2-methyl-2-(4-phenylbut-1-yn-1-yl)oxirane | 1191988-20-1

• 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-methyl-2-(4-phenylbut-1-yn-1-yl)oxirane
• 英文别名: 2-Methyl-2-(4-phenylbut-1-ynyl)oxirane
• CAS: 1191988-20-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: ZBKRJFGOVIVJTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(4-phenylbut-1-yn-1-yl)oxirane 在 三苯基膦氯金 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以26%的产率得到2-phenethyl-4-methylfuran
  参考文献：
  名称：

  Cationic Gold(I)-Mediated Intramolecular Cyclization of 3-Alkyne-1,2-diols and 1-Amino-3-alkyn-2-ols: A Practical Route to Furans and Pyrroles

  摘要：

  The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amino-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph3P)AuCl-AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles in excellent yields (85-98% yields). This method is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.

  DOI：

  10.1021/ol901942t
• 作为产物：
  描述：

  4-苯基-1-丁炔 、 一氯丙酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.5h， 以65%的产率得到2-methyl-2-(4-phenylbut-1-yn-1-yl)oxirane
  参考文献：
  名称：

  Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

  摘要：

  Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S(N)2' pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

  DOI：

  10.1021/ja502792s

文献信息

• Copper‐Mediated Dichotomic Borylation of Alkyne Carbonates: Stereoselective Access to ( <i>E</i> )‐1,2‐Diborylated 1,3‐Dienes versus Traceless Monoborylation Affording α‐Hydroxyallenes
  作者：Kun Guo、Arjan W. Kleij

  DOI：10.1002/anie.202014310

  日期：2021.2.23

  A mild copper‐mediated protocol has been developed for borylation of alkynyl cyclic carbonates. Depending on the nature of the borylating reaction partner, either stereoselective diborylation of the propargylic surrogate takes place, providing convenient access to (E)‐1,2‐borylated 1,3‐dienes, or traceless monoborylation occurs, which leads to α‐hydroxyallenes as the principal product. The dichotomy

  已经开发了一种温和的铜介导方案，用于炔基环状碳酸酯的硼酸酯化。取决于硼化反应伙伴的性质，发生炔丙基替代物的立体选择性二硼基化，提供与（E）-1,2-硼基化的1,3-二烯的便捷连接，或者发生无痕的单硼化，从而导致α-羟基丙二烯作为主要产品。该硼化方案的二分法已通过多个对照实验进行了详细研究，表明diboron（4）试剂的相对较小变化允许在环境条件下竞争性的醇辅助原金属脱除而伪造出α-羟基丙二烯产物。
• Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates
  作者：Jian Zhao、Kálmán J. Szabó

  DOI：10.1002/anie.201510132

  日期：2016.1.22

  A new copper-catalyzed reaction for the stereo- and regioselective synthesis of alkenyl diboronates and allenyl boronates is presented. In this process propargyl derivatives of strained three/four-membered rings were employed as substrates and B2pin2 was used as the boronate source. Selective formation of the alkenyl diboronate versus the allenyl boronate products was controlled by the choice of phosphine

  提出了新的铜催化的链烯基二硼酸酯和烯基硼酸酯的立体和区域选择性合成反应。在该方法中，将应变的三元/四元环的炔丙基衍生物用作底物，并将B2pin2用作硼酸盐源。通过选择膦配体来控制烯基二硼酸酯相对于烯基硼酸酯产物的选择性形成。