(E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one | 120943-79-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one
• 英文别名: (2E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one；(E)-3-phenylprop-2-enoyl tert-butyldimethylsilane；(E)-1-[tert-butyl(dimethyl)silyl]-3-phenylprop-2-en-1-one
• CAS: 120943-79-5
• 化学式: C₁₅H₂₂OSi
• 分子量: 246.425
• InChiKey: COVZEEOOSCWCSH-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one 在 4-二甲氨基吡啶 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes

  摘要：

  A novel silyl group-directed anti-S(N)2' reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes with a TBS or TIPS group gave the anti-S(N)2' product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.080
• 作为产物：
  描述：

  苯甲醛 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.84h， 生成 (E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Lewis酸辅助的光诱导的硅烷与醛之间的分子间偶联：正式的交叉苯偶姻型缩合

  摘要：

  易得的酰基硅烷和醛之间的分子间碳-碳键形成反应是在光辐照条件下借助催化量的路易斯酸实现的。将光化学生成的甲硅烷碳烯亲核加成到醛中，然后进行1,4-甲硅烷基迁移，提供了合成上有用的α-甲硅烷氧基酮。路易斯酸对醛的亲电子活化对于有效地实现该反应非常重要，否则所需偶联产物的收率会大大降低。值得注意的是，在路易斯酸性条件下使用酰基硅烷实现了正式的交叉安息香型交叉反应。这是路易斯化学催化的光化学生成的甲氧卡宾与亲电试剂反应的第一个例子。

  DOI：

  10.1002/chem.201704776

文献信息

• Enantio‐, Regio‐ and Chemoselective Copper‐Catalyzed 1,2‐Hydroborylation of Acylsilanes
  作者：Audric Nagy、Laurent Collard、Kiran Indukuri、Tom Leyssens、Olivier Riant

  DOI：10.1002/chem.201901785

  日期：——

  Enantioselective synthesis of synthetically significant (α‐hydroxyallyl)silanes, (α‐hydroxyaryl)silanes, and (α‐hydroxyalkyl)silanes is reported. The present copper‐catalyzed 1,2‐selective hydroborylation of acylsilanes affords the aforementioned products in high yields and with high enantiomeric excesses. This robust and scalable additive‐free catalytic system relies on the use of low copper(II) acetate

  报道了对合成重要的（α-羟基烯丙基）硅烷，（α-羟基芳基）硅烷和（α-羟基烷基）硅烷的对映选择性合成。目前的铜催化酰基硅烷的1,2-选择加氢硼化可以高收率和高对映体过量提供上述产品。这种强大且可扩展的无添加剂催化体系依赖于在市场上可买到且稳定的氢化物源存在下，在室温下使用低乙酸铜（II）和二膦配体的负载量。
• Comparing α-carbanion-stabilizing ability of substituents using the Brook rearrangement
  作者：Kei Takeda、Haruka Ubayama、Ayako Sano、Eiichi Yoshii、Toru Koizumi

  DOI：10.1016/s0040-4039(98)01032-6

  日期：1998.7

  The α-carbanion-stabilizing ability of the phenylthio and trimethylsilyl groups was compared based on the relative rate of the base-catalyzed Brook rearrangement of the β-substituted α-silylallylalcohol.

  基于β-取代的α-甲硅烷基烯丙基醇的碱催化的布鲁克重排的相对速率，比较了苯硫基和三甲基甲硅烷基的α-碳负离子稳定能力。
• Enantioselective Synthesis of α-Silylamines by Meerwein–Ponndorf–Verley-Type Reduction of α-Silylimines by a Chiral Lithium Amide
  作者：Yasuhiro Kondo、Michiko Sasaki、Masatoshi Kawahata、Kentaro Yamaguchi、Kei Takeda

  DOI：10.1021/jo500441a

  日期：2014.4.18

  Meerwein-Ponndorf-Verley-type reduction of N-tosylsilylimines with chiral lithium amide 2 affords alpha-silylamines in high enantioselectivity. Since the enantioselectivity observed was inconsistent with our previously proposed chairlike six-membered transition structure, we performed density functional theory (DFT) calculations on transition states leading to (S)- and (R)-7a and (S)- and (R)-7e using an N-phenylsulfonyl derivatives 12 and 13 as model systems. Results of the calculations showed that the structures are considerably deformed from the chairlike form with steric repulsions between the 1'-methylene group and the imine-carbon substituents playing an important role in the control of the, enantioselectivity.
• Application of (.alpha.-phosphonoacyl)silane reagents to the synthesis of .alpha.,.beta.-unsaturated acylsilanes
  作者：James S. Nowick、Rick L. Danheiser

  DOI：10.1021/jo00273a007

  日期：1989.6
• Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity
  作者：Pascale Doussot、Charles Portella

  DOI：10.1021/jo00076a029

  日期：1993.11

  1-Alkyl (or aryl)-1-[(trialkylsilyl)oxy]perfluoroalk-1-enes were synthesized from acylsilanes and perfluoroalkyl iodides. Perfluoroorganolithium and magnesium were used for aliphatic and aromatic derivatives, respectively. These enoxysilanes have nucleophilic as well as electrophilic properties. They are enolate equivalents, leading to 2-hydroperfluoroalkyl ketones on hydrolysis, or aldol products. With good nucleophiles like amines, they react as electron poor alkenes to give beta-enamino ketones.