl 2-ethoxycarbonyl-3-[3-(4-methoxyindolyl)]-3-phenylpropanoate

• 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 2-ethoxycarbonyl-3-[3-(4-methoxyindolyl)]-3-phenylpropanoate
• 英文别名: diethyl 2-[(4-methoxy-1H-indol-3-yl)-phenylmethyl]propanedioate
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: DVFPQMIAKYSRSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基吲哚 、 亚苯甲基丙二酸二乙酯 在 1,2,2-tris[(4S)-4-iPr-4,5-dihydro-1,3-oxazol-2-yl]propane 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 异丁醇 为溶剂， 反应 50.0h， 以98%的产率得到(+)-ethyl 2-ethoxycarbonyl-3-[3-(4-methoxyindolyl)]-3-phenylpropanoate
  参考文献：
  名称：

  Controllable Enantioselective Friedel−Crafts Reaction¹ between Indoles and Alkylidene Malonates Catalyzed by Pseudo-C₃-Symmetric Trisoxazoline Copper(II) Complexes

  摘要：

  Pseudo-C-3-symmetric trisoxazoline copper(II) complexes prove to be excellent catalysts in the Friedel-Crafts alkylation of indoles with alkylidene malonates. The absolute stereochemistry of this reaction is shown to be dependent on the solvent. Reactions in isobutyl alcohol afford the Friedel-Crafts alkylation adducts in excellent yields and with up to +98% ee. In 1,1,2,2-tetrachloroethane (TTCE), however, the opposite enantiomers of the products are obtained in good yields with up to -89% ee. Water tolerance of chiral catalyst trisoxazoline 2a/Cu(OTf)(2) is examined, and it is found that the addition of up to 200 equiv of water relative to catalyst in isobutyl alcohol has almost no effect on enantioselectivity but slows down the reaction. The reaction scope is studied as well. The roles of alcohol as the solvent to accelerate the reaction are discussed. The stereochemical models of asymmetric induction for reactions both in isobutyl alcohol and in TTCE are also developed.

  DOI：

  10.1021/jo035552p

文献信息

• Methods for synthesis of 3-amino-1-arylpropyl indoles
  申请人：Connolly Joseph Terrence

  公开号：US20070135647A1

  公开（公告）日：2007-06-14

  A method comprising: hydrogenating an indole propionamide compound of formula h with vitride, to form an aminopropyl indole compound of formula i wherein m, Ar, R 1 and R 2 are as defined herein. The compounds prepared by the method of the invention are useful as monoamine reuptake inhibitors useful for treatment of CNS indications.

  一种方法包括：使用氢化剂对化学式为h的吲哚丙酰胺化合物进行氢化，以形成化学式为i的氨基丙基吲哚化合物，其中m、Ar、R1和R2如本文所定义。本发明的方法制备的化合物可用作单胺再摄取抑制剂，适用于中枢神经系统适应症的治疗。
• METHODS FOR SYNTHESIS OF 3-AMINO-1-ARYLPROPYL INDOLES
  申请人：F.Hoffmann-La Roche AG

  公开号：EP1957454B1

  公开（公告）日：2011-07-20
• US7598399B2
  申请人：——

  公开号：US7598399B2

  公开（公告）日：2009-10-06
• [EN] METHODS FOR SYNTHESIS OF 3-AMINO-1-ARYLPROPYL INDOLES<br/>[FR] PROCEDE DE SYNTHESE DE 3-AMINO-1-ARYLPROPYLE INDOLES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2007062994A1

  公开（公告）日：2007-06-07

  [EN] A method comprising: hydrogenating an indole propionamide compound of formula h with vitride, to form an aminopropyl indole compound of formula I wherein m, Ar, R¹ and R² are as defined herein. The compounds prepared by the method of the invention are useful as monoamine reuptake inhibitors useful for treatment of CNS indications.
  [FR] La présente invention se rapporte à un procédé qui consiste : à hydrogéner un composé propionamide indole représenté par la formule h avec du vitride, afin de former un composé aminopropyle indole représenté par la formule i, dans laquelle m, Ar, R¹ et R² sont tels que définis dans le descriptif de l'invention. Les composés préparés par le procédé selon l'invention sont utiles en tant qu'inhibiteurs du recaptage des monoamines pour le traitement de troubles du SNC.
• Controllable Enantioselective Friedel−Crafts Reaction¹ between Indoles and Alkylidene Malonates Catalyzed by Pseudo-<i>C</i>₃-Symmetric Trisoxazoline Copper(II) Complexes
  作者：Jian Zhou、Meng-Chun Ye、Zheng-Zheng Huang、Yong Tang

  DOI：10.1021/jo035552p

  日期：2004.2.1

  Pseudo-C-3-symmetric trisoxazoline copper(II) complexes prove to be excellent catalysts in the Friedel-Crafts alkylation of indoles with alkylidene malonates. The absolute stereochemistry of this reaction is shown to be dependent on the solvent. Reactions in isobutyl alcohol afford the Friedel-Crafts alkylation adducts in excellent yields and with up to +98% ee. In 1,1,2,2-tetrachloroethane (TTCE), however, the opposite enantiomers of the products are obtained in good yields with up to -89% ee. Water tolerance of chiral catalyst trisoxazoline 2a/Cu(OTf)(2) is examined, and it is found that the addition of up to 200 equiv of water relative to catalyst in isobutyl alcohol has almost no effect on enantioselectivity but slows down the reaction. The reaction scope is studied as well. The roles of alcohol as the solvent to accelerate the reaction are discussed. The stereochemical models of asymmetric induction for reactions both in isobutyl alcohol and in TTCE are also developed.