1-{4-[(Z)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-vinyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone | 185798-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{4-[(Z)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-vinyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone
• 英文别名: 1-[4-[(Z)-2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]ethenyl]-1-(ethoxymethyl)imidazol-2-yl]ethanone
• CAS: 185798-11-2
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: SIVAOWZWZCNHHX-WHLNPGIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-{4-[(Z)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-vinyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone 在 potassium osmate(VI) 、 AD-mix-α 、 甲基磺酰胺 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 1-{4-[(1R,2R)-2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-1,2-dihydroxy-ethyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone 、 1-{4-[(1S,2S)-2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-1,2-dihydroxy-ethyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles

  摘要：

  A method for preparing the eight stereoisomers of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI, 1) is reported. This method employs a palladium(0)-catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (7) to functionalized vinylstannanes (R)- or (S)-12a,b or 13a,b or 1-alkynylstannanes (R)- or (S)-6a,b to introduce the C-4 imidazole four-carbon side chain. The 1,2-dihydroxy functionality of the butyl side chain was introduced by Sharpless catalytic asymmetric dihydroxylation reactions.

  DOI：

  10.1021/jo961630f
• 作为产物：
  描述：

  4-[2-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]ethynyl]-1-(ethoxymethyl)imidazole 在 Lindlar's catalyst 喹啉 、 正丁基锂 、 氢气 作用下， 以 正己烷 为溶剂， 反应 5.5h， 生成 1-{4-[(Z)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-vinyl]-1-ethoxymethyl-1H-imidazol-2-yl}-ethanone
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles

  摘要：

  A method for preparing the eight stereoisomers of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI, 1) is reported. This method employs a palladium(0)-catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (7) to functionalized vinylstannanes (R)- or (S)-12a,b or 13a,b or 1-alkynylstannanes (R)- or (S)-6a,b to introduce the C-4 imidazole four-carbon side chain. The 1,2-dihydroxy functionality of the butyl side chain was introduced by Sharpless catalytic asymmetric dihydroxylation reactions.

  DOI：

  10.1021/jo961630f

文献信息

• Asymmetric Synthesis of 2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles
  作者：Matthew D. Cliff、Stephen G. Pyne

  DOI：10.1021/jo961630f

  日期：1997.2.1

  A method for preparing the eight stereoisomers of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI, 1) is reported. This method employs a palladium(0)-catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (7) to functionalized vinylstannanes (R)- or (S)-12a,b or 13a,b or 1-alkynylstannanes (R)- or (S)-6a,b to introduce the C-4 imidazole four-carbon side chain. The 1,2-dihydroxy functionality of the butyl side chain was introduced by Sharpless catalytic asymmetric dihydroxylation reactions.