（3R）-（-）-3-（1-甲基吲哚-3-基）丁酸甲酯 | 460050-72-0

• 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
• 中文名称: （3R）-（-）-3-（1-甲基吲哚-3-基）丁酸甲酯
• 英文名称: (R)-methyl-3-(1-methyl-1H-indol-3-yl)butanoate
• 英文别名: methyl (R)-3-(1-methyl-1H-indol-3-yl)butanoate；Methyl (3R)-(-)-3-(1-methylindol-3-yl)butanoate；methyl (3R)-3-(1-methylindol-3-yl)butanoate
• CAS: 460050-72-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: QIOUBQLAFUPETC-SNVBAGLBSA-N

物化性质

• 沸点：
  350.4±17.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-1-(1-甲基-1H-咪唑-2-基)-3-(1-甲基-1H-吲哚-3-基)丁烷-1-酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 （3R）-（-）-3-（1-甲基吲哚-3-基）丁酸甲酯
  参考文献：
  名称：

  双(恶唑啉基)吡啶-钪(III)三氟甲磺酸盐配合物催化α,β-不饱和2-酰基咪唑的对映选择性Friedel-Crafts烷基化

  摘要：

  已经完成了由双（恶唑啉基）吡啶-钪（III）三氟甲磺酸盐配合物催化的α，β-不饱和2-酰基咪唑和富电子芳香亲核试剂的对映选择性Friedel-Crafts烷基化反应。这些 α,β-不饱和 2-酰基咪唑是 Friedel-Crafts 反应的有效亲电试剂。通过甲基化和随后的咪唑残基置换，所得加合物 2-酰基咪唑很容易转化为酰胺、酯、羧酸、酮和醛。

  DOI：

  10.1021/ja052433d

文献信息

• Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-quinolinolato) Aluminum Complexes
  作者：Norito Takenaka、Joshua P. Abell、Hisashi Yamamoto

  DOI：10.1021/ja0668320

  日期：2007.1.1

  aluminum(III) complexes effectively catalyze the highly enantioselective Mukaiyama−Michael reaction of silyl enol ethers, including tetrasubstituted enolates that give rise to enantioenriched α-carbonyl all-carbon-substituted quaternary stereocenters. The present catalyst also promotes the conjugate addition of N-benzylindole to α,β-unsaturated acylphosphonates with high enantioselectivity (indole Friedel−Crafts

  新的手性系链双（8-羟基喹啉）（TBOx）铝（III）配合物有效催化甲硅烷基烯醇醚的高度对映选择性 Mukaiyama-Michael 反应，包括产生对映体富集的 α-羰基全碳取代四元立体中心的四取代烯醇化物。本催化剂还促进了 N-苄基吲哚与具有高对映选择性的 α,β-不饱和酰基膦酸酯的共轭加成（吲哚 Friedel-Crafts 烷基化反应）。
• Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with β,γ-Unsaturated α-Keto Phosphonates in the Presence of Chiral Palladium Complexes
  作者：Dae Kim、Young Kang、Ki Suh

  DOI：10.1055/s-0030-1259932

  日期：2011.5

  The catalytic enantioselective Friedel―Crafts alkylation reaction promoted by chiral palladium complexes is described. The treatment of indoles with β,γ-unsaturated α-keto phosphonates under the mild reaction conditions afforded the corresponding Friedel―Crafts alkylation adducts with excellent enantioselectivities (up to 99% ee).

  描述了手性钯配合物促进的催化对映选择性Friedel-Crafts烷基化反应。在温和的反应条件下用 β,γ-不饱和 α-酮膦酸酯处理吲哚，得到相应的 Friedel-Crafts 烷基化加合物，具有优异的对映选择性（高达 99% ee）。
• Enantioselective Friedel−Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes
  作者：David A. Evans、Keith R. Fandrick、Hyun-Ji Song、Karl A. Scheidt、Risheng Xu

  DOI：10.1021/ja072976i

  日期：2007.8.1

  The enantioselective Friedel-Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes (Sc(III)-pybox) was accomplished utilizing a series of beta-substituted alpha,beta-unsaturated phosphonates and alpha,beta-unsaturated 2-acyl imidazoles. The acyl phosphonate products were efficiently transformed into esters and amides, whereas the acyl imidazole adducts were converted to a broader spectrum of functionalities such as esters, amides, carboxylic acids, ketones, and aldehydes. The sense of stereoinduction and level of enantioselectivity were found to be functions of the size of the substrate employed, the substitution on the ligand, and the catalyst loading. Molecular modeling of the catalyst with the bound substrates was performed based on the crystal structures of the catalyst complexes and the sense of stereoinduction observed in the addition reaction. Nonlinear effects over a range of catalyst concentrations implicate a mononuclear complex as the active catalyst.