diethyl 1-ethenylydene-1,3-dihydro-2H-indene-2,2-dicarboxylate | 950833-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: diethyl 1-ethenylydene-1,3-dihydro-2H-indene-2,2-dicarboxylate
• 英文别名: diethyl 1-vinylidene-1H-indene-2,2(3H)-dicarboxylate；diethyl 1-vinylidene-1H-indan-2,2(3H)-dicarboxylate
• CAS: 950833-51-9
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: HWPUTHAXQCCJLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  diethyl 1-ethenylydene-1,3-dihydro-2H-indene-2,2-dicarboxylate 、 4′-羟基-3′-碘苯乙酮 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以68%的产率得到diethyl 5-acetyl-3-methylidenespiro[1-benzofuran-2,3'-1H-indene]-2',2'-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：

  diethyl 2-(2-(3-hydroxyprop-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-ethenylydene-1,3-dihydro-2H-indene-2,2-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

文献信息

• Highly Regio- and Stereoselective Synthesis of Indene and Benzo[<i>b</i>]furan Derivatives via a Pd-Catalyzed Carboannulation of Propargyl Carbonates with Nucleophiles
  作者：Hai-Peng Bi、Li-Na Guo、Fa-Rong Gou、Xin-Hua Duan、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo8002776

  日期：2008.6.1

  A new and efficient synthesis of indene and benzo[b]furan derivatives has been achieved via Pd-catalyzed carboannulation of propargyl carbonates with nucleophiles in good to excellent yields with high regio- and stereoselectivity. A novel sequence of nucleophilic attack is observed, and a possible mechanism is proposed.

  通过钯催化碳酸炔丙基酯与亲核试剂的碳环化反应，实现了茚和苯并[ b ]呋喃衍生物的新型高效合成，具有良好的产率和良好的区域选择性和立体选择性。观察到一种新型的亲核攻击序列，并提出了可能的机制。
• New light on an old reaction: phase-transfer-catalyzed intramolecular cyclization of propargyl compounds for synthesis of indene derivatives and disubstituted benzo[b]furans
  作者：Peng-Shuai Sun、Jie Hu、Xiang-Chuan Wang、Lei Liu、Yong-Min Liang

  DOI：10.1016/j.tet.2011.12.055

  日期：2012.2

  A variety of indene derivatives and disubstituted benzo[b]furans are readily prepared under the mild reaction condition from propargylic compounds by phase-transfer catalysis (PTC) instead of metal catalysis.

  在温和的反应条件下，通过相转移催化（PTC）代替金属催化，由炔丙基化合物可轻松制得各种茚衍生物和二取代的苯并[ b ]呋喃。
• Highly Regioselective Synthesis of Spirocyclic Compounds by a Palladium-Catalyzed Intermolecular Tandem Reaction
  作者：Hai-Peng Bi、Xue-Yuan Liu、Fa-Rong Gou、Li-Na Guo、Xin-Hua Duan、Xing-Zhong Shu、Yong-Min Liang

  DOI：10.1002/anie.200702238

  日期：2007.9.17
• 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.
• New Insight into Ni(II)-Catalyzed Cyclization Reactions of Propargylic Compounds with Soft Nucleophiles: Novel Indenes Formation
  作者：Fa-Rong Gou、Hai-Peng Bi、Li-Na Guo、Zheng-Hui Guan、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo800155a

  日期：2008.5.1

  We have disclosed a very nice advance of nickel(II)-catalyzed carboannulation reactions. Highly substituted indene derivatives are readily prepared in moderate to excellent yields under very mild reaction conditions in air via a nickel (II)-catalyzed cyclization of propargylic compounds with soft nucleophiles.