2-bromo-5-hydroxy-3-methyl-nona-2c,4t-dienoic acid-lactone | 99187-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-bromo-5-hydroxy-3-methyl-nona-2c,4t-dienoic acid-lactone
• 英文别名: 2-Brom-5-hydroxy-3-methyl-nona-2c,4t-diensaeure-lacton；3-Bromo-6-butyl-4-methylpyran-2-one
• CAS: 99187-46-9
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: NJHOPHFPFYISMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  chlorozinc(1+),hex-1-yne 在 四(三苯基膦)钯 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2-bromo-5-hydroxy-3-methyl-nona-2c,4t-dienoic acid-lactone
  参考文献：
  名称：

  A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

  摘要：

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00322-0

文献信息

• Notes - 2-Pyrones. XXVII. 4-Methyl-6-alkyl-2-pyrones
  作者：Richard Wiley、J. Esterle

  DOI：10.1021/jo01361a605

  日期：1957.10
• A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones
  作者：Renzo Rossi、Fabio Bellina、Luisa Mannina

  DOI：10.1016/s0040-4039(98)00322-0

  日期：1998.5

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.