(3'S)-(E)-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole | 170882-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'S)-(E)-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole
• 英文别名: (3'S)-(E)-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-ethoxymethylimidazole；4-[(E)-2-[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]ethenyl]-1-(ethoxymethyl)imidazole
• CAS: 170882-82-3
• 化学式: C₁₅H₂₄N₂O₃
• 分子量: 280.367
• InChiKey: OFOQIESICQCXIO-NPQIQWPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'S)-(E)-4-<3',4'-O-(3'-pentylidene)-3',4'-dihydroxybut-1'-enyl>-1-(ethoxymethyl)imidazole 在 盐酸 、 正丁基锂 、 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 125.0h， 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：

  2,3-O-(3-亚戊基)-d-甘油醛 在 四(三苯基膦)钯 、 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 76.5h， 生成 (3'S)-(E)-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

• Palladium catalysed coupling of imidazoles to alkynyl and vinyl substrates
  作者：Matthew D Cliff、Stephen G Pyne

  DOI：10.1016/0040-4020(96)00823-x

  日期：1996.10

  Methods for preparing 4-substituted imidazoles from the palladium(0) catalysed couplings of N-protected 4-haloimidazoles with alkynes or alkynyl- and vinyltrialkyltin derivatives or from the coupling reactions of 4-trimethylstannylimidazole 9 with aryl and vinyliodides and bromides under Stille conditions is reported.

  由N-保护的4-卤代咪唑与炔烃或炔基和乙烯基三烷基锡衍生物的钯（0）催化偶合或在Stille条件下由4-三甲基苯乙烯基咪唑9与芳基和乙烯基碘化物及溴化物的偶合反应制备4-取代的咪唑的方法是报告。
• 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.