3-phenylnaphtho[1,2-b]furan-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 3-phenylnaphtho[1,2-b]furan-2(3H)-one
• 英文别名: 3-phenyl-3H-benzo[g][1]benzofuran-2-one
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: KNUJTYLGHLGQTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylnaphtho[1,2-b]furan-2(3H)-one 、 2-重氮基-2-苯基乙酸叔丁酯酯 在 di-μ-chlorobis(norbornadiene)dirhodium(I) 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 tert-butyl 2-(2-oxo-3-phenyl-2,3-dihydronaphtho[1,2-b]furan-3-yl)-2-phenylacetate
  参考文献：
  名称：

  Asymmetric Rh(I)-Catalyzed Functionalization of the 3-C(sp³)–H Bond of Benzofuranones with α-Diazoesters

  摘要：

  An asymmetric Rh(I)-catalyzed functionalization of the 3-C(sp(3))-H bond of benzofuranones with alpha-diazoesters has been developed, providing a new strategy for the stereoselective 3-alkylation of benzofuranones. With low catalyst loadings (low to 0.02 mol % Rh), a number of benzofuranones bearing consecutive quaternary and tertiary stereogenic centers have been synthesized (up to 94% yield, 95:5 dr, and >99% ee). The synthetic utilities of this methodology have been demonstrated by elaborating the model product 3aa to a series of enantiopure compounds with similarities to natural products and drug candidates.

  DOI：

  10.1021/acs.orglett.8b02555
• 作为产物：
  描述：

  methyl 2-(1-hydroxynaphthalen-2-yl)-2-phenylacetate 在 三氟乙酸 作用下， 反应 6.0h， 以99%的产率得到3-phenylnaphtho[1,2-b]furan-2(3H)-one
  参考文献：
  名称：

  铜和α-芳基-α-重氮酸酯对苯酚和萘酚的邻位选择性CH键进行铜催化官能化。

  摘要：

  在这里，我们报道了第一个铜催化的未保护的萘酚和苯酚与α-芳基-α-二重氮酯的高效C（sp 2）-H官能化。在此转化过程中，CuCl 2在温和条件下有效促进了高度化学和位点选择性的C–H键官能化，从易于获得的起始原料中以中等至优异的产率提供了多种酚衍生物。

  DOI：

  10.1039/d0cc04495d

文献信息

• A Convenient Palladium-Catalyzed Carbonylative Synthesis of Benzofuran-2(3 <i>H</i> )-ones with Formic Acid as the CO Source
  作者：Xinxin Qi、Hao-Peng Li、Xiao-Feng Wu

  DOI：10.1002/asia.201600873

  日期：2016.9.6

  A general and convenient palladium‐catalyzed carbonylation procedure for the synthesis of benzofuran‐2(3 H)‐ones from phenols and aldehydes has been developed. With formic acid as the CO source, a variety of benzofuran‐2(3 H)‐ones were obtained in moderate to good yields.

  已经开发了一种通用且方便的钯催化羰基化方法，用于从苯酚和醛类合成苯并呋喃-2（3  H）-酮。以甲酸作为一氧化碳源，可以中等至良好的收率获得各种苯并呋喃-2（3  H）-酮。
• Chiral Calcium Phosphate Catalyzed Enantioselective Amination of 3-Aryl-2-benzofuranones
  作者：Ruihan Liu、Suvratha Krishnamurthy、Zhenwei Wu、K. S. Satyanarayana Tummalapalli、Jon C. Antilla

  DOI：10.1021/acs.orglett.0c03059

  日期：2020.10.16

  4-tert-butyl-phenyl substituted (R)-[H8]-BINOL chiral calcium phosphate catalyzed enantioselective amination of 3-aryl-2-benzofuranones with dibenzyl azodicarboxylate is described. The catalyst loading of the reaction is 1 mol %. This transformation is facile and has a high degree atom economy, which gave products with good yields and high enantioselectivities (79% to 99%). This reaction has excellent ee

  描述了4-叔丁基-苯基取代的（R）-[H 8 ] -BINOL手性磷酸钙催化的3-芳基-2-苯并呋喃酮与偶氮二羧酸二苄酯的对映选择性胺化。反应的催化剂负载量是1mol％。这种转变是容易的，并且具有高度的原子经济性，这使得产物具有良好的产率和高对映选择性（79％至99％）。该反应具有优异的ee和较宽的底物范围以及温和的反应条件。
• Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
  作者：Zhunzhun Yu、Yongfeng Li、Peichao Zhang、Lu Liu、Junliang Zhang

  DOI：10.1039/c9sc01657k

  日期：——

  an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C–H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group

  在这里，开发了一种空前的配体和对阴离子控制的和位点选择性可转换的未保护的萘酚与α-芳基-α-二重氮酯的直接C–H键直接官能化。在该转化中，通过打开/关闭金属络合物与羟基之间的配位来实现位点选择性。初步机理表明，羟基与金催化剂之间的相互作用在切换金卡宾的位点选择性中起着关键作用。该协议可能为C–H键功能化提供一种新颖的设计。
• Enantioselective Amination of 3‐Substituted‐2‐benzofuranones via Non‐covalent N‐Heterocyclic Carbene Catalysis
  作者：Bhaskar Deb Mondal、Sadhan Gorai、Rounak Nath、Ankan Paul、Joyram Guin

  DOI：10.1002/chem.202303115

  日期：2024.1.22

  Herein, an efficient method for asymmetric α‐amination of 2‐benzofuranones with N‐heterocyclic carbene (NHC) catalysis is reported. The process is based on non‐covalent interaction of NHC with substrate, facilitating the formation of a chiral ion‐pair that encompasses enolate and azolium salt. The activated enolate adds to an electrophilic amine source with sufficient facial control to furnish an enantioenriched product having an amine substituted quaternary stereocenter. The process displays a broad substrate scope. A preparative scale synthesis has been achieved. Preliminary mechanistic investigations based on experimental and DFT studies suggest a reaction pathway that involves non‐covalent substrate/NHC interactions and essentially implicate the role of π‐π interaction in diastereomeric transition states for stereo‐chemical discrimination.

  摘要报告了一种利用 N-杂环碳烯（NHC）催化 2-苯并呋喃酮的不对称 α-氨基化的有效方法。该过程基于 NHC 与底物的非共价作用，促进了包含烯醇和偶氮鎓盐的手性离子对的形成。活化后的烯酸盐与亲电胺源相加，在足够的表面控制下生成具有胺取代的四元立体中心的对映体富集产物。该工艺具有广泛的底物范围。制备规模的合成已经实现。基于实验和 DFT 研究的初步机理调查表明，反应途径涉及非共价底物/NHC 相互作用，并从根本上揭示了非对映转换态中 π-π 相互作用在立体化学鉴别中的作用。
• Intramolecular Displacement of Carboxylate Ion. II. The Effect of Some Variations in Structure of Phenol-alcohols
  作者：Cyrus O. Guss

  DOI：10.1021/ja01146a033

  日期：1951.2