萘并[2,1-b]呋喃-2(1H)-酮 | 4352-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 中文名称: 萘并[2,1-b]呋喃-2(1H)-酮
• 英文名称: 1H-naphtho[2,1-b]furan-2-one
• 英文别名: naphtha[2,1-b]furan-2(1H)-one；naphtho[2,1-b]furan-2(1H)-one；1H-naphtho[2,1-b]furan-2-one；1H-Naphtho[2,1-b]furan-2-on；1H-benzo[e][1]benzofuran-2-one
• CAS: 4352-63-0
• 化学式: C₁₂H₈O₂
• mdl: MFCD08443985
• 分子量: 184.194
• InChiKey: KVLORZFYGDNPIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106°C
• 溶解度：
  0.00 M

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  萘并[2,1-b]呋喃-2(1H)-酮 在 正丁基锂 、 sodium acetate 、 乙酸酐 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 生成 (Z)-2-(2-hydroxy-naphthalen-1-yl)-3-phenyl-N-((R)-1-phenyl-ethyl)-acrylamide
  参考文献：
  名称：

  2-(2-Hydroxyaryl)cinnamic amides: a new class of axially chiral molecules

  摘要：

  The syntheses of several differently substituted amides formally derived from a chiral amine, either E-2-(2-hydroxyphenyl)cinnamic acid or both E- and Z-2-(2-hydroxynaphthyl)cinnamic acid, are reported. These molecules display a restricted rotation about the C-2-(aryl) bond. The barriers to rotation about the C-2-(aryl) bond were measured by the dynamic H-1 NMR and were found to vary between 11.8 and 24.5 kcal mol(-1), depending on the substitution. In particular, E-2-(2-hydroxynapthyl)cinnamic amides, displayed a high barrier to rotation (Delta G(c)(double dagger)= 24.4 kcal mol(-1)) and could be isolated in both diastereomerically pure forms at room temperature. The X-ray structure of one E-2-(2-hydroxynapthyl)cinnamic amide, was resolved, enabling for the determination of the absolute configuration of the chiral axis (aR). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.019
• 作为产物：
  描述：

  N,N-diethyl-2-(2-hydroxynaphthalen-1-yl)acetamide 在 溶剂黄146 作用下， 反应 20.0h， 以85%的产率得到萘并[2,1-b]呋喃-2(1H)-酮
  参考文献：
  名称：

  Anionic Homologous Fries Rearrangement of O-(2-Methylaryl)carbamates. A Regiospecific Route to Benzo[b]furan-2(3H)-ones including an Unnamed Metabolite from Helenium Species

  摘要：

  一种新的 LDA 介导的 O → C 氨基甲酰基迁移 3 为芳基乙酰胺 5（苯并呋喃酮和萘并呋喃酮 7 的前体）提供了一条普遍而有效的途径，其中一种芳基乙酰胺 5 可作为简短合成从几种 Helenium 植物中分离出来的天然苯并呋喃内酯 11 的起始原料。

  DOI：

  10.1055/s-1997-5743

文献信息

• Pd(OAc)₂-catalyzed Lactonization of Arylacetamides Involving Oxidation of C–H Bonds
  作者：Takeshi Uemura、Takuya Igarashi、Moe Noguchi、Kaname Shibata、Naoto Chatani

  DOI：10.1246/cl.150041

  日期：2015.5.5

  The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactone...

  含有喹啉-8-基甲胺作为导向基团的芳基乙酰胺与PhI(OAc)2在Pd(OAc)2作为催化剂存在下发生内酯化反应得到γ-内酯...
• Metal-Free Oxidative Cyclization of Alkynyl Aryl Ethers to Benzofuranones
  作者：Katharina Graf、Carmen L. Rühl、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201304813

  日期：2013.11.25

  Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N‐oxide as an oxidant and catalytic amounts of a Brønsted acid to provide benzofuranones. If non‐terminal alkynyl ethers are applied, a 1,2‐hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α‐oxy carbene precursors even in the absence of a metal catalyst

