3-溴-3-苯基丁烷-2-酮 | 35307-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-3-苯基丁烷-2-酮
• 英文名称: 3-bromo-3-phenylbutan-2-one
• CAS: 35307-29-0
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: JBNAKWDVSNSSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-溴-3-苯基丁烷-2-酮 在 三乙烯二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以48%的产率得到3-苯基-3-丁烯-2-酮
  参考文献：
  名称：

  Destabilized carbenium ions. Secondary and tertiary α-acetylbenzyl cations and α-benzoylbenzyl cations

  摘要：

  AbstractThe secondary α‐acetylbenzyl and α‐benzoylbenzyl cations, as well as their tertiary analogues, have been generated in a mass spectrometer by electron impact induced fragmentation of the corresponding α‐bromoketones. These ions belong to the interesting family of destabilized α‐acylcarbenium ions. While primary α‐acylcarbenium ions appear to be unstable, the secondary and tertiaiy ions exhibit the usual behaviour of stable entities in a potential energy well. This can be attributed to a ‘push‐pull’ substitution at the carbenium ion centre by an electron‐releasing phenyl group and an electron‐withdrawing acyl substituent. The characteristic unimolecular reaction of the metastaible secondary and tertiary α‐acylbenzyl cations is the elimination of CO by a rearrangement reaction involving a 1,2‐shift of a methyl group and a phenyl group, respectively. The loss of CO is accompanied by a very large kinetic energy release, which gives rise to broad and dish‐topped peaks for this process in the mass‐analysed ion kinetic energy spectra of the corresponding ions. This behaviour is attributed to the rigid critical configuration of a corner‐protonatei cyclopropanone derivative and a bridged phenonium ion derivative, respectively, for this reaction. For the tertiary α‐acetyl‐α‐methylbenzyl cations, it has been shown by deuterium labelling and by comparison of collisional activation spectra that these ions equilibrate prior to decomposition with their ‘protomer’ derivatives formed by proton migration from the α‐methyl substituent to the carbonyl group and to the benzene ring.

  DOI：

  10.1002/oms.1210220710
• 作为产物：
  描述：

  3-苯基-2-丁酮 在 三氯化铝 溴 作用下， 以 乙醚 为溶剂， 以95%的产率得到3-溴-3-苯基丁烷-2-酮
  参考文献：
  名称：

  Destabilized carbenium ions. Secondary and tertiary α-acetylbenzyl cations and α-benzoylbenzyl cations

  摘要：

  AbstractThe secondary α‐acetylbenzyl and α‐benzoylbenzyl cations, as well as their tertiary analogues, have been generated in a mass spectrometer by electron impact induced fragmentation of the corresponding α‐bromoketones. These ions belong to the interesting family of destabilized α‐acylcarbenium ions. While primary α‐acylcarbenium ions appear to be unstable, the secondary and tertiaiy ions exhibit the usual behaviour of stable entities in a potential energy well. This can be attributed to a ‘push‐pull’ substitution at the carbenium ion centre by an electron‐releasing phenyl group and an electron‐withdrawing acyl substituent. The characteristic unimolecular reaction of the metastaible secondary and tertiary α‐acylbenzyl cations is the elimination of CO by a rearrangement reaction involving a 1,2‐shift of a methyl group and a phenyl group, respectively. The loss of CO is accompanied by a very large kinetic energy release, which gives rise to broad and dish‐topped peaks for this process in the mass‐analysed ion kinetic energy spectra of the corresponding ions. This behaviour is attributed to the rigid critical configuration of a corner‐protonatei cyclopropanone derivative and a bridged phenonium ion derivative, respectively, for this reaction. For the tertiary α‐acetyl‐α‐methylbenzyl cations, it has been shown by deuterium labelling and by comparison of collisional activation spectra that these ions equilibrate prior to decomposition with their ‘protomer’ derivatives formed by proton migration from the α‐methyl substituent to the carbonyl group and to the benzene ring.

  DOI：

  10.1002/oms.1210220710

文献信息

• Boron Trifluoride Mediated Allylation of Aromatic α-Bromoketones by Allyltributyltin
  作者：Hideyoshi Miyake、Ryo Hirai、Yoshie Nakajima、Mitsuru Sasaki

  DOI：10.1246/cl.2003.164

  日期：2003.2

  Replacement of bromine atom of aromatic α-brormoketones by allyltributyltin in the presence of BF3 was described. The reaction proceeds with or without migration of the aryl group, depending on the structure of the α-bromoketone.

  描述了在BF3存在下，用烯丙基三丁基锡替换芳香族α-溴酮的溴原子。反应的进行是否伴随芳基团的迁移，取决于α-溴酮的结构。
• SETIABUDI, FRANS;OESCH, FRANZ;PLATT, KARL L., J. LABELL. COMPOUNDS AND RADIOPHARM., 25,(1988) N 11, C. 1209-1217
  作者：SETIABUDI, FRANS、OESCH, FRANZ、PLATT, KARL L.

  DOI：——

  日期：——
• Destabilized carbenium ions. Secondary and tertiary α-acetylbenzyl cations and α-benzoylbenzyl cations
  作者：Anne-Marie Dommröse、Hans-Friedrich Grützmacher

  DOI：10.1002/oms.1210220710

  日期：1987.7

  AbstractThe secondary α‐acetylbenzyl and α‐benzoylbenzyl cations, as well as their tertiary analogues, have been generated in a mass spectrometer by electron impact induced fragmentation of the corresponding α‐bromoketones. These ions belong to the interesting family of destabilized α‐acylcarbenium ions. While primary α‐acylcarbenium ions appear to be unstable, the secondary and tertiaiy ions exhibit the usual behaviour of stable entities in a potential energy well. This can be attributed to a ‘push‐pull’ substitution at the carbenium ion centre by an electron‐releasing phenyl group and an electron‐withdrawing acyl substituent. The characteristic unimolecular reaction of the metastaible secondary and tertiary α‐acylbenzyl cations is the elimination of CO by a rearrangement reaction involving a 1,2‐shift of a methyl group and a phenyl group, respectively. The loss of CO is accompanied by a very large kinetic energy release, which gives rise to broad and dish‐topped peaks for this process in the mass‐analysed ion kinetic energy spectra of the corresponding ions. This behaviour is attributed to the rigid critical configuration of a corner‐protonatei cyclopropanone derivative and a bridged phenonium ion derivative, respectively, for this reaction. For the tertiary α‐acetyl‐α‐methylbenzyl cations, it has been shown by deuterium labelling and by comparison of collisional activation spectra that these ions equilibrate prior to decomposition with their ‘protomer’ derivatives formed by proton migration from the α‐methyl substituent to the carbonyl group and to the benzene ring.