2-methyl-4-(benzoyloxy)-pent-2-enoic acid methyl ester | 887130-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-4-(benzoyloxy)-pent-2-enoic acid methyl ester
• 英文别名: [(E)-5-methoxy-4-methyl-5-oxopent-3-en-2-yl] benzoate
• CAS: 887130-03-2
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: QHKZTCNLHXNLHM-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(benzoyloxy)-pent-2-enoic acid methyl ester 、 2-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde 在 palladium diacetate 、 diethylzinc 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以984 mg的产率得到(S,S)-2-{[2-(tert-butyldimethylsilanyloxymethyl)-phenyl]-hydroxymethyl}-2-methylpent-3-enoic acid methyl ester
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f
• 作为产物：
  描述：

  反-2-甲基-2-戊烯酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-methyl-4-(benzoyloxy)-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f

文献信息

• New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements
  作者：Yi-Hung Chen、Frank E. McDonald

  DOI：10.1021/ja061082f

  日期：2006.4.1

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.