Dimethyl 2,2-bis[3-(4-bromophenyl)prop-2-ynyl]propanedioate | 1311184-69-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: Dimethyl 2,2-bis[3-(4-bromophenyl)prop-2-ynyl]propanedioate
• 英文别名: dimethyl 2,2-bis[3-(4-bromophenyl)prop-2-ynyl]propanedioate
• CAS: 1311184-69-6
• 化学式: C₂₃H₁₈Br₂O₄
• 分子量: 518.202
• InChiKey: SYQLSHOCIHPXQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 2,2-bis[3-(4-bromophenyl)prop-2-ynyl]propanedioate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 甲醇 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 、 1,4-di-tert-butyl-1,4-diaza-1,3-butadiene 、 potassium tert-butylate 、 苄基三乙基氯化铵 、 甲酸:三乙胺 1:1 、 potassium carbonate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 31.0h， 生成
  参考文献：
  名称：

  Ruthenium-catalyzed cyclization/transfer hydrogenation of 1,6-diynes: unprecedented mode of alcohol activation via metallacyclopentatriene

  摘要：

  使用钌催化剂和 MeOH 作为 H2 替代​​物开发了 1,​​6-二炔的首次转移氢化环化，产生环外二烯。

  DOI：

  10.1039/c1cc13744a
• 作为产物：
  描述：

  二甲基-2.2-二(丙-2-炔基)丙二酸二乙酯 、 对溴碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 反应 5.0h， 以92%的产率得到Dimethyl 2,2-bis[3-(4-bromophenyl)prop-2-ynyl]propanedioate
  参考文献：
  名称：

  Ruthenium-catalyzed cyclization/transfer hydrogenation of 1,6-diynes: unprecedented mode of alcohol activation via metallacyclopentatriene

  摘要：

  使用钌催化剂和 MeOH 作为 H2 替代​​物开发了 1,​​6-二炔的首次转移氢化环化，产生环外二烯。

  DOI：

  10.1039/c1cc13744a

文献信息

• Practical Solvent-Free Ruthenium Trichloride-Mediated Benzannulation Approach to Fused Functionalized Arenes
  作者：Jeremy Jacquet、Anne-Laure Auvinet、Anil Kumar Mandadapu、Mansour Haddad、Virginie Ratovelomanana-Vidal、Véronique Michelet

  DOI：10.1002/adsc.201500186

  日期：2015.5.4

  The solvent‐ and ligand‐free [2+2+2] ruthenium‐promoted cycloaddition of α,ω‐diynes and alkynes provides a facile and efficient strategy for the synthesis of substituted benzene‐derived systems. The search for the optimal reaction conditions revealed the unprecedented catalytic activity of ruthenium trichloride for benzannulation reactions and this atom‐economical process allowed the synthesis of fused

  无溶剂和无配体的[2 + 2 + 2]钌促进的α，ω-二炔和炔烃的环加成反应为合成取代苯衍生的体系提供了便捷而有效的策略。对最佳反应条件的探索揭示了三氯化钌对苯环化反应具有空前的催化活性，并且这种原子经济的过程允许以高产率高收率地合成包括二氢苯并呋喃，异吲哚啉，茚满的稠合芳烃。该实用方案还引发了五取代芳族衍生物的制备，并被用于功能化杂环的1克级合成。
• Synthesis of Siloles via Rhodium-Catalyzed Cyclization of Alkynes and Diynes with Hexamethyldisilane
  作者：Takanori Matsuda、Yuya Suda、Yosuke Fujisaki

  DOI：10.1055/s-0030-1259914

  日期：2011.4

  A rhodium-catalyzed silylative cyclization of alkynes and 1,6-diynes with hexamethyldisilane is described. These reactions enable the synthesis of densely substituted silole derivatives through the use of a rhodium(I)-norborna-2,5-diene complex as a catalyst.

  描述了炔烃和 1,6-二炔与六甲基乙硅烷的铑催化甲硅烷基化环化。这些反应能够通过使用铑 (I)-norborna-2,5-二烯配合物作为催化剂来合成密集取代的硅酮衍生物。
• Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents
  作者：Takanori Matsuda、Kentaro Suzuki

  DOI：10.1002/ejoc.201500252

  日期：2015.5

  anhydrides function as synthetic equivalents of alkynes in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve a formal [2+2+2] cyclotrimerization. This approach is useful for reactions involving alkynes with low boiling points or severe ring strain. Hard-to-access [2+2+2] cycloadducts are available through this new cycloaddition strategy by employing easy-to-handle alkyne equivalents.

  取代的马来酸酐在铑 (III) 催化与 1,6-二炔的反应中用作炔烃的合成等价物，以实现正式的 [2+2+2] 环三聚反应。这种方法对于涉及低沸点或严重环应变的炔烃的反应很有用。通过采用易于处理的炔烃等价物，通过这种新的环加成策略可以获得难以获得的 [2+2+2] 环加合物。
• Ruthenium-Catalyzed Transfer Oxygenative Cyclization of α,ω-Diynes: Unprecedented [2 + 2 + 1] Route to Bicyclic Furans via Ruthenacyclopentatriene
  作者：Ken Yamashita、Yoshihiko Yamamoto、Hisao Nishiyama

  DOI：10.1021/ja302868s

  日期：2012.5.9

  A novel oxygen-atom-transfer process enables the catalytic [2 + 2 + 1] synthesis of bicyclic furans from alpha,omega-diynes with DMSO. [CpRu(AN)(3)]PF6 catalyzed the transfer oxygenative cyclization of diynes with aryl terminal groups, while those of diynes with alkyl terminal groups were effectively promoted by the corresponding Cp* complex. A mechanism for bicyclic furan formation via a ruthenacyclopentatriene was proposed on the basis of both experimental and theoretical studies.
• Ruthenium-Catalyzed Transfer-Hydrogenative Cyclization of 1,6-Diynes with Hantzsch 1,4-Dihydropyridine as a H₂Surrogate
  作者：Yoshihiko Yamamoto、Shota Mori、Masatoshi Shibuya

  DOI：10.1002/chem.201301846

  日期：2013.9.2

  AbstractThe transfer‐hydrogenative cyclization of 1,6‐diynes with Hantzsch 1,4‐dihydropyridine as a H2 surrogate was performed in the presence of a cationic ruthenium catalyst of the type [Cp′Ru(MeCN)3PF6]. Exocyclic 1,3‐dienes or their 1,4‐hydrogenation products, cycloalkenes, were selectively obtained, depending on the substrate structure and the reaction conditions.