ethyl 3-(2-(3,3-dimethylbut-1-ynyl)phenyl)-3-oxopropanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(2-(3,3-dimethylbut-1-ynyl)phenyl)-3-oxopropanoate
• 英文别名: Ethyl 3-[2-(3,3-dimethylbut-1-ynyl)phenyl]-3-oxopropanoate；ethyl 3-[2-(3,3-dimethylbut-1-ynyl)phenyl]-3-oxopropanoate
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: VFWBMGQVOCWUNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-碘噻吩 、 ethyl 3-(2-(3,3-dimethylbut-1-ynyl)phenyl)-3-oxopropanoate 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以35%的产率得到(Z)-ethyl 2-((E)-3-(2,2-dimethyl-1-(thiophen-2-yl)propylidene)isobenzofuran-1(3H)-ylidene)acetate
  参考文献：
  名称：

  Palladium(0)-catalyzed 5- exo - dig O -cyclization/coupling of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides to 1,3-dihydroisobenzofurans

  摘要：

  Palladium-catalyzed highly regioselective 5-exo-dig O-cyclization/coupling of a series of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides has been developed for the synthesis of (Z)-alkylidene-1,3-dihydroisobenzofuran derivatives. Reactions of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates and aryl iodides are carried out in DMSO at 80 degrees C with 5 mol % Pd(PPh3)(4) and 2 equiv of Et3N as a base for 4 h in modest yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.040
• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 、 ethyl 2-iodobenzoyl acetate 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 ethyl 3-(2-(3,3-dimethylbut-1-ynyl)phenyl)-3-oxopropanoate
  参考文献：
  名称：

  Palladium(0)-catalyzed 5- exo - dig O -cyclization/coupling of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides to 1,3-dihydroisobenzofurans

  摘要：

  Palladium-catalyzed highly regioselective 5-exo-dig O-cyclization/coupling of a series of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides has been developed for the synthesis of (Z)-alkylidene-1,3-dihydroisobenzofuran derivatives. Reactions of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates and aryl iodides are carried out in DMSO at 80 degrees C with 5 mol % Pd(PPh3)(4) and 2 equiv of Et3N as a base for 4 h in modest yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.040

文献信息

• Palladium(0)-catalyzed 5- exo - dig O -cyclization/coupling of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides to 1,3-dihydroisobenzofurans
  作者：Li-Lan Wei、Li-Mei Wei、Po-Yang Lin、Chin-Chau Chen、Wen-Bin Pan、Ming-Jung Wu

  DOI：10.1016/j.tetlet.2015.10.040

  日期：2015.11

  Palladium-catalyzed highly regioselective 5-exo-dig O-cyclization/coupling of a series of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates with aryl iodides has been developed for the synthesis of (Z)-alkylidene-1,3-dihydroisobenzofuran derivatives. Reactions of ethyl 3-(2-alkynylphenyl)-3-oxopropanoates and aryl iodides are carried out in DMSO at 80 degrees C with 5 mol % Pd(PPh3)(4) and 2 equiv of Et3N as a base for 4 h in modest yields. (C) 2015 Elsevier Ltd. All rights reserved.