1-(2-tert-butyldimethylsilyloxy)phenyl-3-phenyl-2-propyn-1-one | 223511-19-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-tert-butyldimethylsilyloxy)phenyl-3-phenyl-2-propyn-1-one
• 英文别名: 1-[2-(tert-butyldimethylsilyloxy)phenyl]-3-phenylprop-2-yn-1-one；1-[2-[Tert-butyl(dimethyl)silyl]oxyphenyl]-3-phenylprop-2-yn-1-one
• CAS: 223511-19-1
• 化学式: C₂₁H₂₄O₂Si
• 分子量: 336.506
• InChiKey: XTUXYIPYYXBNAA-UHFFFAOYSA-N

物化性质

• 沸点：
  414.1±47.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butyldimethylsilyloxy)phenyl-3-phenyl-2-propyn-1-one 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以96%的产率得到黄酮
  参考文献：
  名称：

  Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries

  摘要：

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00279-8
• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-((tert-butyldimethylsilyl)oxy)benzoate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 1-(2-tert-butyldimethylsilyloxy)phenyl-3-phenyl-2-propyn-1-one
  参考文献：
  名称：

  Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries

  摘要：

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00279-8

文献信息

• Synthesis of 3-Halogenated Flavonoids<i>via</i>Electrophile-Promoted Cyclization of 2-(3-Aryl-2-propynoyl)anisoles
  作者：Chi-Fong Lin、Tsai-Hui Duh、Wen-Der Lu、Jeng-Lin Lee、Chia-Ying Lee、Chin-Chau Chen、Ming-Jung Wu

  DOI：10.1002/jccs.200400027

  日期：2004.2

  Treatment of 2-(1-aryl-3-propynoyl) anisoles 1 with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) gave the 3-halogenated flavones and their related molecules in moderate yields.

  用 N-氯代琥珀酰亚胺 (NCS) 或 N-溴代琥珀酰亚胺 (NBS) 处理 2-(1-aryl-3-propynoyl) 苯甲醚 1 以中等收率得到 3-卤代黄酮及其相关分子。
• Synthesis of 2-(Diarylmethylene)-3-benzofuranones Promoted via Palladium-Catalyzed Reactions of Aryl iodides with 3-Aryl-1-(2-<i>tert</i>-butyldimethyl­silyloxy)phenyl-2-propyn-1-ones
  作者：Ming-Jung Wu、Chi-Fong Lin、Wen-Der Lu、I-Wen Wang

  DOI：10.1055/s-2003-42049

  日期：——

  3-Substituted-1-(2-tert-butyldimethylsilyloxy)phenyl-2-propyn-1-ones were coupled with aryl iodides by using palladium as a catalyst in ambient MeOH solution and gave 2-(diarylmethylene)-3-benzofuranones in moderate to good yields.

  3-取代-1-(2-叔丁基二甲基硅氧基)苯基-2-丙炔-1-酮与芳基碘化物在常温甲醇溶液中通过钯催化偶联反应，获得了中等至良好的产率的2-(二芳甲烯)-3-苯并呋喃酮。
• Synthesis of 1,3-thioxoketones from salicylaldehyde
  作者：I. S. Semenova、V. N. Yarovenko、K. S. Levchenko、M. M. Krayushkin

  DOI：10.1007/s11172-013-0135-9

  日期：2013.4

  A method for the synthesis of monothiodibenzoylmethanes was developed. The method involves a reaction of potassium thioacetate with 1-(2-hydroxyphenyl)-3-phenylpropynone prepared from salicylaldehyde.

  开发了一种合成单硫代二苯甲酰甲烷的方法。该方法涉及硫代乙酸钾与由水杨醛制备的 1-(2-羟基苯基)-3-苯基丙炔酮的反应。
• Novel synthetic routes suitable for constructing benzopyrone combinatorial libraries
  作者：Abhijit S. Bhat、Jennifer L. Whetstone、Robert W. Brueggemeier

  DOI：10.1016/s0040-4039(99)00279-8

  日期：1999.3

  A series of O-(t-butylsilyloxy)benzoyl chlorides generated from the corresponding silyl esters were coupled with a range of terminal alkynes to afford the corresponding alkynyl ketones. The alkynyl ketones were converted to enaminoketones and then cyclized to yield the desired benzopyrone ring system. This synthetic protocol utilizes readily available starting materials, mild and high yielding reactions with good functional group tolerance, and is ideal for developing combinatorial libraries centered around the benzopyrone ring system. (C) 1999 Elsevier Science Ltd. All rights reserved.