(2E)-6-bromohex-2-enoic chloride | 1026844-29-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (2E)-6-bromohex-2-enoic chloride
• 英文别名: (E)-6-bromohex-2-enoyl chloride
• CAS: 1026844-29-0
• 化学式: C₆H₈BrClO
• 分子量: 211.486
• InChiKey: DDHPTFGTWCWNIM-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-6-bromohex-2-enoic chloride 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以40%的产率得到(4S)-3-[(E)-6-bromohex-2-enoyl]-4-isopropyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

  摘要：

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.

  DOI：

  10.1021/jo0107296
• 作为产物：
  描述：

  (E)-ethyl 6-bromohex-2-enoate 在 氯化亚砜 作用下， 反应 4.0h， 生成 (2E)-6-bromohex-2-enoic chloride
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

  摘要：

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.

  DOI：

  10.1021/jo0107296

文献信息

• Palladium-Catalyzed Sequential Alkylation−Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings
  作者：Mark Lautens、Jean-François Paquin、Sandrine Piguel、Marc Dahlmann

  DOI：10.1021/jo0107296

  日期：2001.11.1

  The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromo-enoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.