5-hydroxy-5-methyl-1-phenylhept-1,3-diyne | 92495-62-0

• 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: 5-hydroxy-5-methyl-1-phenylhept-1,3-diyne
• 英文别名: 3-Methyl-7-phenylhepta-4,6-diyn-3-ol
• CAS: 92495-62-0
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: KOCPOPUIVPCRLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5-hydroxy-5-methyl-1-phenylhept-1,3-diyne 在 二氧化碳 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 90.0 ℃ 、2.0 MPa 条件下， 反应 36.0h， 以81%的产率得到5-benzyl-2-ethyl-2-methylfuran-3(2H)-one
  参考文献：
  名称：

  Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols

  摘要：

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.130
• 作为产物：
  描述：

  苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 silver nitrate 、 正丁胺 、 copper(l) chloride 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 5-hydroxy-5-methyl-1-phenylhept-1,3-diyne
  参考文献：
  名称：

  Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols

  摘要：

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.130

文献信息

• Computer-Assisted Design of Ionic Liquids for Efficient Synthesis of 3(2<i>H</i>)-Furanones: A Domino Reaction Triggered by CO₂
  作者：Kaihong Chen、Guiling Shi、Weidong Zhang、Haoran Li、Congmin Wang

  DOI：10.1021/jacs.6b08895

  日期：2016.11.2

  A strategy for the highly efficient synthesis of 3(2H)-furanones by hydration of diyne alcohols catalyzed by base-functionalized ionic liquids under atmospheric-pressure CO2 that was developed through computer-assisted design is reported. The best range of basic ionic liquids as catalysts was predicted at first, and [HDBU][BenIm] exhibited the highest catalytic activity. Through a combination of NMR

  报告了一种通过计算机辅助设计开发的在常压 CO2 下由碱官能化离子液体催化的二炔醇水合高效合成 3(2H)-呋喃酮的策略。首先预测了碱性离子液体作为催化剂的最佳范围，[HDBU][BenIm]表现出最高的催化活性。通过 NMR 光谱研究和量子化学计算的结合，结果表明阴离子碱性和离子液体中阳离子种类的重要性。
• In Situ Synthesis of CuN ₄ /Mesoporous N‐Doped Carbon for Selective Oxidative Crosscoupling of Terminal Alkynes under Mild Conditions
  作者：Yuanteng Zhang、Yong Wu、Yaqiong Su、Yue Cao、Zhenjin Liang、Dali Yang、Ruohan Yu、Dongchao Zhang、Jinsong Wu、Wei Xiao、Aiwen Lei、Dong Gu

  DOI：10.1002/smll.202105178

  日期：2022.3

  crosscoupling of terminal alkynes is an efficient chemical process for manufacturing asymmetrical 1,3-conjugated diynes. However, it often occurs in homogenous conditions and costs a lot for reaction treatment. Herein, a copper catalyzed strategy is used to synthesize highly ordered mesoporous nitrogen-doped carbon material (OMNC), and the copper species is in situ transformed into the copper single-atom

  1,3-共轭二炔是一类重要的化学中间体，末端炔烃的选择性交叉偶联是制备不对称1,3-共轭二炔的有效化学工艺。然而，它经常发生在均质条件下，反应处理成本很高。本文采用铜催化合成高度有序的介孔氮掺杂碳材料（OMNC），将铜物种原位转化为具有四氮配位的铜单原子位点（CuN 4）。这些特性使 CuN 4/OMNC 催化剂在温和条件 (40 °C) 和低底物比 (1.3) 下有效用于末端炔烃的选择性氧化交叉偶联，以及广泛的不对称和对称 1,3-二炔（26 个实例）。密度泛函理论 (DFT) 计算表明芳基-烷基交叉偶联在 CuN 4位点具有最低的能垒，这可以解释高选择性。此外，催化剂可以通过简单的离心或过滤分离和重复使用。这项工作可以为构建单原子负载的介孔材料以桥接均相和多相催化开辟一条简便的途径。
• Fiber-supported Pd Catalysts for Cross-coupling Reaction of Aromatic and Aliphatic Terminal Alkynes
  作者：Haijun Li、Xuejian Chen、Tingxian Tao、Xiaohan Lu、Renchun Yang、Rongmei Liu、Zhichuan Wu

  DOI：10.1007/s10562-019-02820-9

  日期：2019.9

  efficiency of cross-coupling reaction under mild condition and easy catalyst separation is a key issue in the realistically chemical industry application. Here, we report that the fiber-supported Pd catalyst shows a high activity and selectivity for the cross-coupling reaction of terminal alkynes. The yield of the asymmetric 1,3-diyne can reach 83% at 80 °C and 4 h reaction time in N,N-dimethylacetamide

  在温和条件下提高交叉偶联反应的效率和催化剂易于分离是实际化工应用中的关键问题。在这里，我们报告了纤维负载的 Pd 催化剂对末端炔烃的交叉偶联反应显示出高活性和选择性。在 N,N-二甲基乙酰胺 (DMAc) 中，在 80 °C 和 4 h 反应时间下，不对称 1,3-二炔的产率可达 83%，选择性约为 87%。XPS、EDS 和 SEM 结果表明 Pd 金属离子成功地负载到纤维表面，并在反应中被末端炔烃还原生成 Pd(0) 的活性组分。我们认为 Pd (0) 是催化循环的活性中心，纤维的配位可以稳定载体上的 Pd 颗粒并提高 Pd 催化剂的催化活性。Cu(I)起到协同催化作用。该研究为高效交叉偶联反应提供了一条替代途径。
• A simple method for the preparation of propargylamines using molecular sieve modified with copper(ii)
  作者：Anna Fodor、Árpád Kiss、Nóra Debreczeni、Zoltán Hell、Iván Gresits

  DOI：10.1039/c0ob00224k

  日期：——

  A new, heterogeneous, 4 Å molecular sieve-supported copper(II) catalyst was developed and was used successfully in the A3 coupling of alkynes, aldehydes and amines under simple reaction conditions.

  我们开发了一种新型、异质、4 Å 分子筛支撑的铜（II）催化剂，并在简单的反应条件下成功用于炔、醛和胺的 A3 偶联反应。
• Carbon dioxide-mediated synthesis of 3(2H)-furanones from diyne alcohols
  作者：Gaoqing Yuan、Zaijun He、Junhua Zheng、Zhengwang Chen、Huawen Huang、Dabin Shi、Chaorong Qi、Huanfeng Jiang

  DOI：10.1016/j.tetlet.2011.08.130

  日期：2011.11

  A novel type of carbon dioxide-mediated reaction of diyne alcohols without any metal catalysts was reported. Carbon dioxide held the key to the success of this reaction, in which 3(2H)-furanones were selectively obtained in moderate to high yields. (C) 2011 Elsevier Ltd. All rights reserved.