11,1'-(1,2-phenylene)bis(3-phenylprop-2-yne-1,1-diyl)dimethyl dicarbonate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 11,1'-(1,2-phenylene)bis(3-phenylprop-2-yne-1,1-diyl)dimethyl dicarbonate
• 英文别名: dibenzyl 1,2-phenylenebis(3-phenylprop-2-yne-1,1-diyl)dicarbonate；1,2-phenylenebis(3-phenylprop-2-yne-1,1-diyl) dimethyl dicarbonate；[1-[2-(1-Methoxycarbonyloxy-3-phenylprop-2-ynyl)phenyl]-3-phenylprop-2-ynyl] methyl carbonate；[1-[2-(1-methoxycarbonyloxy-3-phenylprop-2-ynyl)phenyl]-3-phenylprop-2-ynyl] methyl carbonate
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: UBEOVSARLHEBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  11,1'-(1,2-phenylene)bis(3-phenylprop-2-yne-1,1-diyl)dimethyl dicarbonate 在 四(三苯基膦)钯 、 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 5,12-二苯基并四苯
  参考文献：
  名称：

  PBr₃-Mediated Cyclization of 1,7-Diyn-3,6-bis(propargyl carbonate)s: Synthesis of 5-Bromotetracenes

  摘要：

  A new and straightforward method for the synthesis of 5-bromotetracenes through PBr3-mediated cyclization of 1,7-diyn-3,6-bis(propargyl carbonate)s has been developed. This method offers several advantages such as easily accessible starting materials, high efficiency, and wide functional group compatibility. In addition, chloro- and iodo-substituted tetracenes were also synthesized using appropriate halogenating reagents. The utility of the 5-bromotetracene products has been illustrated by their efficient transformations through various palladium-catalyzed cross-coupling reactions.

  DOI：

  10.1021/acs.joc.7b01519
• 作为产物：
  描述：

  邻苯二甲醛 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 11,1'-(1,2-phenylene)bis(3-phenylprop-2-yne-1,1-diyl)dimethyl dicarbonate
  参考文献：
  名称：

  钯催化的四烯和并五苯的高效合成。

  摘要：

  已开发了Pd（0）催化的1,7-二炔-3,6-双（炔丙基碳酸酯）与有机硼酸的级联反应，可一锅通达功能化的四烯或并五苯。

  DOI：

  10.1039/c2cc36700a

文献信息

• 并四苯及并五苯类化合物的合成方法
  申请人：中国科学院上海有机化学研究所

  公开号：CN103664499B

  公开（公告）日：2016-03-02

  本发明涉及并四苯及并五苯类化合物的合成方法。从简单易得的邻苯二甲醛类化合物和芳基乙炔出发，利用炔基锂试剂加成反应制备出多种双炔丙醇碳酸酯类化合物;在催化量钯试剂的存在下，双炔丙醇碳酸酯类化合物可以和有机硼酸通过串联反应，以良好到优秀的收率一步合成并四苯及并五苯类化合物。本方法具有原料易得、操作简单、条件温和、方便快捷、收率优秀等特点，利用本方法可以有效地在并四苯及并五苯的骨架上引入芳基和烷基。
• Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes
  作者：Ming Chen、Jun Liu、Lu Wang、Xiaobo Zhou、Yuanhong Liu

  DOI：10.1039/c3cc44757j

  日期：——

  Gold-catalyzed cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s leads to a highly efficient and diastereoselective synthesis of functionalized naphtho[b]cyclobutenes. A cascade sequence involving gold-catalyzed double 3,3-rearrangement, 6pi-electrocyclic reaction and a decarbonylative cyclization was proposed for this reaction.

  金催化的1,7-二炔-3,6-双（炔丙基碳酸酯）s的环异构化导致官能化萘[b]环丁烯的高效和非对映选择性合成。提出了涉及金催化的双3，3-重排，6-π-电环反应和脱羰环化的级联序列。
• Palladium-catalyzed highly efficient synthesis of tetracenes and pentacenes
  作者：Ming Chen、Yifeng Chen、Yuanhong Liu

  DOI：10.1039/c2cc36700a

  日期：——

  Pd(0)-catalyzed cascade reactions of 1,7-diyn-3,6-bis(propargyl carbonate) with organoboronic acids have been developed, which provide one-pot access to functionalized tetracenes or pentacenes.

  已开发了Pd（0）催化的1,7-二炔-3,6-双（炔丙基碳酸酯）与有机硼酸的级联反应，可一锅通达功能化的四烯或并五苯。
• PBr₃-Mediated Cyclization of 1,7-Diyn-3,6-bis(propargyl carbonate)s: Synthesis of 5-Bromotetracenes
  作者：Ning Sun、Haoyi Chen、Xiangdong Li、Murong Xu、Yi Gan、Liangwei Zhang、Yuanhong Liu

  DOI：10.1021/acs.joc.7b01519

  日期：2017.10.6

  A new and straightforward method for the synthesis of 5-bromotetracenes through PBr3-mediated cyclization of 1,7-diyn-3,6-bis(propargyl carbonate)s has been developed. This method offers several advantages such as easily accessible starting materials, high efficiency, and wide functional group compatibility. In addition, chloro- and iodo-substituted tetracenes were also synthesized using appropriate halogenating reagents. The utility of the 5-bromotetracene products has been illustrated by their efficient transformations through various palladium-catalyzed cross-coupling reactions.