(S)-4-methyl-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-1H-indol-3-yl)pentan-1-one

• 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)-4-methyl-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-1H-indol-3-yl)pentan-1-one
• 英文别名: (3S)-4-methyl-1-(1-methylimidazol-2-yl)-3-(1-methylindol-3-yl)pentan-1-one
• 化学式: C₁₉H₂₃N₃O
• 分子量: 309.411
• InChiKey: ZKSQMSOHGIUDGZ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  39.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2E)-4-methylpent-2-enoic acid 在 正丁基锂 、 4 A molecular sieve 、 Sc(III)-(S,S)-inda-pybox)(OTf)3 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 8.0h， 生成 (S)-4-methyl-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-1H-indol-3-yl)pentan-1-one
  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

• 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.
• Enantioselective Friedel−Crafts Alkylations of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes
  作者：David A. Evans、Keith R. Fandrick、Hyun-Ji Song

  DOI：10.1021/ja052433d

  日期：2005.6.1

  An enantioselective Friedel−Crafts alkylation with α,β-unsaturated 2-acyl imidazoles and electron-rich aromatic nucleophiles catalyzed by bis(oxazolinyl)pyridine−scandium(III) triflate complexes has been accomplished. These α,β-unsaturated 2-acyl imidazoles are effective electrophiles for the Friedel−Crafts reaction. The resulting adduct 2-acyl imidazole is easily converted to amides, esters, carboxylic

  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。