diethyl 2-(2-(3-hydroxy-3-(p-tolyl)prop-1-ynyl)benzyl)malonate | 927685-21-0

• 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: diethyl 2-(2-(3-hydroxy-3-(p-tolyl)prop-1-ynyl)benzyl)malonate
• 英文别名: diethyl 2-(2-(3-hydroxy-3-p-tolylprop-1-ynyl)benzyl)malonate；Diethyl 2-[[2-[3-hydroxy-3-(4-methylphenyl)prop-1-ynyl]phenyl]methyl]propanedioate；diethyl 2-[[2-[3-hydroxy-3-(4-methylphenyl)prop-1-ynyl]phenyl]methyl]propanedioate
• CAS: 927685-21-0
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: RCKRRPJWRMPHCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-(3-hydroxy-3-(p-tolyl)prop-1-ynyl)benzyl)malonate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 diethyl 1-(2-p-tolylvinylidene)-1H-indene-2,2(3H)-dicarboxylate
  参考文献：
  名称：

  Highly Regioselective Synthesis of Indene Derivatives Including an Allene Functional Group via Pd/C-Catalyzed Cyclization Reaction in Air

  摘要：

  Indene derivatives including an allene functional group are readily prepared in moderate to excellent yields with high regioselectivity under very mild reaction conditions by the Pd/C-catalyzed reaction of propargylic compounds. The resulting products can be further elaborated using Pd-catalyzed annulation reactions.

  DOI：

  10.1021/ol071385u
• 作为产物：
  描述：

  丙二酸二乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 反应 14.0h， 生成 diethyl 2-(2-(3-hydroxy-3-(p-tolyl)prop-1-ynyl)benzyl)malonate
  参考文献：
  名称：

  通过亲电环化对茚衍生物进行高度区域和立体选择性合成。

  摘要：

  [反应：见正文]通过炔属丙二酸酯和酮与I2，IC1或NIS的反应，在非常温和的反应条件下，可以以中等至优异的收率和高的区域选择性和立体选择性轻松制备茚或萘衍生物。所得的碘化物可使用钯催化的偶联反应进一步精制。

  DOI：

  10.1021/ol062683e

文献信息

• Highly Regioselective Synthesis of Benz[<i>a</i>]anthracene Derivatives via a Pd-Catalyzed Tandem C−H Activation/Biscyclization Reaction
  作者：Zhi-Hui Ren、Zheng-Hui Guan、Yong-Min Liang

  DOI：10.1021/jo802712n

  日期：2009.4.17

  A palladium-catalyzed tandem C−H activation/biscyclization reaction of propargylic carbonates with terminal alkynes was determined, which allowed the tetracyclic benz[a]anthracene framework to be constructed with high regioselectivity. A possible mechanism for this tandem C−H activation/biscyclization process was discussed.

  确定了钯催化碳酸炔丙基酯与末端炔烃的串联CH活化/双环化反应，从而可以高区域选择性构建四环苯并[ a ]蒽骨架。讨论了此串联CH活化/双环化过程的可能机制。
• Highly Regio- and Stereoselective Synthesis of Indene Derivatives via Electrophilic Cyclization
  作者：Hai-Peng Bi、Li-Na Guo、Xin-Hua Duan、Fa-Rong Gou、Shu-Hao Huang、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol062683e

  日期：2007.2.1

  [reaction: see text] Indene or naphthalene derivatives are readily prepared in moderate to excellent yields with high regio- and stereoselectivity under very mild reaction conditions by the reaction of acetylenic malonates and ketones with I2, ICl, or NIS. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.

  [反应：见正文]通过炔属丙二酸酯和酮与I2，IC1或NIS的反应，在非常温和的反应条件下，可以以中等至优异的收率和高的区域选择性和立体选择性轻松制备茚或萘衍生物。所得的碘化物可使用钯催化的偶联反应进一步精制。
• Highly Regioselective Synthesis of Indene Derivatives Including an Allene Functional Group via Pd/C-Catalyzed Cyclization Reaction in Air
  作者：Hai-Peng Bi、Xue-Yuan Liu、Fa-Rong Gou、Li-Na Guo、Xin-Hua Duan、Yong-Min Liang

  DOI：10.1021/ol071385u

  日期：2007.8.1

  Indene derivatives including an allene functional group are readily prepared in moderate to excellent yields with high regioselectivity under very mild reaction conditions by the Pd/C-catalyzed reaction of propargylic compounds. The resulting products can be further elaborated using Pd-catalyzed annulation reactions.