1-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one | 905266-48-0

• 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: 1-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one
• 英文别名: 1-[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-en-1-one；1-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-en-1-one
• CAS: 905266-48-0
• 化学式: C₁₅H₂₂O₂Si
• 分子量: 262.424
• InChiKey: OXMSJFZZIXCHET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one 在 dimethyl sulfide borane 、 (R)-oxazaborolidine 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(S)-4-O-tert-butyldimethylsilyl-1'-hydroxychavicol
  参考文献：
  名称：

  New Rev-export inhibitor from Alpinia galanga and structure–activity relationship

  摘要：

  Bioassay-guided separation by use of the fission yeast expressing NES of Rev, an HIV-1 viral regulatory protein, disclosed 1'-acetoxychavicol acetate (ACA, 1) as a new inhibitor for nuclear export of Rev from the roots of Alpinia galanga. Both analysis for mechanism of action with biotinylated probe ( 2) and several synthesized analogs established crucial portions in 1 for Rev-export inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.047
• 作为产物：
  描述：

  1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  New Rev-export inhibitor from Alpinia galanga and structure–activity relationship

  摘要：

  Bioassay-guided separation by use of the fission yeast expressing NES of Rev, an HIV-1 viral regulatory protein, disclosed 1'-acetoxychavicol acetate (ACA, 1) as a new inhibitor for nuclear export of Rev from the roots of Alpinia galanga. Both analysis for mechanism of action with biotinylated probe ( 2) and several synthesized analogs established crucial portions in 1 for Rev-export inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.047

文献信息

• Oxovanadium(v)-induced diastereoselective oxidative homocoupling of boron enolates
  作者：Toru Amaya、Takaya Masuda、Yusuke Maegawa、Toshikazu Hirao

  DOI：10.1039/c3cc49624d

  日期：——

  Oxovanadium(v)-induced dl-selective oxidative coupling of (Z)-boron enolate was demonstrated to give the corresponding 2,3-disubstituted 1,4-diketone in a good yield. High selectivity (up to 94 : 6) was attained when the reaction was performed with VO(OPr-i)2Cl at -30 degrees C.

  氧杂钒（v）诱导的（Z）-硼烯醇化物的dl-选择性​​氧化偶联被证明以良好的产率得到了相应的2,3-二取代的1,4-二酮。当与VO（OPr-i）2Cl在-30摄氏度下进行反应时，可获得高选择性（高达94：6）。
• Stereoselective Synthesis of Silyl Enol Ethers with Acylsilanes and α,β-Unsaturated Ketones
  作者：Ying Liu、Zhihong Zhu、Yunxiao Zhang、Yizhi Zhang、Shanshan Liu、Xiao Shen

  DOI：10.1021/acs.orglett.4c01782

  日期：2024.7.19

  emerging bench-stable reagents for the generation of electron-rich oxycarbenes that are difficult to access with unstable diazo compounds. Herein, we report a siloxycarbene-mediated stereoselective synthesis of silyl enol ethers through visible-light-induced intermolecular reactions between acylsilanes and α,β-unsaturated ketones. Both the solvent and low temperature are important for the success of the

  酰基硅烷是新兴的实验室稳定试剂，用于生成富电子的氧卡宾，而不稳定的重氮化合物难以获得这些氧卡宾。在此，我们报道了通过可见光诱导酰基硅烷和α,β-不饱和酮之间的分子间反应，硅氧卡宾介导的硅烯醇醚的立体选择性合成。溶剂和低温对于反应的成功都很重要。这种方法具有原子经济学、独特的立体控制和广泛的底物范围。该方法的合成潜力通过克级反应和各种下游转化（包括要求硅烯醇醚构型纯度的转化）得到证明。
• A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps
  作者：Gullapalli Kumaraswamy、Dasa Rambabu

  DOI：10.1016/j.tetasy.2013.01.005

  日期：2013.2

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.