4-(furan-3-ylmethoxy)-but-2-ynoic acid methyl ester | 519157-23-4

• 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: 4-(furan-3-ylmethoxy)-but-2-ynoic acid methyl ester
• 英文别名: Methyl 4-(furan-3-ylmethoxy)but-2-ynoate
• CAS: 519157-23-4
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: QWEUBGISJCANIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  281.5±25.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(furan-3-ylmethoxy)-but-2-ynoic acid methyl ester 在 palladium on activated charcoal 、 palladium diacetate 氢气 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (6,7-dihydro-4H-furo[3,2-c]pyran-7-yl)acetic acid methyl ester
  参考文献：
  名称：

  Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.

  DOI：

  10.1021/ol034177k
• 作为产物：
  描述：

  3-呋喃甲醇 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.0h， 生成 4-(furan-3-ylmethoxy)-but-2-ynoic acid methyl ester
  参考文献：
  名称：

  Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.

  DOI：

  10.1021/ol034177k

文献信息

• Gold(I)-Catalyzed<i>endo</i>-Selective Intramolecular α-Alkenylation of β-Yne-Furans: Synthesis of Seven-Membered-Ring-Fused Furans and DFT Calculations
  作者：Zhe Dong、Cheng-Hang Liu、Yi Wang、Mu Lin、Zhi-Xiang Yu

  DOI：10.1002/anie.201306965

  日期：2013.12.23

  Alkenylation of furans: An efficient gold‐catalyzed endo‐selective intramolecular α‐alkenylation of β‐alkyne‐substituted furans has been developed to synthesize challenging seven‐membered‐ring‐fused furans in good to excellent yields. Preliminary DFT calculations have been carried out to understand the experimentally observed regioselectivity. DME=1,2‐dimethoxyethane, Ts=p‐toluenesulfonyl.

  呋喃的烯基：一个有效的金催化内切-选择性分子内β -炔基取代的呋喃的α烯基化已发展到合成具有挑战性良好7元环稠合的呋喃，以优异的产率。已经进行了初步的DFT计算以了解实验观察到的区域选择性。DME = 1,2-二甲氧基乙烷，Ts =对甲苯磺酰基
• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.
• Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation
  作者：Stefan J. Pastine、So Won Youn、Dalibor Sames

  DOI：10.1021/ol034177k

  日期：2003.4.1

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.