  易获得的苯酚可以转化为取代的芳基炔基醚，它们与N-氧化物作为氧化剂和催化量的布朗斯台德酸反应生成苯并呋喃酮。如果使用非末端炔基醚，则会发生1,2-氢化物转变，从而获得丙烯酸苯酯。因此，即使在没有金属催化剂的情况下，活化的炔烃也可以用作α-氧卡宾的前体。
• [EN] ARYL NAPHTHALIDE LIGNANS AS ANTI-HIV AGENTS<br/>[FR] LIGNANES DE NAPHTALIDE D'ARYLE EN TANT QU'AGENTS ANTI-VIH
  申请人：UNIV ILLINOIS

  公开号：WO2013019662A1

  公开（公告）日：2013-02-07

  Provided herein are glycosidic aryl naphthalide lignans compounds, such as justiprocumin A isolated from the plant Justicia gendarussa Burm.f. (Acanthaceae), which are effective in the treatment of AIDS and HIV infections.

  本文提供了一种叫做justiprocumin A的糖苷基芳基萘木脂素化合物，它们是从龙胆草（Justicia gendarussa Burm.f.，爵床科）中分离出来的，对治疗艾滋病和HIV感染有效。
• Preparation and Stereochemistry of the Isopropylidene Derivatives of 1,2‐Dihydronaphtho[2,1‐<i>b</i>]Furan‐1,2‐Diol and 1,2,9,10‐Tetrahydronaphtho[2,1‐<i>b</i>:7,8‐<i>b</i>′] Difuran‐1,2,9,10‐Tetraol in Comparison with the Corresponding Acetyl Derivatives
  作者：Makoto Yamaye、Yoshiko Motoyanagi、Aya Nakagawa、Sanae Kametani、Tetsutaro Yoshinaga、Namiko Cho (Toh)、Xiaobo Fan、Taketoshi Kito

  DOI：10.1081/scc-200039376

  日期：2004.12.31

  10‐tetrahydronaphtho[2,1‐b:7,8‐b′]difuran‐1,2,9,10‐tetraol were transformed into the corresponding isopropylidene derivatives, which were studied mainly by 1H NMR and chiral HPLC analyses in terms of a possible transformation mechanism and stereochemistry in comparison with their corresponding acetyl derivatives.

  摘要 1,2-Dihydronaphtho[2,1-b]furan-1,2-diol 和 1,2,9,10-tetrahydronaphtho[2,1-b:7,8-b']difuran-1,2, 9,10-四醇转化为相应的异亚丙基衍生物，主要通过 1H NMR 和手性 HPLC 分析研究其可能的转化机制和立体化学，并与其相应的乙酰衍生物进行比较。
• SKIN LIGHTENING COMPOSITION
  申请人：Bella Aurora Labs, S.A.

  公开号：EP3791932A1

  公开（公告）日：2021-03-17

  The present invention relates to a cosmetic skin lightening composition comprising the combination of sclareolide, kojic acid and ascorbyl glucoside, wherein kojic acid is encapsulated within a targeted microcapsule or nanocapsule having a melanocortin 1 receptor (MC1R) agonist peptide bound to the surface. It was found that such combination of active substances provided synergistic skin-whitening effect. The present invention also relates to the cosmetic use of this composition for skin whitening, particularly, for the elimination or reduction of hyperpigmented marks of the skin, such as UV exposure related marks, post-scar marks, post-inflammation marks, melasma marks, lentigo marks or age-related marks.

  本发明涉及一种化妆品美白组合物，该组合物包含香紫苏内酯、曲酸和抗坏血酸葡萄糖苷，其中曲酸被封装在靶向微胶囊或纳米胶囊中，该微胶囊或纳米胶囊表面结合有黑色素皮质素 1 受体（MC1R）激动剂肽。研究发现，这种活性物质组合具有协同美白效果。本发明还涉及将这种组合物用于皮肤美白的美容用途，特别是用于消除或减少皮肤的色素沉着印记，如紫外线照射相关印记、疤痕后印记、炎症后印记、黄褐斑印记、雀斑印记或与年龄相关的印记。