1-(4-bromophenyl)pent-4-en-1-one-3,3-d2 | 1201909-78-5

• 英文名称: 1-(4-bromophenyl)pent-4-en-1-one-3,3-d2
• CAS: 1201909-78-5
• 化学式: C₁₁H₁₁BrO
• 分子量: 241.096
• InChiKey: ZRCKLFJMCKAXJX-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)pent-4-en-1-one-3,3-d2 、 甲基三苯基碘化膦 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到1-bromo-4-(hexa-1,5-dien-2-yl-4,4-d2)benzene
  参考文献：
  名称：

  Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes

  摘要：

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

  DOI：

  10.1021/ol902505p
• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.5 g的产率得到1-(4-bromophenyl)pent-4-en-1-one-3,3-d2
  参考文献：
  名称：

  Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes

  摘要：

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

  DOI：

  10.1021/ol902505p