dimethyl (2-ethynylbenzyl)malonate | 1236168-24-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (2-ethynylbenzyl)malonate
• 英文别名: 2-(2-ethynylbenzyl)malonic acid dimethyl ester；dimethyl 2-(2-ethynylbenzyl)malonate；dimethyl 2-[(2-ethynylphenyl)methyl]propanedioate
• CAS: 1236168-24-3
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: PGKAQFNHJVNIEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-ethynylbenzyl)malonate 在 copper(l) iodide 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到1-methyleneindan-2,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  通过顺序多催化级联反应快速合成功能化茚、三唑和糖皮质激素受体调节剂

  摘要：

  通过2-乙炔基苯甲醛、CH酸、有机氢化物和叠氮化物在催化量的L存在下的多催化级联反应，首次实现了合成取代茚和1,2,3-三唑的通用方法-脯氨酸/CuI/DIPEA。在本次交流中，我们发现了一种铜催化剂可用于两种不同的反应，并展示了其在糖皮质激素受体调节剂的高产合成中的合成应用。

  DOI：

  10.1002/ejoc.201000220
• 作为产物：
  描述：

  5-[(2-Ethynylphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione 在 重氮甲烷 作用下， 以 甲醚 为溶剂， 反应 2.0h， 生成 dimethyl (2-ethynylbenzyl)malonate
  参考文献：
  名称：

  Rapid two-step synthesis of drug-like polycyclic substances by sequential multi-catalysis cascade reactions

  摘要：

  通过将级联的TCRA/C-烯丙基化/烯炔-环化/狄尔斯-阿尔德反应作为关键步骤，从简单的非环状底物出发，成功实现了一种高效的氨基酸/自催化/碱性/钌/热催化的两步合成功能化药物类碳环的过程。在本次交流中，我们报告了通过将有机催化与钌催化结合进行药物类碳环的两步合成。

  DOI：

  10.1039/b920152a

文献信息

• Copper(I)-Catalysed Domino Coupling and Cyclisation Reaction: A Mild, Expedient Route for the Synthesis of Indene and Dihydronaphthalene Derivatives
  作者：Gullapalli Kumaraswamy、Guniganti Balakishan

  DOI：10.1002/ejoc.201500284

  日期：2015.5

  A substoichiometric copper iodide catalysed synthesis of indene and dihydronaphthalene derivatives has been accomplished. This protocol is compatible with functional groups, and results in various scaffolds of indene and dihydronaphthalene derivatives in good to high yields. By employing this protocol, a functionalised cyclohexenone derivative is also achieved.

  已经完成了亚化学计量的碘化铜催化合成茚和二氢萘衍生物。该协议与官能团兼容，并导致茚和二氢萘衍生物的各种支架以良好到高产率。通过使用该协议，还实现了功能化的环己烯酮衍生物。
• One pot synthesis of indene through copper(i)-catalyzed three-components coupling and cyclization reaction
  作者：Xiang-Chuan Wang、Mei-Jin Zhong、Yong-Min Liang

  DOI：10.1039/c2ob07071e

  日期：——

  A new and efficient synthesis of substituted indene has been achieved via copper(I)-catalyzed domino three-component coupling and cyclization reaction in moderate to good yield.

  一种新型高效的取代基合成 茚已经实现经由铜（我在中度至良好的产率）催化多米诺三组分偶联和环化反应。
• Hypervalent iodine-mediated regioselective cyclization of acetylenic malonates: facile synthesis of 1-diiodomethylene indane and cyclopentane derivatives
  作者：Chen Zheng、Renhua Fan

  DOI：10.1039/c1cc15529f

  日期：——

  A facile synthesis of potentially useful 1-diiodomethylene indanes and cyclopentanes from the regioselective cyclization of acetylenic malonates with the combination of iodosobenzene with tetrabutylammonium iodide in 2,2,2-trifluoroethanol is reported.

  据报道，在 2,2,2-三氟乙醇中，用碘代苯与四丁基碘化铵组合，通过炔属丙二酸酯的区域选择性环化，轻松合成了潜在有用的 1-二碘亚甲基茚满和环戊烷。
• Cascade Reactions: A Multicomponent Approach to Functionalized Indane Derivatives by a Tandem Palladium- Catalyzed Carbamoylation/Carbocylization Process
  作者：Bartolo Gabriele、Lucia Veltri、Raffaella Mancuso、Carla Carfagna

  DOI：10.1002/adsc.201301051

  日期：2014.8.11

  AbstractA novel, multicomponent and stereoselective approach to functionalized indane derivatives is reported. It is based on a tandem process consisting of Pd‐catalyzed oxidative carbamoylation of 2‐(2‐ethynylbenzyl)malonates with carbon monoxide, a secondary amine, and oxygen (with formation of a propiolamide intermediate), followed by carbocyclization, occurring through intramolecular addition of an in situ formed carbanion to the propiolamide moiety.magnified image
• Rapid two-step synthesis of drug-like polycyclic substances by sequential multi-catalysis cascade reactions
  作者：Dhevalapally B. Ramachary、Rumpa Mondal、Chintalapudi Venkaiah

  DOI：10.1039/b920152a

  日期：——

  An efficient amino acid-/self-/base-/ruthenium-/thermal-catalyzed two-step process for the synthesis of functionalized drug-like carbocycles was achieved through combinations of cascade TCRA/C-allylation/enyne-RCM/Diels–Alder reactions as key steps starting from simple acyclic substrates. In this communication, we report the two-step synthesis of drug-like carbocycles through a combination of organocatalysis with ruthenium-catalysis.

  通过将级联的TCRA/C-烯丙基化/烯炔-环化/狄尔斯-阿尔德反应作为关键步骤，从简单的非环状底物出发，成功实现了一种高效的氨基酸/自催化/碱性/钌/热催化的两步合成功能化药物类碳环的过程。在本次交流中，我们报告了通过将有机催化与钌催化结合进行药物类碳环的两步合成。