1-(5-methyl-2-furyl)ethyl propargyl ether | 99758-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-(5-methyl-2-furyl)ethyl propargyl ether
• 英文别名: 2-methyl-5-[(prop-2-yn-1-yloxy)methyl]furan；2-methyl-5-(1-(prop-2-ynyloxy)ethyl)furan；2-Methyl-5-(1-prop-2-ynoxyethyl)furan
• CAS: 99758-24-4
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: SQHCHQWOAVEUPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-methyl-2-furyl)ethyl propargyl ether 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以95%的产率得到1,5-Dimethyl-4,5-dihydro-isobenzofuran-5-ol
  参考文献：
  名称：

  呋喃通过丙二烯中间体的分子内Diels-Alder反应的新型环转移反应：新的双环化反应

  摘要：

  通过串联分子内Diels-Alder反应和加合物的碱催化开环，已经开发了呋喃向稠合呋喃的新型环转移反应。

  DOI：

  10.1016/s0040-4039(00)98138-3
• 作为产物：
  描述：

  2-甲基呋喃 在 正丁基锂 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 14.0h， 生成 1-(5-methyl-2-furyl)ethyl propargyl ether
  参考文献：
  名称：

  Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers: High Effect of the Chain Length on the Structure and Reactivity of the Cycloadducts

  摘要：

  The structure and reactivity of the cycloadducts of the title reaction were found to be highly dependent on the chain length between the furan diene and the allenyl ether dienophile. Reaction of the propargyl ether (2) with t-BuOK in t-BuOH at 85-degrees-C for 3 h gave a mixture of the cycloadducts (3) and (4) in 90% yield, which were transferred to the benzo derivatives (5), (6) and (7). Treatment of the propargyl ether (8) with t-BuoK in t-BuOH at 85-degrees-C for 5 h gave the products (9) and (10) in a ratio of 8:1 in 65% yield, no detectable amount of the cycloadduct (8b) was obtained. Refluxing of the propargyl ether (13) with t-BuOK in t-BuOH at 85-degrees-C for 4 h gave the allenyl ether (14). Heating 14 in DMSO at 15-degrees-C for 12 h still did not give 15.

  DOI：

  10.3987/com-94-6675

文献信息

• Mechanistic Investigations of a Stable, Highly Active, Extremely Sterically Shielded Molecular Gold Catalyst
  作者：Simone G. Weber、David Zahner、Frank Rominger、Bernd F. Straub

  DOI：10.1002/cctc.201200944

  日期：2013.8

  An N‐heterocyclic carbene gold complex IPr**AuNTf2 has been synthesized, spectroscopically investigated, structurally characterized, and used as a highly active and stable catalyst in the Hashmi phenol synthesis (IPr**=1,3‐di‐p‐tolylimidazol‐2‐ylidene with four di‐tert‐butylbenzhydryl ortho substituents, Tf=trifluoromethansulfonyl). A side reaction comprises an irreversible arene oxide ring opening

  N杂环卡宾金络合物IPr ** AuNTf 2已被合成，光谱研究，结构表征并用作Hashmi苯酚合成中的高活性和稳定催化剂（IPr ** = 1,3- di - p - tolylimidazol带有两个二叔丁基苯甲基邻位的-2-亚烷基取代基，Tf ＝三氟甲磺酰基）。副反应包括不可逆的氧化芳烃开环，随后发生1,2，甲基转移。较高的阳离子金物质平衡浓度，对无活性双核中间体的规避和催化剂分解途径的抑制解释了辅助配体的空间需求的优势。炔烃的甲醇加成-水合反应具有烯基金催化剂静止状态的周转限制质子转移步骤，这由较大的主要动力学同位素效应和炔烃竞争实验所表明。
• Intramolecular azavinyl carbene-triggered rearrangement of furans
  作者：Anton S. Makarov、Maxim G. Uchuskin、A. Stephen K. Hashmi

  DOI：10.1039/c9sc02299f

  日期：——

  An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting

  已经探索了 1-甲苯磺酰基-1,2,3-三唑与呋喃的分子内铑催化反应。研究发现，甲苯磺酰亚氨基官能团在参与关键反应中间体随后的多米诺骨牌转化中发挥着重要的化学作用。其中一种反应途径产生有价值的2-甲酰基-和2-乙酰基吡啶结构单元，这些结构单元可以从容易获得的(呋喃-2-基甲基)炔丙胺开始一锅获得。提出了一种从所得吡啶合成高功能化中氮茚的原始方法。
• Interrupted Furan–Yne Cyclization: Access to Unsaturated Dicarbonyl Compounds and Their Subsequent Transformation into Functionalized Pyridazines
  作者：Yury A. Vasev、Ekaterina R. Nasibullina、Anton S. Makarov、Maxim G. Uchuskin

  DOI：10.1021/acs.orglett.3c02794

  日期：2023.11.3

  The key carbenoid intermediate of transition-metal-catalyzed furan–yne cyclization in Hashmi phenol synthesis could be efficiently intercepted with water under the developed reaction conditions in order to provide access to functionalized unsaturated dicarbonyl compounds that might serve as convenient precursors for the straightforward synthesis of annulated pyridazines.

  在所开发的反应条件下，哈希米苯酚合成中过渡金属催化的呋喃-炔环化的关键类胡萝卜素中间体可以有效地与水拦截，从而提供官能化不饱和二羰基化合物，这些化合物可以作为直接合成环状哒嗪。
• 1,2,3-Triazole as a Special “X-Factor” in Promoting Hashmi Phenol Synthesis
  作者：Yunfeng Chen、Wuming Yan、Novruz G. Akhmedov、Xiaodong Shi

  DOI：10.1021/ol902680k

  日期：2010.1.15

  P-31 NMR experiments revealed rapid decomposition of the Ph3PAu+TfO- complex in the presence of the furan-yne, which resulted in poor reactivity as reported in the literature. Therefore, Instead of tuning different ligands (PR3), the 1,2,3-triazole was applied as a special X-factor to stabilize the catalyst. The desired phenol products were prepared in excellent yields (1% cat. up to 95% yield) and chemoselectivity (>20:1).
• Wu Hsien-Jen, Lin Shie-Hsiung, Lin Chu-Chung, Heterocycles, 38 (1994) N 7, S 1507-1518
  作者：Wu Hsien-Jen, Lin Shie-Hsiung, Lin Chu-Chung

  DOI：——

  日期：——