2-styryl-1,3-dioxolane

• 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-styryl-1,3-dioxolane
• 英文别名: 1,3-Dioxolane, 2-(2-phenylethenyl), (Z)；2-[(Z)-2-phenylethenyl]-1,3-dioxolane
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: JQLASNFFJHGQTK-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-phenyl-6,7-dihydro-5H-1,4-dithiepin-2-yl)-1,3-dioxolane 在 镍 氢气 作用下， 以 丙酮 为溶剂， 生成 2-styryl-1,3-dioxolane
  参考文献：
  名称：

  Photooxidation of Methyldithiepins into Dithiepin Carboxaldehydes in Carbon Tetrachloride

  摘要：

  [GRAPHICS]Methyldihydrodithiepins are converted into the corresponding carboxaldehydes via a simple and efficient oxidation by oxygen in carbon tetrachloride. The reaction is not a radical chain process, The proposed mechanism involves photoinduced electron transfer from the starting dithiepin to solvent (CCl4) followed by a series of events depicted in Scheme 1, The critical feature of the mechanism is that formation of superoxide (O-2(.-)) is avoided, preventing direct oxidation of sulfur atoms.

  DOI：

  10.1021/ol990870p

文献信息

• NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers
  作者：Zi-juan Wan、Jin-yuan Wang、Jun Luo

  DOI：10.1016/j.tetlet.2019.01.039

  日期：2019.2

  A direct alkenylation of cyclic ethers via radical cross decarboxylative coupling process catalyzed by NiCl2 and using DTBP as radical initiator and oxidant was developed. A variety of arylpropiolic acids and cyclic ethers were transformed into the corresponding 2-arylvinyl cyclic ethers in moderate to excellent yields. Mechanistic experiments were conducted to determine the nature of the reaction

  通过NiCl 2催化并以DTBP为自由基引发剂和氧化剂，通过自由基交叉脱羧偶联过程对环醚进行直接烯基化反应。将各种芳基丙酸和环状醚以中等至优异的产率转化为相应的2-芳基乙烯基环状醚。进行了机理实验以确定反应中间体的性质，并提出了一种可行的反应机理，该机理涉及NiCl 2促进的自由基过程。
• Copper-Catalyzed Hydroalkylation of Alkynes: Addition of sp³ C-H Bonds Across Carbon-Carbon Triple Bonds
  作者：Yuhong Zhang、Lehao Huang、Kai Cheng、Bangben Yao、Jinlong Zhao

  DOI：10.1055/s-0029-1216991

  日期：2009.10

  The regioselective copper-catalyzed addition of sp³ C-H bonds adjacent to an oxygen atom to various alkynes has been accomplished under mild reactions conditions in the presence of tert-butyl hydroperoxide to give the corresponding alkenylated products. C-H activation - copper - addition reactions - alkynes - tert-butyl hydroperoxide

  在温和的反应条件下，在叔丁基氢过氧化物的存在下，在氧原子附近的区域选择性铜催化的sp³CH键与铜的加成反应，得到相应的烯基化产物。 CH活化-铜-加成反应-炔烃-叔丁基过氧化氢
• Peroxide-Free Co(OAc)2-Catalyzed Radical Addition of sp3 C–H Bonds to Alkynes
  作者：Wanzhi Chen、Min Zhang、Yun Zhao

  DOI：10.1055/s-0036-1588909

  日期：——

  Abstract Cobalt-catalyzed radical addition of C–H bonds adjacent to an oxygen atom towards alkynes is described. The reaction proceeded at 60 °C without using additional radical initiators, and leads to 2-vinyl ether derivatives in good yields. Cobalt-catalyzed radical addition of C–H bonds adjacent to an oxygen atom towards alkynes is described. The reaction proceeded at 60 °C without using additional

  摘要 描述了在氧原子附近向炔烃的钴催化的C–H键的自由基加成反应。反应在60℃下进行，无需使用额外的自由基引发剂，并以良好的收率得到2-乙烯基醚衍生物。 描述了在氧原子附近向炔烃的钴催化的C–H键的自由基加成反应。反应在60℃下进行，无需使用额外的自由基引发剂，并以良好的收率得到2-乙烯基醚衍生物。
• The rapid photomediated alkenylation of 2-alkyl-1,3-dioxolanes with alkynes: a stereoelectronically assisted chain reaction
  作者：Niall W. A. Geraghty、Andrea Lally

  DOI：10.1039/b608979h

  日期：——

  The photomediated reaction of alkynes such as DMAD with 1,3-dioxolanes leads to remarkably rapid alkenylation; evidence is presented that these reactions occur via a chain mechanism.

  如DMAD等炔烃与1,3-二氧杂环烷的光介导反应导致了显著快速的烯基化；有证据表明这些反应是通过链式机制进行的。
• Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes
  作者：Nicolas Daubresse、Charlette Francesch、Christian Rolando

  DOI：10.1016/s0040-4020(98)00631-0

  日期：1998.9

  Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials. (C) 1998 Elsevier Science Ltd. All rights reserved.