Benzyl 4-chloro-2-butynyl ether | 775-26-8

• 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: Benzyl 4-chloro-2-butynyl ether
• 英文别名: Benzyl-<4-chlor-butin-(2)-yl>-ether；4-Chlorobut-2-ynoxymethylbenzene；4-chlorobut-2-ynoxymethylbenzene
• CAS: 775-26-8
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: DBNRQQIWACJOHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-氟-1-己醇 、 Benzyl 4-chloro-2-butynyl ether 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 以69%的产率得到Benzyl 4-(6-fluorohexyloxy)-2-butynyl ether
  参考文献：
  名称：

  Preparation of a New Carboranyl Lactoside for the Treatment of Cancer by Boron Neutron Capture Therapy: Synthesis and Toxicity of Fluoro Carboranyl Glycosides for in vivo19F-NMR Spectroscopy

  摘要：

  The synthesis of new ortho-carboranyl lactosides 8, 17, 19 and glucosides 22 and 23 for the use in boron neutron capture therapy is reported. Carboranyl lactosides 17 and 19 as well as the glucosides 22 and 23 contain a fluorine atom to allow a noninvasive determination of these compounds in tumor cells by F-19-NMR spectroscopy. In cloning efficiency tests on human bronchial carcinoma cells the carboranyl lactosides 17 and 19 displayed almost no cytotoxicity. Thus, the considerably cytotoxic carboranyl alcohol 11 is detoxified when linked to a sugar moiety such as in carboranyl glucoside 22.

  DOI：

  10.1002/(sici)1521-3765(20000303)6:5<836::aid-chem836>3.0.co;2-8
• 作为产物：
  描述：

  4-benzyloxy-2-butyn-1-ol 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到Benzyl 4-chloro-2-butynyl ether
  参考文献：
  名称：

  Preparation of a New Carboranyl Lactoside for the Treatment of Cancer by Boron Neutron Capture Therapy: Synthesis and Toxicity of Fluoro Carboranyl Glycosides for in vivo19F-NMR Spectroscopy

  摘要：

  The synthesis of new ortho-carboranyl lactosides 8, 17, 19 and glucosides 22 and 23 for the use in boron neutron capture therapy is reported. Carboranyl lactosides 17 and 19 as well as the glucosides 22 and 23 contain a fluorine atom to allow a noninvasive determination of these compounds in tumor cells by F-19-NMR spectroscopy. In cloning efficiency tests on human bronchial carcinoma cells the carboranyl lactosides 17 and 19 displayed almost no cytotoxicity. Thus, the considerably cytotoxic carboranyl alcohol 11 is detoxified when linked to a sugar moiety such as in carboranyl glucoside 22.

  DOI：

  10.1002/(sici)1521-3765(20000303)6:5<836::aid-chem836>3.0.co;2-8

文献信息

• Palladium Pincer Complex Catalyzed Stannyl and Silyl Transfer to Propargylic Substrates:  Synthetic Scope and Mechanism
  作者：Johan Kjellgren、Henrik Sundén、Kálmán J. Szabó

  DOI：10.1021/ja043951b

  日期：2005.2.1

  corresponding pincer complex catalyst. DFT modeling studies have shown that the trimethylstannyl functionality is transferred to the propargylic substrate in a single reaction step with high allenyl selectivity. Inspection of the TS structures reveals that the trimethylstannyl group transfer is initiated by the attack of the palladium-tin sigma-bond electrons on the propargylic substrate. This is a novel

  使用基于锡和硅的双金属试剂可以实现钳形配合物催化取代各种炔丙基底物，以获得炔丙基和烯丙基锡烷和硅烷。这些涉及氯化物、甲磺酸盐和环氧化物底物的反应可以在温和的条件下进行，因此可以耐受许多官能团（如 COOEt、OR、OH、NR 和 NAc）。结果表明，带有供电子配体的钳形催化剂，如 NCN、SCS 和 SeCSe 配合物，显示出最高的催化活性。具有吸电子取代基的仲炔丙基氯和伯炔丙基氯的催化取代以高区域选择性进行，提供了丙二烯基产物。炔丙基环氧化物的开环具有优异的立体选择性和区域选择性，得到立体确定的烯基锡烷。甲硅烷基锡烷作为双金属试剂进行独家甲硅烷基转移到炔丙基底物，提供具有高区域选择性的丙二烯基硅烷。根据我们的机理研究，反应的关键中间体是有机锡烷（或硅烷）配位的钳形配合物，它由双金属试剂和相应的钳形配合物催化剂形成。DFT 建模研究表明，三甲基甲锡烷基官能团在单个反应步骤中以高烯丙基选择性转移到炔丙基底物上。对