3-methoxy-2-[2-(triethoxysilyl)ethyl]acetophenone | 173098-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-2-[2-(triethoxysilyl)ethyl]acetophenone
• 英文别名: 1-[3-methoxy-(2-(2-triethoxysilyl)ethyl)phenyl]ethanone；1-[3-Methoxy-2-(2-triethoxysilylethyl)phenyl]ethanone；1-[3-methoxy-2-(2-triethoxysilylethyl)phenyl]ethanone
• CAS: 173098-27-6
• 化学式: C₁₇H₂₈O₅Si
• 分子量: 340.492
• InChiKey: ZAYWQMGFDPVBNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙烯基三乙氧基硅烷 、 3-甲氧基苯乙酮 在 rhodium(III) chloride hydrate 、 sodium formate 、 三(4-三氟甲苯基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以83%的产率得到3-methoxy-2-[2-(triethoxysilyl)ethyl]acetophenone
  参考文献：
  名称：

  Ruthenium Chloride as an Efficient Catalytic Precursor for Hydroarylation Reactions via C−H bond Activation

  摘要：

  A very simple and efficient catalytic system for the hydroarylation of olefins by aromatic ketones and Michael acceptors using simple and inexpensive ruthenium trichloride as a ruthenium source is described. These very mild conditions (dioxane at 80 C) appeared to be highly compatible, tolerant, and selective toward various functional groups, and the ease of the protocol is highly convenient for synthetic purposes.

  DOI：

  10.1021/ol101038c

文献信息

• Ruthenium-Catalyzed Addition of Carbon–Hydrogen Bonds in Aromatic Ketones to Olefins. The Effect of Various Substituents at the Aromatic Ring
  作者：Motohiro Sonoda、Fumitoshi Kakiuchi、Naoto Chatani、Shinji Murai

  DOI：10.1246/bcsj.70.3117

  日期：1997.12

  To obtain further insight into the new ruthenium-catalyzed reaction of carbon–hydrogen bonds in aromatic ketones with olefins, the effect of various substituents at the aromatic ring is examined. Reaction of o-methylacetophenone with triethoxyvinylsilane (2) in the presence of [Ru(H)2(CO)(PPh3)3] (3)as the catalyst gave the 1 : 1 addition product in quantitative yield. Similarly, the ketone having

  为了进一步了解钌催化芳香酮中碳氢键与烯烃的新反应，研究了芳香环上各种取代基的影响。在作为催化剂的[Ru(H)2(CO)(PPh3)3](3)存在下，邻甲基苯乙酮与三乙氧基乙烯基硅烷(2)的反应以定量收率得到1:1的加成产物。类似地，具有o-CF3基团的酮以92%的产率得到偶联产物9。然而，邻位取代基如 OMe、F 和 CN 似乎会与催化剂反应并杀死催化剂，因此无法实现有效的反应。在对甲氧基和对氟苯乙酮与 2 反应的情况下，得到相应的 1:2 加成产物作为主要产物。在 m-取代的苯乙酮的情况下，邻位有两个不同的 C-H 键。C-C 键的形成优先发生在空间上不太拥挤的位置。间甲氧基和间氟苯乙酮的反应除外，...
• C−C Bond Formation via C−H Bond Activation Under Protic Conditions: On the Role of Phosphane Ligand and Cosolvent
  作者：Marc-Olivier Simon、Rémi Martinez、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/jo902264u

  日期：2010.1.1

  Effective conditions for the hydroarylation of vinylsilanes, allowing functionalization of various aromatic ketones in good yields at low temperature, using isopropanol, a protic solvent, are reported. Moreover, conducting this C−C bond-forming reaction under conditions similar to those used for hydride transfer reduction, the reduction of the ketone could be suppressed, simply by using acetone cosolvent

  据报道，使用质子溶剂异丙醇，乙烯基硅烷的氢芳基化的有效条件允许在低温下以良好的产率官能化各种芳族酮。而且，在类似于用于氢化物转移还原的条件下进行该CC键形成反应，仅通过使用丙酮助溶剂作为氢化物受体，就可以抑制酮的还原。用廉价且无毒的溶剂进行的该反应在质子条件下用低价钌络合物构成了第一个C（sp 2）-H活化。
• Directing effect of functional groups in ruthenium-catalyzed addition of substituted acetophonones to an olefin
  作者：Motohiro Sonoda、Fumitoshi Kakiuchi、Naoto Chatani、Shinji Murai

  DOI：10.1016/0022-328x(95)05607-q

  日期：1995.11

  Ruthenium-catalyzed addition of 3′-methyl-, 3′-trifluoromethyl-, and 3′-N,N-dimethylaminoacetophenones to an olefin proceeds site selectively at 6′ CH bonds to give the 1:1 CH/olefin addition products in high yields. In contrast, the addition of 3′-methoxyacetophenone takes place preferentially at the CH bond at the more congested 2′ position.

  钌催化的3'-甲基-，3'-三氟甲基-和3'- N，N-二甲基氨基苯乙酮向烯烃的加成选择性地在6'C siteH键处进行，从而得到1：1CH/烯烃高产的加成产品。相反，3'-甲氧基苯乙酮的添加优先在更拥挤的2'位置的CH键处发生。
• Martinez, Remi; Simon, Marc-Olivier; Chevalier, Reynald, Journal of the American Chemical Society, 2009, vol. 131, p. 7887 - 7895
  作者：Martinez, Remi、Simon, Marc-Olivier、Chevalier, Reynald、Pautigny, Cyrielle、Genet, Jean-Pierre、Darses, Sylvain

  DOI：——

  日期：——
• Ruthenium Chloride as an Efficient Catalytic Precursor for Hydroarylation Reactions via C−H bond Activation
  作者：Marc-Olivier Simon、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/ol101038c

  日期：2010.7.2

  A very simple and efficient catalytic system for the hydroarylation of olefins by aromatic ketones and Michael acceptors using simple and inexpensive ruthenium trichloride as a ruthenium source is described. These very mild conditions (dioxane at 80 C) appeared to be highly compatible, tolerant, and selective toward various functional groups, and the ease of the protocol is highly convenient for synthetic purposes.