(Z)-1-methoxy-4-(4-phenylbut-3-en-1-ynyl)benzene | 1407152-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-1-methoxy-4-(4-phenylbut-3-en-1-ynyl)benzene
• 英文别名: 1-((Z)-4-(4-methoxyphenyl)but-1-en-3-ynyl)benzene；1-methoxy-4-[(3Z)-4-phenylbut-3-en-1-yn-1-yl]benzene；1-methoxy-4-(4-phenylbut-3-en-1-yn-1-yl)benzene；(Z)-1-phenyl-4-(4-methoxyphenyl)-but-1-en-3-yne；1-methoxy-4-[(Z)-4-phenylbut-3-en-1-ynyl]benzene
• CAS: 1407152-68-4
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: HTYPQCZNAOOYFD-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 silver nitrate 、 四丁基二氟三苯硅酸铵 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 16.0h， 生成 (Z)-1-methoxy-4-(4-phenylbut-3-en-1-ynyl)benzene
  参考文献：
  名称：

  铜催化乙烯基硅氧烷与溴炔的交叉偶联：烯炔的合成

  摘要：

  烯炔是有机合成中的多功能构建基块。呈现了铜催化的乙烯基硅氧烷与溴代炔烃的Hiyama型交叉偶联。这种温和而有效的方法导致形成各种敏感的烯炔。允许使用顺式，反式和1,1'-二取代的乙烯基硅氧烷，并且观察到立体化学的完全保留。诸如卤化物，不饱和酮和醛等敏感基团是完全可耐受的。

  DOI：

  10.1021/ol501140p

文献信息

• A polystyrene supported [PdCl–(SeCSe)] complex: a novel, reusable and robust heterogeneous catalyst for the Sonogashira synthesis of 1,2-disubstituted alkynes and 1,3-enynes
  作者：Elmira Mohammadi、Barahman Movassagh

  DOI：10.1039/c8nj01042k

  日期：——

  g−1). The PS[PdCl–SeCSe] catalytic activity has been evaluated in the Sonogashira coupling of diverse aryl halides with aromatic and aliphatic terminal alkynes. It was also noted that less reactive and inexpensive aryl bromides and aryl chlorides have been successfully cross-coupled with terminal alkynes using low catalyst loading. Moreover, the developed methodology is effective for the stereoselective

  3,5-双（（苯基硒基甲基）甲基）苯酚已通过多步合成从市售的5-羟基间苯二甲酸合成为新型SECSE夹钳型预配体。然后，使用包括FT-IR，SEM / EDX，TG / DTG和XPS在内的不同技术，制备并表征了聚苯乙烯负载的SECSE钳形配体及其相应的钯配合物。通过ICP分析确定的掺入聚合物基质中的钯的量为3.64wt％（0.34mmol g -1））。在各种芳基卤化物与芳族和脂族末端炔烃的Sonogashira偶联中，已评估了PS [PdCl–SECSE]的催化活性。还应注意的是，使用低催化剂负载量，已成功地将反应性较低且价格便宜的芳基溴化物和芳基氯化物与末端炔烃进行了交叉偶联。而且，开发的方法对于取代的1，3-烯炔的立体选择性制备是有效的。
• Copper-catalyzed deacetonative Sonogashira coupling
  作者：Yury N. Kotovshchikov、Artem A. Binyakovsky、Gennadij V. Latyshev、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1039/d2ob01267g

  日期：——

  assembling internal alkynes from tertiary propargyl alcohols and (het)aryl halides has been developed. The proposed tandem approach includes the base-promoted retro-Favorskii fragmentation followed by Cu-catalyzed C(sp)–C(sp2) cross-coupling. The use of inexpensive reagents (e.g. a catalyst, additives, a base, and a solvent) and good functional group tolerance make the procedure practical and cost-effective

  已经开发了一种方便的无钯和无膦方案，用于从叔炔丙醇和（杂）芳基卤化物组装内部炔烃。所提出的串联方法包括碱基促进的逆向 Favorskii 裂解，然后是铜催化的 C(sp)–C(sp 2 ) 交叉偶联。使用廉价的试剂（例如催化剂、添加剂、碱和溶剂）和良好的官能团耐受性使该程序实用且具有成本效益。该方法的合成效用通过源自天然甾体激素的乙烯基碘化物的平滑炔基化得到证实。
• Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes
  作者：Nicklas W. Buchbinder、Long H. Nguyen、Owen N. Beck、Andrew D. Bage、Carla Slebodnick、Webster L. Santos

  DOI：10.1021/acs.orglett.4c01929

  日期：2024.7.26

  alkyne-selective hydroboration of 1,3-enynes is disclosed, providing access to the previously elusive 2-boryl-1,3-dienes. Using CuOAc, Xantphos, and HBpin, Bpin was installed on the internal carbon of a series of symmetric and nonsymmetric 1,3-enynes, affording products with excellent Z:E selectivity. The utility of the 2-boryl-1,3-diene products was demonstrated by transformation to useful functional groups

  公开了铜催化的1,3-烯炔的炔烃选择性硼氢化反应，提供了获得先前难以捉摸的2-硼基-1,3-二烯的途径。使用CuOAc、Xantphos和HBpin，将Bpin安装在一系列对称和非对称1,3-烯炔的内部碳上，使产物具有优异的Z : E选择性。 2-硼基-1,3-二烯产品的实用性通过转化为有用的官能团得到证明。
• Highly regio- and stereoselective synthesis of 1,3-enynes from unactivated ethylenes via palladium-catalyzed cross-coupling
  作者：Yanmei Wen、Azhong Wang、Huanfeng Jiang、Shifa Zhu、Liangbin Huang

  DOI：10.1016/j.tetlet.2011.07.092

  日期：2011.11

  An efficient procedure for regio- and stereoselective synthesis of a series of conjugated enynes by a simple Pd-catalyzed cross-coupling reaction of unactivated ethylenes and ethynyl bromide has been developed. The reaction proceeds smoothly in DMF to give the corresponding products in good to excellent yields. The protocol can tolerate a broad range of functional groups on the substrates. (C) 2011 Elsevier Ltd. All rights reserved.
• Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes
  作者：Sabir Ahammed、Debasish Kundu、Brindaban C. Ranu

  DOI：10.1021/jo5011069

  日期：2014.8.15

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.