1-Carbomethoxy-3,3-dimethyl-1-phenylallene | 92421-07-3

• 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: 1-Carbomethoxy-3,3-dimethyl-1-phenylallene
• 英文别名: methyl 4-methyl-2-phenyl-penta-2,3-dienoate；methyl 4-methyl-2-phenylpenta-2,3-dienoate-2-phenylpenta-2,3-dienoate
• CAS: 92421-07-3
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YDRWVAFIHJGNSB-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 0.5 Torr)
• 密度：
  1.002±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基氯化镁 、 1-Carbomethoxy-3,3-dimethyl-1-phenylallene 在 copper(l) chloride 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到methyl 3,4-dimethyl-2-phenyl-3-pentenoate
  参考文献：
  名称：

  CuCl催化的格氏试剂与2,3-烯丙酸酯的立体选择性共轭加成

  摘要：

  发现CuCl是2,3-脲基酸酯与Grignard试剂共轭加成以高立体选择性，高产率到优良产率合成多取代的β，γ-不饱和链烯酸酯的有效催化剂。伯，仲和叔烷基，乙烯基或苯基格氏试剂均可使用。

  DOI：

  10.1016/j.tet.2012.01.027
• 作为产物：
  描述：

  2-甲基-3-丁炔-2-醇 在 palladium diacetate 、 四(三苯基膦)钯 copper(l) iodide 、 sodium hydride 、 二乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 65.0h， 生成 1-Carbomethoxy-3,3-dimethyl-1-phenylallene
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086

文献信息

• A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
  作者：Guobi Chai、Shangze Wu、Chunling Fu、Shengming Ma

  DOI：10.1021/ja1108694

  日期：2011.3.23

  polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically

  描述了一种合成多取代环丁烯酮的有效方法，由于固有的环应变，这些方法不易从传统方法中获得。2,3-烯丙酸酯和有机锌试剂的反应通过串联迈克尔加成/环状 1,2-加成/消除机制进行，来自有机锌试剂的官能团被区域特异性地引入环丁烯酮产物的 3-位优良的产量。演示了在立体定义的 β,γ-不饱和烯酮的合成中的应用。
• Benzo[<i>e</i>]isoindole-1,3-diones as Potential Inhibitors of Glycogen Synthase Kinase-3 (GSK-3). Synthesis, Kinase Inhibitory Activity, Zebrafish Phenotype, and Modeling of Binding Mode
  作者：Haixia Zou、Liyan Zhou、Yuanzhen Li、Yi Cui、Hanbing Zhong、Zhengying Pan、Zhen Yang、Junmin Quan

  DOI：10.1021/jm9013373

  日期：2010.2.11

  Benzo[e]isoindole-1,3-dione derivatives were synthesized, and the effects on GSK-3 beta activity and zebrafish embryo growth were evaluated. A series of derivatives show obvious inhibitory activity against GSK-3 beta. The most potent inhibitor, 7,8-dimethoxy-5-methylbenzo[e]isoindole-1,3-dione (8a), shows nanomolar IC50 and obvious phenotype on zebrafish embryo growth associated with the inhibition of GSK-3 beta at low micromolar concentration. The interaction mode between 8a and GSK-3 beta was characterized by computational modeling.
• Cyclopropane photochemistry. 27. Cycloaddition reactions of strained ring systems. Photochemistry of 1-phenyl-2-carbomethoxy-3,3-dimethylcyclopropene
  作者：Albert Padwa、G. Davon Kennedy

  DOI：10.1021/jo00197a004

  日期：1984.11
• Diversified assembly of perfluoroalkyl-substituted furans and 2,5-dihydrofuran-2-ols
  作者：Guofei Chen、Guangke He、Can Xue、Chunling Fu、Shengming Ma

  DOI：10.1016/j.tetlet.2010.10.085

  日期：2011.1

  We have developed a facile and effective synthesis of 3-iodofurans from 3-monosubstituted 1,2-allenyl perfluoroalkyl ketones or 2-hydroxy-4-iodo-2,5-dihydrofurans from 3,3-disubstituted 1,2-allenyl perfluoroalkyl ketones. The perfluoroalkyl substituent and the amount of water in the solvent are important for the success of this electrophilic cyclization. (C) 2010 Elsevier Ltd. All rights reserved.
• PADWA, A.;KENNEDY, G. D., J. ORG. CHEM., 1984, 49, N 23, 4344-4352
  作者：PADWA, A.、KENNEDY, G. D.

  DOI：——

  日期：——