5-(2-(benzo[o][1,3]dioxol-5-yl)ethynyl)benzo[o][1,3]dioxole | 79238-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(2-(benzo[o][1,3]dioxol-5-yl)ethynyl)benzo[o][1,3]dioxole
• 英文别名: dipiperonylacetylene；5,5'-(Ethyne-1,2-diyl)bis(2H-1,3-benzodioxole)；5-[2-(1,3-benzodioxol-5-yl)ethynyl]-1,3-benzodioxole
• CAS: 79238-83-8
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: KQXKNNCQXQZYCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-(benzo[o][1,3]dioxol-5-yl)ethynyl)benzo[o][1,3]dioxole 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 5-[(E)-2-(1,3-benzodioxol-5-yl)-1,2-dibromoethenyl]-1,3-benzodioxole
  参考文献：
  名称：

  An unusual one step synthesis of acetylenes

  摘要：

  DOI：

  10.1016/s0040-4039(01)92916-8
• 作为产物：
  描述：

  5-((E)-2-nitroethenyl)-1,3-benzodioxole 在 双氧水 、 三乙胺 作用下， 以29%的产率得到5-(2-(benzo[o][1,3]dioxol-5-yl)ethynyl)benzo[o][1,3]dioxole
  参考文献：
  名称：

  An unusual one step synthesis of acetylenes

  摘要：

  DOI：

  10.1016/s0040-4039(01)92916-8

文献信息

• The use of calcium carbide in one-pot synthesis of symmetric diaryl ethynes
  作者：Weiwei Zhang、Huayue Wu、Zhiqing Liu、Ping Zhong、Lin Zhang、Xiaobo Huang、Jiang Cheng

  DOI：10.1039/b607809e

  日期：——

  An efficient Pd-catalyzed copper and amine free coupling reaction of acetylene and aryl bromides was achieved with calcium carbide as an acetylene source, using inorganic base and easily prepared, air-stable aminophosphine ligand in common organic solvents, providing symmetric diaryl ethynes in one-pot with yields ranged from moderate to excellent.

  实现了一种高效的无铜无胺催化乙炔与溴苯的偶联反应，以碳化钙为乙炔源，采用常见有机溶剂中的无机碱和易于制备、对空气稳定氨基膦配体，一步法合成对称二芳基乙炔，产率从中等到优异不等。
• Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid
  作者：Chao Fan、Jing Hou、Yu-Jia Chen、Kui-Ling Ding、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.1c00234

  日期：2021.3.19

  A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

  开发了铑用甲酸催化炔烃的加氢甲酰化反应。该方法无需处理有毒的CO气体就可以高产率和E选择性地提供α，β-不饱和醛。
• Fusing Carborane Carboxylic Acids with Alkynes: 3D Analogues of Isocoumarins via Regioselective B−H Activation
  作者：Furong Lin、Yunjun Shen、Yuanbin Zhang、Yuji Sun、Jiyong Liu、Simon Duttwyler

  DOI：10.1002/chem.201703802

  日期：2018.1.12

  between monocarba‐closo‐dodecaborate carboxylic acids and diarylacetylenes is reported. Regioselective activation of the B2 position, followed by B−C bond formation and ring closure, affords 3D bora‐analogues of isocoumarins. The reaction tolerates a variety of functional groups on the aromatic rings and can be extended to B12‐substituted derivatives. Furthermore, subsequent alkenylation of the B4 vertex

  之间monocarba-铱催化的烯基/环序列闭合碳报道-dodecaborate羧酸和diarylacetylenes。B2位置的区域选择性激活，接着是B-C键形成和环闭合，提供了异香豆素的3D硼烷类似物。该反应可耐受芳环上的各种官能团，并可扩展至B12取代的衍生物。此外，已经以高收率实现了B4顶点的后续烯基化。
• A Novel Fluorescent Skeleton from Disubstituted Thiochromenones via Nickel-Catalyzed Cycloaddition of Sulfobenzoic Anhydrides with Alkynes
  作者：Pengbing Mi、Lirong He、Tanxiao Shen、Jing Zhi Sun、Hui Zhao

  DOI：10.1021/acs.orglett.9b02161

  日期：2019.8.16

  Nickel-catalyzed cycloaddition of alkynes and 2-sulfobenzoic anhydrides gives highly functionalized thiochromenones. The reaction undergoes a deoxygenative rather than decarbonylative pathway and shows advantages of an excellent isolated yield (up to 95%), high reaction efficiency, and high regioselectivity. As one of the resulted products, 2,3-di(triphenylamine)-thiolchromenone possesses a typical

  炔烃和2-磺基苯甲酸酐的镍催化环加成反应可得到高度官能化的硫代色酮。该反应经历了脱氧而不是脱羰的途径，并显示出优异的分离产率（高达95％），高反应效率和高区域选择性的优点。作为所得产物之一，2，3-二（三苯胺）-硫羟色酮具有典型的聚集诱导的发射性质并发射有效的近红外荧光。
• Palladium(<scp>ii</scp>)-catalyzed synthesis of indenones through the cyclization of benzenecarbaldehydes with internal alkynes
  作者：Jajula Kashanna、Rathod Aravind Kumar、Ravada Kishore

  DOI：10.1039/c9ra03921j

  日期：——

  The palladium(II)-catalyzed carbocyclization of benzenecarbaldehydes with internal alkynes to afford 2,3-disubstituted indenones was reported. The annulation reaction proceeded through the transmetalation of Pd(II) with an aromatic aldehyde and the insertion of internal alkynes, followed by cyclization via the intramolecular nucleophilic addition of intermediate organopalladium(II) species to the aldehyde

  报道了钯( II )催化的苯甲醛与内部炔烃的碳环化反应得到2,3-二取代茚酮。环化反应通过 Pd( II ) 与芳香醛的金属转移和内部炔烃的插入进行，然后通过中间有机钯( II ) 物质与醛基的分子内亲核加成环化。该反应以中等至良好的产率进行，具有高区域选择性。