dimethyl 3-formyl-4-methylcyclopent-3-ene-1,1-dicarboxylate | 63104-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 3-formyl-4-methylcyclopent-3-ene-1,1-dicarboxylate
• 英文别名: Dimethyl 3-formyl-4-methylcyclopent-3-ene-1,1-dicarboxylate
• CAS: 63104-51-8
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: ARWOJWMIWIBCEU-UHFFFAOYSA-N

物化性质

• 沸点：
  289.8±40.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl (E)-3-(acetoxymethylene)-4-methylenecyclopentane-1,1-dicarboxylate 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 溶剂黄146 作用下， 反应 1.0h， 以80%的产率得到dimethyl 3-formyl-4-methylcyclopent-3-ene-1,1-dicarboxylate
  参考文献：
  名称：

  钌催化的1,6-二炔的脱羰环化反应。

  摘要：

  Ruthenium-catalyxed tandem cyclization-decarbonylation of terminal 1,6-diynes give exo -alkykidenecyclopentanes. The starting point of this process is likely to be the formation of an Ru-vinylidene complex.

  DOI：

  10.1021/ja0752888

文献信息

• Cobalt-Catalyzed Cyclization/Hydroboration of 1,6-Diynes with Pinacolborane
  作者：Qiang Huang、Meng-Yang Hu、Shou-Fei Zhu

  DOI：10.1021/acs.orglett.9b02873

  日期：2019.10.4

  Herein, we report a protocol for cyclization/hydroboration of 1,6-diynes with pinacolborane using a cobalt catalyst generated in situ from a Co(II)-phenanthroline complex, tetrabutylammonium fluoride, and pinacolborane. This protocol, which features good functional group tolerance, a broad substrate scope, and excellent stereoselectivity, enables the synthesis of useful cyclic 1,3-dienylboron compounds

  在本文中，我们报告了一种使用频哪醇硼烷使用从Co（II）-菲咯啉配合物，氟化四丁基铵和频萘酚硼烷原位生成的钴催化剂进行1,6-二炔与环己硼烷的环化/加氢硼化的方案。该方案具有良好的官能团耐受性，广泛的底物范围和出色的立体选择性，可从易于获得的原料合成有用的环状1,3-二烯基硼化合物。如对照实验所示，所提出的机理涉及低价钴促进的环金属化和随后的硼氢化。我们的发现表明，将硼氢化与CC键形成相结合是合成结构多样的有机硼烷的有效方法。
• Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes
  作者：Qian Zhang、Qiu-Ju Liang、Jian-Lin Xu、Yun-He Xu、Teck-Peng Loh

  DOI：10.1039/c8cc00097b

  日期：——

  An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products

  开发了1，6-二炔的加成/环化反应，用于合成高度取代的1，2-二亚烷基环烷烃。在这项工作中，1,6-二炔与（二甲基苯基甲硅烷基）频哪醇-硼烷在钯催化剂的存在下反应，以良好的收率获得了具有（Z，Z）-构型的甲硅烷基和硼烷基的1,2-二亚烷基环烷烃。而且，相应的产物可以容易地转化成其他合成上有用的化合物。该协议为不饱和1，6-二炔的杂元素-元素键连接提供了一种有效且实用的方法。
• Metal-Catalyzed Carbocyclization by Intramolecular Reaction of Allylsilanes and Allylstannanes with Alkynes
  作者：Carolina Fernández-Rivas、María Méndez、Antonio M. Echavarren

  DOI：10.1021/ja993524b

  日期：2000.2.1
• Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones
  作者：Carlos González-Rodríguez、Luz Escalante、Jesús A. Varela、Luis Castedo、Carlos Saá

  DOI：10.1021/ol900142r

  日期：2009.4.2

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.
• Direct Carbocyclization of Aldehydes with Alkynes:  Combining Gold Catalysis with Aminocatalysis
  作者：Jörg T. Binder、Benedikt Crone、Timm T. Haug、Helge Menz、Stefan F. Kirsch

  DOI：10.1021/ol800092p

  日期：2008.3.1

  A combination of gold(l) complexes and amine bases catalyzes the 5-exo-dig cyclization of formyl alkynes. This direct alpha-functionalization of aldehydes with unactivated alkynes does not involve the use of preformed enol equivalents.