3,4-dihydrospiro-2',5'-dione | 75116-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydrospiro-2',5'-dione
• 英文别名: 6,7-benzo-1-oxaspiro<5.4>deca-6,8-diene-2,10-dione；2’H,3H-spiro[furan-2,1’-naphthalene]-2’,5(4H)-dione；2′H,3H-spiro[furan-2,1′-naphthalene]-2′,5(4H)-dione；2'H,3H-spiro[furan-2,1'-naphthalene]-2',5(4H)-dione；3,4-dihydrospiro[furan-2(5H),1'(2'H)-naphthalene]-2',5-dione；Spiro[naphthalene-1,5'-oxolane]-2,2'-dione
• CAS: 75116-43-7
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: KBKXSLSPGFSTCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydrospiro-2',5'-dione 在 盐酸 、 lithium aluminium tetrahydride 、 氨 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 33.5h， 生成 cis-5,8,9,11,12,16b-hexahydro-14,15-dimethoxy-6H,7H-benzonaphtho<2,1-b>pyrrolo<1,2-a>-azepine
  参考文献：
  名称：

  杂环螺萘。第六部分 与螺[萘-2（1 H），2'-吡咯烷] -1,5'-二酮的某些反应生成各种6、7、8、9、10和11元氮杂环烷烃† ‡

  摘要：

  将螺内酰胺5还原为螺-[萘，吡咯烷] 7，将其N-芳烷基化，得到9和17。环化9得到菲啶10和11 ; 同样，17提供7和8元杂环18和19。当进行分子内霍夫曼消除时，化合物10、18和19分别产生9元，10元和11元环系统，分别为16、22和23。

  DOI：

  10.1002/hlca.19800630705
• 作为产物：
  描述：

  3-(2-甲氧基-1-萘基)丙酸 在 三氟化硼乙醚 、 thallium(III) trifluoroacetate 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 0.01h， 以18%的产率得到3,4-dihydrospiro-2',5'-dione
  参考文献：
  名称：

  Thallium in organic synthesis. 61. Intramolecular capture of radical cations from thallium(III) trifluoroacetate oxidation of arylalkanoic acids and arylalkanols. New routes to oxygen heterocycles

  摘要：

  DOI：

  10.1021/ja00413a013

文献信息

• Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives
  作者：Muhammet Uyanik、Takeshi Yasui、Kazuaki Ishihara

  DOI：10.1021/acs.joc.7b01941

  日期：2017.11.17

  Highly enantioselective oxidative dearomatization of 2-naphthol derivatives was achieved for the first time by using conformationally flexible organoiodine catalysts derived from 2-aminoalcohol as a chiral source. Moreover, with the use of these catalysts, excellent enantioselectivities were also achieved for 1-naphthol derivatives, which had previously been obtained with only lower enantioselectivities

  通过使用衍生自2-氨基醇的构象柔性有机碘催化剂作为手性来源，首次实现了2-萘酚衍生物的高度对映选择性氧化脱芳香化作用。此外，通过使用这些催化剂，对于1-萘酚衍生物也获得了优异的对映选择性，以前仅以较低的对映选择性获得了1-萘酚衍生物。此外，从本反应获得的产物可以高产率和优异的立体选择性转化为高度官能化的螺内酯。
• Practical Oxidative Dearomatization of Phenols with Sodium Hypochlorite Pentahydrate
  作者：Muhammet Uyanik、Niiha Sasakura、Mitsuyoshi Kuwahata、Yasukazu Ejima、Kazuaki Ishihara

  DOI：10.1246/cl.141130

  日期：2015.3.5

  A highly efficient and practical oxidative dearomatization of phenols using sodium hypochlorite pentahydrate as an inexpensive, strong oxidant is reported for the first time. The oxidation reactions proceeded very rapidly in the presence of water to give the desired products in excellent yields, and sodium chloride and water were the only by-products derived from the oxidant.

  本研究首次报道了利用五水次氯酸钠作为廉价的强氧化剂对苯酚进行高效实用的氧化脱芳烃反应。氧化反应在有水存在的情况下进行得非常迅速，能以极高的产率得到所需的产物，氯化钠和水是氧化剂产生的唯一副产物。
• Phenyl trimethyl ammonium tribromide mediated robust one-pot synthesis of spiro-oxacycles – an economic route – stereoselective synthesis of oxaspirohexacyclodieneones
  作者：Debayan Sarkar、Manoj Kumar Ghosh、Nilendri Rout

  DOI：10.1039/c6ob01116k

  日期：——

  This paper entails the first recognition of Phenyl Trimethyl Ammonium Tribromide (PTAB) as an effective reagent for spiro-cyclizations proceeding via oxidative dearomatization. The experiment exhibits economical, metal and ligand free one-pot accomplishment of these significant transformations. The described protocol presents the first generalised methodology of spiro-oxacycle synthesis which can be

  本文首先认识到苯基三甲基三溴化铵（PTAB）是通过氧化脱芳香化作用进行螺环化的有效试剂。该实验展示了这些重要转化的经济，无金属和无配体一锅式完成。所描述的协议提出了螺-氧杂环合成的第一种通用方法，可以应用于各种方向。已经完成了对氧-螺环恶二烯酮的立体选择性合成。
• Heterocyclic spiro-naphthalenones. Part IV. Synthesis of some 3,4-dihydrospiro [naphthalene-2(1H),2?-pyrrolidine]-1-ols from 3,4-dihydrospiro [furan-2(5H),1?(2?H)-naphthalene]-2?,5-dione
  作者：Daniel Berney、Karlheinz Schuh

  DOI：10.1002/hlca.19800630420

  日期：1980.6.6

  Depending on the experimental conditions the spirolactone 3 on treatment with methylamine gave compounds 6, 7 or the rearranged product 4. Compound 4 was used to prepare the title compounds 11–13, 15, 18–20 and other derivatives.

  取决于实验条件，用甲胺处理的螺内酯3得到化合物6、7或重排产物4。化合物4用于制备标题化合物11-13、15、18-20和其他衍生物。
• Ammonium Hypoiodite-Catalyzed Peroxidative Dearomatization of Phenols
  作者：Kazuaki Ishihara、Muhammet Uyanik、Kohei Nishioka

  DOI：10.3987/com-16-s(s)84

  日期：——

  Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.