(E)-2,3-dibromo-4-methylpent-2-enoic acid | 1360895-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2,3-dibromo-4-methylpent-2-enoic acid
• CAS: 1360895-23-3
• 化学式: C₆H₈Br₂O₂
• 分子量: 271.936
• InChiKey: MVQOYNOGGBNJPO-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,3-dibromo-4-methylpent-2-enoic acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.25h， 生成 (Z)-3-benzyl-5-(3-chloro-4-methoxybenzylidene)-4-isopropylfuran-2(5H)-one
  参考文献：
  名称：

  铜催化的多米诺骨牌路线向天然的Nosoclides及其类似物：Nostoclides I和II的全合成。

  摘要：

  AbstractAn original and convenient domino route to natural nostoclides I and II has been developed using a two‐step sequence consisting of a copper‐catalyzed tandem reaction associated with Suzuki cross‐coupling. The methodology employed for this total synthesis appeared to be an interesting and sufficiently flexible tool to allow the synthesis of numerous analogues of these nostoclides.magnified image

  DOI：

  10.1002/adsc.201300459
• 作为产物：
  描述：

  ethyl 4-methylpent-2-ynoate 在 溴 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (E)-2,3-dibromo-4-methylpent-2-enoic acid
  参考文献：
  名称：

  铜催化的多米诺骨牌路线向天然的Nosoclides及其类似物：Nostoclides I和II的全合成。

  摘要：

  AbstractAn original and convenient domino route to natural nostoclides I and II has been developed using a two‐step sequence consisting of a copper‐catalyzed tandem reaction associated with Suzuki cross‐coupling. The methodology employed for this total synthesis appeared to be an interesting and sufficiently flexible tool to allow the synthesis of numerous analogues of these nostoclides.magnified image

  DOI：

  10.1002/adsc.201300459

文献信息

• Carboxylate-Directed Tandem Functionalisations of α,β-Dihaloalkenoic Acids with 1-Alkynes: A Straightforward Access to (Z)-Configured, α,β-Substituted γ-Alkylidenebutenolides
  作者：Samuel Inack Ngi、Khalil Cherry、Virginie Héran、Laurent Commeiras、Jean-Luc Parrain、Alain Duchêne、Mohamed Abarbri、Jérôme Thibonnet

  DOI：10.1002/chem.201102570

  日期：2011.12.2

  and stereoselectively leads to rarely described (Z)‐3‐halo‐5‐ylidene‐5H‐furan‐2‐ones. These compounds are subsequently able to undergo classical Pd‐catalysed cross‐coupling reactions, providing 3‐substituted and 3,4‐disubstituted 5‐ylidene‐5H‐furan‐2‐ones (see scheme).

  容易和温和的铜（I）催化的易获得的（E）-2,3-二卤代丙酸衍生物的区域选择性和立体选择性内酯化导致很少描述的（Z）-3-卤代-5-亚烷基-5 H-呋喃- 2个 这些化合物随后能够进行经典的Pd催化的交叉偶联反应，提供3-取代的和3,4-二取代的5-亚烷基-5 H-呋喃-2-（参见方案）。
• Copper-Catalyzed Domino Route to Natural Nostoclides and Analogues: A Total Synthesis of Nostoclides I and II
  作者：Samuel Inack Ngi、Julien Petrignet、Romain Duwald、El Mostafa El Hilali、Mohamed Abarbri、Alain Duchêne、Jérôme Thibonnet

  DOI：10.1002/adsc.201300459

  日期：2013.10.11

  AbstractAn original and convenient domino route to natural nostoclides I and II has been developed using a two‐step sequence consisting of a copper‐catalyzed tandem reaction associated with Suzuki cross‐coupling. The methodology employed for this total synthesis appeared to be an interesting and sufficiently flexible tool to allow the synthesis of numerous analogues of these nostoclides.magnified image