2-(4-chlorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol | 1312791-27-7

• 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: 2-(4-chlorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol
• 英文别名: 2-(4-Chlorophenyl)-5-trimethylsilylpent-4-yn-2-ol；2-(4-chlorophenyl)-5-trimethylsilylpent-4-yn-2-ol
• CAS: 1312791-27-7
• 化学式: C₁₄H₁₉ClOSi
• 分子量: 266.843
• InChiKey: FKYRVCQSIWLKOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol 在 potassium carbonate 、 水 作用下， 以 甲醇 、 醋酸异丙酯 为溶剂， 反应 1.0h， 以1.83 g的产率得到2-(4-chlorophenyl)pent-4-yn-2-ol
  参考文献：
  名称：

  Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

  摘要：

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

  DOI：

  10.1021/ol902457m
• 作为产物：
  描述：

  trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 、 对氯苯乙酮 在 MeO-BIBOP 、 silver trifluoromethanesulfonate 、 lithium tert-butoxide 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-(4-chlorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol
  参考文献：
  名称：

  A General Copper–BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates

  摘要：

  An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.

  DOI：

  10.1021/ja2028958

文献信息

• A General Copper–BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates
  作者：Keith R. Fandrick、Daniel R. Fandrick、Jonathan T. Reeves、Joe Gao、Shengli Ma、Wenjie Li、Heewon Lee、Nelu Grinberg、Bruce Lu、Chris H. Senanayake

  DOI：10.1021/ja2028958

  日期：2011.7.13

  An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.
• Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates
  作者：Daniel R. Fandrick、Keith R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Courtney S. Johnson、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol902457m

  日期：2010.1.1

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.
• Copper-Catalyst-Controlled Site-Selective Allenylation of Ketones and Aldehydes with Propargyl Boronates
  作者：Keith R. Fandrick、Junichi Ogikubo、Daniel R. Fandrick、Nitinchandra D. Patel、Jaideep Saha、Heewon Lee、Shengli Ma、Nelu Grinberg、Carl A. Busacca、Chris H. Senanayake

  DOI：10.1021/ol400124f

  日期：2013.3.15

  A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown to direct the site selectivity for which either propargyl or allenyl adducts can be acquired in high selectivity. A model is proposed that explains the origin of the site selectivity.