1-(3-bromophenyl)prop-2-yn-1-ol | 29805-16-1

• 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: 1-(3-bromophenyl)prop-2-yn-1-ol
• 英文别名: 1-(3-Bromophenyl)-2-propyn-1-ol
• CAS: 29805-16-1
• 化学式: C₉H₇BrO
• 分子量: 211.058
• InChiKey: VLPLERWMKJHACA-UHFFFAOYSA-N

物化性质

• 沸点：
  276.4±25.0 °C(Predicted)
• 密度：
  1.541±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1-(3-bromophenyl)prop-2-yn-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以79%的产率得到3-bromo-1-(3-bromophenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction

  摘要：

  A mild, cascade methodology based on the modified Cadiot-Chodkiewicz reaction was developed for the stereoselective synthesis of trans-enynones. By this methodology, structurally divergent trans-enynones, which are embedded with sensitive functional groups, were synthesized. Control experiments suggested that the CuCl alone does not have a role in the isomerization step, whereas the CuCl piperidine complex (formed during the cross coupling) may have a rate enhancing effect. Furthermore, additional sets of control experiments favor the involvement of unimolecular [1,2]-H shift rather than a homobimolecular proton abstraction during the isomerization step.

  DOI：

  10.1021/acs.joc.5b01780
• 作为产物：
  描述：

  4-(3-bromophenyl)-4-hydroxybut-2-ynoic acid 在 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到1-(3-bromophenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Catalytic Decarboxylation of 2-Alkynoic Acids

  摘要：

  A very efficient protocol enabling catalytic decarboxylation of a wide range of 2-alkynoic acids is described. The reaction conditions and the scope of the process are examined. The method is further utilized in a model decarboxylative coupling.

  DOI：

  10.1021/jo901377b

文献信息

• Gold(I)-Catalyzed Decarboxylation of Propargyl Carbonates: Reactivity Reversal of the Gold Catalyst from<i>π</i>-Lewis Acidity to<i>σ</i>-Lewis Acidity
  作者：Ruwei Shen、Jianjun Yang、Shugao Zhu、Chao Chen、Luling Wu

  DOI：10.1002/adsc.201401094

  日期：2015.4.13

  A cationic gold(I)‐catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct σ‐Lewis acidity rather than the commonly observed π‐Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This

  据报道，阳离子金（I）催化炔丙基碳酸酯的脱羧醚化反应以选择性地产生炔丙基醚。在该反应中，金（I）催化剂显示出明显的σ-路易斯酸度，而不是通常观察到的π-路易斯酸度，因此催化了各种炔丙基碳酸酯的脱羧反应，从而提供了具有高选择性的相应炔丙基醚。该反应代表了σ-刘易斯酸度和π-刘易斯酸度之间阳离子金（I）配合物的可调反应性的罕见例子。
• A bifunctional ligand enables efficient gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids
  作者：Shengrong Liao、Huayan Xu、Liang Xu、Baoxia Liang、Bin Yang、Junfeng Wang、Xuefeng Zhou、Xiuping Lin、Zaigang Luo、Yonghong Liu

  DOI：10.1016/j.tet.2020.131764

  日期：2021.1

  Terminal allylic alcohols are important motifs in natural products, and also key intermediates/precursors in numerous novel reaction transformations. In this study, enabled by a bifunctional ligand featuring a basic amino group, a gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids has been first established, and efficiently affords various terminal

  末端烯丙醇是天然产物中的重要基序，也是许多新颖反应转化中的关键中间体/前体。在这项研究中，通过具有碱性氨基的双功能配体，首先建立了末端未活化的炔丙醇与杂芳烃硼酸的金催化加氢芳基化反应，并能在温和的条件下以中等至高收率有效地提供各种末端芳基取代的烯丙基醇。条件。
• Direct synthesis of pyrroles via 1,3-dipolar cycloaddition of azomethine ylides with ynones
  作者：Zheng Wang、Ying Shi、Xiaoyan Luo、De-Man Han、Wei-Ping Deng

  DOI：10.1039/c3nj00067b

  日期：——

  A direct and facile synthesis of multi-substituted pyrroles via AgOAc-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with ynones is developed, providing the corresponding adducts in moderate to high yields (up to 89%).

  已开发了通过AgOAc催化的偶氮甲亚胺与炔酮的1,3-偶极环加成反应直接合成多取代吡咯的方法，可提供中等至高收率（最高89％）的相应加合物。
• Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes
  作者：Brett R. Ambler、Santosh Peddi、Ryan A. Altman

  DOI：10.1021/acs.orglett.5b01027

  日期：2015.5.15

  report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-

  历史上，“ Cu–CF 3 ”物种已用于广泛的亲核三氟甲基化反应。尽管最近的进展已经使用了配体来稳定和利用这一关键有机金属中间体的反应性，但是配体区分Cu–CF 3的区域化学结果的能力以前尚未报道过介导或催化的反应。在此，我们报道了一个铜催化的三氟甲基化反应的第一个例子，其中配体控制了区域化学结果。更具体地说，我们证明了联吡啶基配体控制铜催化的炔丙基亲电子的亲核三氟甲基化反应生成（三氟甲基）丙二烯的区域选择性的能力。该方法提供了各种二，三和四取代的（三氟甲基）亚芳基，可以对其进行进一步修饰以生成复杂的氟化亚结构。
• Ruthenium-Catalyzed Propargylic Reduction of Propargylic Alcohols with Hantzsch Ester
  作者：Haowei Ding、Ken Sakata、Shogo Kuriyama、Yoshiaki Nishibayashi

  DOI：10.1021/acs.organomet.0c00187

  日期：2020.6.8

  Ruthenium-catalyzed propargylic reduction of propargylic alcohols bearing a terminal alkyne moiety is accomplished by using Hantzsch ester as a nucleophilic hydride source. A variety of secondary and tertiary propargylic alcohols are reduced to the corresponding propargylic reduced products such as 1-alkynes in excellent yields. Some mechanistic studies indicate that ruthenium–allenylidene complexes

  钌催化的带有末端炔烃部分的炔丙醇的炔丙基还原是通过使用Hantzsch酯作为亲核氢化物源来完成的。各种仲和叔炔丙醇以优异的产率还原为相应的炔丙基还原产物，例如1-炔烃。一些机理研究表明，钌-亚烯基络合物可能是关键的反应中间体。