6-Methyl-4-phenyl-5-hepten-2-one

• 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: 6-Methyl-4-phenyl-5-hepten-2-one
• 英文别名: 6-Methyl-4-phenylhept-5-en-2-one
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: QIUISMLQRXBQEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-6-甲基-3,5-庚二烯-2-酮 、 四苯硼钠 在 palladium diacetate sodium acetate 、 三氯化锑 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以53%的产率得到6-Methyl-4-phenyl-5-hepten-2-one
  参考文献：
  名称：

  A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)-Catalyzed Conjugate Addition of Aromatics to .alpha.,.beta.-Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids

  摘要：

  A remarkable catalytic effect of antimony(III) chloride is disclosed in palladium(0)-catalyzed conjugate addition of aromatics to alpha,beta-unsaturated ketones and aldehydes with sodium tetraphenylborate and arylboronic acids in acetic acid at 25 degrees C. Several other metal chlorides such as AlCl3, SnCl4, AsCl3, TiCl4, FeCl3, MoCl5, and CeCl3 are also effective in some cases, but SbCl3 is the salt of choice. Two key steps are proposed for this reaction: one is the oxidative addition of a C-B bond to Pd(0) forming an arylpalladium species, and the other is the formation of an antimony enolate derived from the initial coordination of SbCl3 to the carbonyl oxygen of an organopalladium intermediate.

  DOI：

  10.1021/jo00109a019

文献信息

• Carboncarbon bond formation by reactions of allylic alcohol with enoxysilane in the presence of Ir-complex
  作者：Isamu Matsuda、Shogo Wakamatsu、Ken-ichi Komori、Tatsuya Makino、Kenji Itoh

  DOI：10.1016/s0040-4039(01)02297-3

  日期：2002.2

  Substitution of allylic alcohols to form a carboncarbon bond is accomplished by a simple reaction of the allylic alcohol itself with an enoxysilane, catalyzed by [Ir(cod)(PPh3)2]X which is activated by H2 molecule. The anion part X of the complexes plays an important role to enhance the rate and product yields of the reactions. The efficacy of the catalyst increases with switching X in the order of

  烯丙基醇本身与烯氧基硅烷的简单反应可完成烯丙基醇的取代反应，该反应由[Ir（cod）（PPh 3）2 ] X催化，后者被H 2分子活化。配合物的阴离子部分X在提高反应速率和产物产率方面起着重要作用。的催化剂增加在PF的顺序切换X功效6 -
• A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)-Catalyzed Conjugate Addition of Aromatics to .alpha.,.beta.-Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids
  作者：Chan Sik Cho、Shin-ichi Motofusa、Kouichi Ohe、Sakae Uemura、Sang Chul Shim

  DOI：10.1021/jo00109a019

  日期：1995.2

  A remarkable catalytic effect of antimony(III) chloride is disclosed in palladium(0)-catalyzed conjugate addition of aromatics to alpha,beta-unsaturated ketones and aldehydes with sodium tetraphenylborate and arylboronic acids in acetic acid at 25 degrees C. Several other metal chlorides such as AlCl3, SnCl4, AsCl3, TiCl4, FeCl3, MoCl5, and CeCl3 are also effective in some cases, but SbCl3 is the salt of choice. Two key steps are proposed for this reaction: one is the oxidative addition of a C-B bond to Pd(0) forming an arylpalladium species, and the other is the formation of an antimony enolate derived from the initial coordination of SbCl3 to the carbonyl oxygen of an organopalladium intermediate.