3,4-dihydro-1H-1,5-epoxybenzo[c]oxocine | 1042369-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4-dihydro-1H-1,5-epoxybenzo[c]oxocine
• 英文别名: 12,13-Dioxatricyclo[7.3.1.02,7]trideca-2,4,6,8-tetraene；12,13-dioxatricyclo[7.3.1.02,7]trideca-2,4,6,8-tetraene
• CAS: 1042369-71-0
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: WPGVTLLUNMHGCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-hydroxybut-1-yn-1-yl)benzaldehyde 在 gold(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到3,4-dihydro-1H-1,5-epoxybenzo[c]oxocine
  参考文献：
  名称：

  金催化的2-（Ynol）芳基醛的级联环化：苯并苯并烷和苯并双环[ n .3.1]缩醛的简便合成

  摘要：

  研究了金催化的2-（ynol）芳基醛的反应。当使用AuCl 3作为催化剂时，从反应中获得苯并二氢吡喃，而当使用三唑-金作为催化剂时，则生成苯并双环[ n .3.1]缩醛。讨论了可能的机制。

  DOI：

  10.1021/ol101985d

文献信息

• Intramolecular oxypalladation-initiated domino sequence: One-pot, two-step regioselective synthesis of isoquinolines
  作者：Perumal Vinoth、Muthu Karuppasamy、Anish Gupta、Subbiah Nagarajan、C. Uma Maheswari、Vellaisamy Sridharan

  DOI：10.1016/j.tet.2023.133272

  日期：2023.3

  A palladium-catalyzed one-pot, two-step sequential reaction of 2-alkynylarylaldehydes and ketones was established to access isoquinolines under mild conditions. The initial palladium-triggered 6-endo-dig cyclization-hydration-ring opening sequence afforded the 1,5-dicarbonyl compounds and the subsequent annulation in the presence of ammonium acetate delivered the isoquinoline derivatives in good to

  建立了钯催化的 2-炔基芳基醛和酮的一锅两步连续反应，以在温和条件下获得异喹啉。最初的钯引发的 6-内切环化-水合-开环序列提供了 1,5-二羰基化合物，随后在乙酸铵存在下环化以良好至优异的收率（高达 97%）提供异喹啉衍生物在很短的反应时间内。带有侧链羟基和氨基官能团的具有挑战性的炔烃在以良好的收率获得相应的异喹啉方面显示出显着的反应性。开发的多米诺骨牌序列具有高度区域选择性，完全避开了竞争性 5- exo - dig导致茚酮的环化不同于金催化的文献先例。
• Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes
  作者：Monica Dell’Acqua、Brunilde Castano、Clara Cecchini、Tommaso Pedrazzini、Valentina Pirovano、Elisabetta Rossi、Alessandro Caselli、Giorgio Abbiati

  DOI：10.1021/jo5002559

  日期：2014.4.18

  The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(1) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth H-1 NMR experiments and an aimed "trapping" experiment.
• Synthesis of 1H-isochromen-1-ylphosphonates via AgOTf-catalyzed reaction of 2-alkynylbenzaldehyde with diethyl phosphite
  作者：Xingxin Yu、Qiuping Ding、Weizi Wang、Jie Wu

  DOI：10.1016/j.tetlet.2008.05.009

  日期：2008.7

  Tandem cyclization-addition reaction of 2-alkynylbenzaldehyde with diethyl phosphite catalyzed by AgOTf at room temperature was developed, which afforded the desired 1H-isochromen-1-ylphosphonates in moderate to good yields. (C) 2008 Elsevier Ltd. All rights reserved.