3,3-Dimethyl-2-methylene-1-phenyl-butan-1-one | 112255-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-Dimethyl-2-methylene-1-phenyl-butan-1-one
• 英文别名: 3,3-Dimethyl-2-methylidene-1-phenylbutan-1-one
• CAS: 112255-61-5
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: YAHALYZINVNVAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  3,3-Dimethyl-2-methylene-1-phenyl-butan-1-one 、 烯丙基三甲基硅烷 、 trityl perchlorate 、 2-吡啶甲醇 、 乙腈 以19%的产率得到
  参考文献：
  名称：

  HAYASHI MASAJI; MUKAIYAMA TERUAKI, CHEM. LETT.,(1987) N 2, 289-292

  摘要：

  DOI：
• 作为产物：
  描述：

  α-hydroxy-3,3-dimethyl-2-butyl phenyl ketone 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以78%的产率得到3,3-Dimethyl-2-methylene-1-phenyl-butan-1-one
  参考文献：
  名称：

  Trifluoromethanesulfonic (triflic) acid catalyzed transformations of .alpha.-hydroxy carbonyl compounds

  摘要：

  Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantonone. Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione. Reaction of a series of alpha-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively. The reactions and their suggested mechanism are discussed.

  DOI：

  10.1021/jo00007a048

文献信息

• Synthesis of 2-alkyl (and aryl)-1-aryl-2-propen-1-ones via m-CPBA mediated oxidation of γ-(benzotriazol-1-yl)allylic selenides
  作者：Taehoon Kim、Kyongtae Kim

  DOI：10.1016/s0040-4039(02)00388-x

  日期：2002.4

  Treatment of 2-alkyl (and aryl)-3-aryl-3-(benotriazol-1-yl)allylic selenides with m-CPBA (1 equiv.) for 10 min in Ch(2)Cl(2) at rt gave 2-alkyl (and aryl)-1-aryl-2-propen-1-ones in excellent yields. (C) 2002 Published by Elsevier Science Ltd.
• OLAH, GEORGE A.;WU, AN-HSIANG, J. ORG. CHEM., 56,(1991) N, C. 2531-2534
  作者：OLAH, GEORGE A.、WU, AN-HSIANG

  DOI：——

  日期：——
• HAYASHI MASAJI; MUKAIYAMA TERUAKI, CHEM. LETT.,(1987) N 2, 289-292
  作者：HAYASHI MASAJI、 MUKAIYAMA TERUAKI

  DOI：——

  日期：——
• Trifluoromethanesulfonic (triflic) acid catalyzed transformations of .alpha.-hydroxy carbonyl compounds
  作者：George A. Olah、An Hsiang Wu

  DOI：10.1021/jo00007a048

  日期：1991.3

  Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantonone. Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione. Reaction of a series of alpha-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively. The reactions and their suggested mechanism are discussed.