2,2-dimethyl-5,8-dihydro-2H-1-benzopyran-5,8-dione | 132681-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,2-dimethyl-5,8-dihydro-2H-1-benzopyran-5,8-dione
• 英文别名: 5,8-dihydro-2,2-dimethyl-2H-1-benzopyran-5,8-dione；2,2-dimethyl-2H-chromene-5,8-dione；2,2-dimethylchromene-5,8-quinone；2,2-Dimethylchromene-5,8-dione
• CAS: 132681-14-2
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: JSQKKBGEOFZYPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,2-dimethyl-5,8-dihydro-2H-1-benzopyran-5,8-dione 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 22.5h， 生成 2,2-dimethyl-2H-pyrano[2,3-g]phthalazine-5,10-diol
  参考文献：
  名称：

  Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone

  摘要：

  A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.

  DOI：

  10.1021/acs.orglett.9b00090
• 作为产物：
  描述：

  4-((2-methylbut-3-yn-2-yl)oxy)phenol 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2,2-dimethyl-5,8-dihydro-2H-1-benzopyran-5,8-dione
  参考文献：
  名称：

  铬烯的研究。第9部分。苯二醌的合成

  摘要：

  描述了2，2-二甲基色烯-5，8-醌，2，2-二甲基色烯-6，7-醌和6，7-二甲氧基-2，2-二甲基色烯-5，8-醌的合成。这些化合物及其环氧乙烷衍生物易于被富电子的二烯生物还原，因此作为可能的抗肿瘤烷基化剂受到关注。

  DOI：

  10.1039/p19900002979

文献信息

• Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
  作者：Yasser Selim、Nabil Ouf、Mohamed Sakran

  DOI：10.3390/molecules180911485

  日期：——

  route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.

  天然双吡喃香豆素二戊内酯的结构已通过间苯二酚的明确合成路线得到证实。该序列由引入 3-氯-3-甲基丁-1-炔部分的吡喃环形成步骤引发。然后，预期产物经过 Fremy's 盐调节的氧化加成，然后闭环以产生双戊内酯。还发现双瓣内酯在携带 S180 的小鼠癌细胞系中具有免疫活性。
• SYNTHESIS OF 2,2-DIMETHYL-3, 4-EPOXY-2<b><i>H</i></b>-NAPHTHO[2,3-<i>b</i>]PYRAN-5, 10-DIONE
  作者：Ricardo A. Tapia、Claudia Lizama、Claudio López、Jaime A. Valderrama

  DOI：10.1081/scc-100000588

  日期：2001.1

  A short and convenient synthesis of benzopyranoquinone 6 and its application to the preparation of epoxynaphthopyanoquinone 1 is described.
• Zuloaga, Fernando; Tapia, Ricardo; Quintanar, Carmina, Journal of the Chemical Society. Perkin transactions II, 1995, # 5, p. 939 - 944
  作者：Zuloaga, Fernando、Tapia, Ricardo、Quintanar, Carmina

  DOI：——

  日期：——
• BROWN, PHILIP E.;LEWIS, ROBERT A.;WARING, MARK A., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N1, C. 2979-2988
  作者：BROWN, PHILIP E.、LEWIS, ROBERT A.、WARING, MARK A.

  DOI：——

  日期：——
• Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone
  作者：Simon D. Schnell、Anthony Linden、Karl Gademann

  DOI：10.1021/acs.orglett.9b00090

  日期：2019.2.15

  A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.