2-hydroxy-2-(thiophen-2-yl)naphtho[2,1-b]furan-1(2H)-one | 1574190-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-hydroxy-2-(thiophen-2-yl)naphtho[2,1-b]furan-1(2H)-one
• 英文别名: 2-Hydroxy-2-thiophen-2-ylbenzo[e][1]benzofuran-1-one；2-hydroxy-2-thiophen-2-ylbenzo[e][1]benzofuran-1-one
• CAS: 1574190-51-4
• 化学式: C₁₆H₁₀O₃S
• 分子量: 282.32
• InChiKey: CDUQKWFPHJWXCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基噻吩 、 2-萘酚 在 碘 、 二甲基亚砜 作用下， 反应 48.0h， 以70%的产率得到2-hydroxy-2-(thiophen-2-yl)naphtho[2,1-b]furan-1(2H)-one
  参考文献：
  名称：

  I₂-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-b]furan-1(2H)-ones with a Quaternary Center

  摘要：

  A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel-Crafts/oxidation/cyclization mechanism was proposed.

  DOI：

  10.1021/ol5004093

文献信息

• 10.1039/d4ob00693c
  作者：Hemamalini, Vijayakumar、Shanthi, Markabandhu、Shankar, Bhaskaran、Dandela, Rambabu、Perumal, Karuppaiah、Ramesh, Subburethinam

  DOI：10.1039/d4ob00693c

  日期：——

  A highly efficient and innovative method involving base-mediated oxidative annulation between 2-naphthols and phenylglyoxal monohydrate under visible light irradiation has been successfully developed. This method leads to the formation of oxygen-containing heterocyclic compounds, particularly hydroxy-naphthofuranone derivatives, encompassing a unique quaternary carbon center. An X-ray diffraction study

  已经成功开发出一种高效且创新的方法，涉及在可见光照射下 2-萘酚和一水合苯基乙二醛之间的碱介导氧化成环。该方法导致形成包含独特季碳中心的含氧杂环化合物，特别是羟基萘呋喃酮衍生物。 X 射线衍射研究明确证实了此类衍生物的结构。特别是，该反应中的水分子充当溶剂、试剂和添加剂等多种功能，并且发现该过程的转化率受到存在的水体积的影响。这种原子经济的方法表现出对苯基乙二醛一水合物和2-萘酚中不同取代基的耐受性，能够以令人满意的收率合成各种萘并呋喃酮。在酸性环境下形成萘呋喃阳离子中间体，能够与多种芳香族或醇类亲核伙伴形成 C-C 或 C-O 键。此外，从这些萘并呋喃酮衍生物中鉴定和生成频哪醇型起始前体使得能够合成高度区域选择性的萘并呋喃衍生物。
• I₂-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-<i>b</i>]furan-1(2<i>H</i>)-ones with a Quaternary Center
  作者：Qinghe Gao、Xia Wu、Shan Liu、Anxin Wu

  DOI：10.1021/ol5004093

  日期：2014.3.21

  A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel-Crafts/oxidation/cyclization mechanism was proposed.