(3'S)-(E)-2-acetyl-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole | 170882-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3'S)-(E)-2-acetyl-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole
• 英文别名: 1-[4-[(E)-2-[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]ethenyl]-1-(ethoxymethyl)imidazol-2-yl]ethanone
• CAS: 170882-83-4
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: SIVAOWZWZCNHHX-HVHJFMEUSA-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：

  (3'S)-(E)-2-acetyl-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole 在 盐酸 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 121.5h， 生成 1-[4-(1,2,3,4-四羟基丁基)-1H-咪唑-2-基]乙酮
  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：

  (4S)-2,2-diethyl-4-(2',2'-dibromoethenyl)-1,3-dioxolane 在 Lindlar's catalyst 喹啉 、 四(三苯基膦)钯 、 正丁基锂 、 三甲基氯化锡 、 氢气 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.58h， 生成 (3'S)-(E)-2-acetyl-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole
  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 (1R, 2S, 3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole
  作者：Matthew D Cliff、Stephen G Pyne

  DOI：10.1016/0040-4039(95)01155-b

  日期：1995.8

  A method for preparing the biologically active compound (1R, 2S, 3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole1 using a palladium (0) catalysed coupling of 1-ethoxymethyl-4-iodoimidazole 2 to the functionalised vinylstannane 3 and the Sharpless catalytic asymmetric dihydroxylation is reported.

  一种使用钯（0）催化偶合制备生物活性化合物（1 R，2 S，3 R）-2-乙酰基-4（5）-（1,2,3,4-四羟基丁基）咪唑1的方法报道了将1-乙氧基甲基-4-碘咪唑2官能化成乙烯基锡烷3和Sharpless催化不对称二羟基化反应。
• 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.