4,5-methylenedioxyhomophthalic anhydride | 28281-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,5-methylenedioxyhomophthalic anhydride
• 英文别名: 8H-[1,3]dioxolo[4,5-g]isochromene-5,7-dione；8H-[1,3]Dioxolo[4,5-g]isochromen-5,7-dion；4,5-Methylendioxy-homophthalsaeure-anhydrid；4,5-Methylendioxy-homophthalsaeureanhydrid；5H-1,3-Dioxolo[4,5-g][2]benzopyran-5,7(8H)-dione；8H-[1,3]dioxolo[4,5-g]isochromene-5,7-dione
• CAS: 28281-86-9
• 化学式: C₁₀H₆O₅
• 分子量: 206.155
• InChiKey: IGYYLNWLNBKSIK-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-methylenedioxyhomophthalic anhydride 在 盐酸 、 氢氧化钾 、 copper bronze 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 二氯甲烷 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.25h， 生成 去氢石蒜碱酮
  参考文献：
  名称：

  Synthesis of Antitumor Lycorines by Intramolecular Diels−Alder Reaction

  摘要：

  Pharmacologically interesting lycorines were obtained by a short, efficient method based on an intramolecular Diels-Alder reaction between an alpha-pyrone and an alkyne, followed by loss of CO2 in a retro Diels-Alder reaction. The cyclization precursors (pyrones 9) were obtained in good yields in two or three steps from the corresponding homophthalic acid or anhydride.

  DOI：

  10.1021/jo9518415
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙酰氯 作用下， 生成 4,5-methylenedioxyhomophthalic anhydride
  参考文献：
  名称：

  Stevens; Wilson, Journal of the Chemical Society, 1928, p. 2828

  摘要：

  DOI：

文献信息

• Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of <i>N</i>-Sulfonyl Imines and Cyclic Anhydrides
  作者：Stephen W. Laws、Lucas C. Moore、Michael J. Di Maso、Q. Nhu N. Nguyen、Dean J. Tantillo、Jared T. Shaw

  DOI：10.1021/acs.orglett.7b00468

  日期：2017.5.19

  A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.

  报道了非对映选择性的碱催化的环状可烯醇化酸酐和N-磺酰基亚胺的曼尼希反应，用于合成δ-内酰胺。该酸酐曼尼希反应可耐受衍生自芳基和可烯化醛的亚胺。碱催化的产物差向异构途径可确保在芳基和非手性可烯化亚胺中具有很高的非对映选择性。
• A highly stereoselective synthesis of 3,4-dihydro-1(2H)-isoquinolinones and 8-oxoberbines from homophthalic anhydrides and azomethines
  作者：M.A. Haimova、N.M. Mollov、S.C. Ivanova、A.I. Dimitrova、V.I. Ognyanov

  DOI：10.1016/0040-4020(77)80114-2

  日期：1977.1

  The interaction between 1,3-isochromanediones(homophthalic anhydrides) 1 and acyclic azomethines of types 2 and 3 and the cyclic 6,7-dimethoxy-3,4-dihydroisoquinoline 4 is investigated. The former lead in high yields to the (±)-trans-3-aryl-4-carboxy-3,4-dihydro-1(2H)-isoquinolinones 5, while the latter gives the (±)-cis-13-carboxy-8-oxoberbines 7. The relative configurations of compounds 5–8 as well

  研究了1，3-异二氰基二阴离子（均苯二酸酐）1与2和3型无环甲亚胺与环状6,7-二甲氧基-3,4-二氢异喹啉4的相互作用。以高产率的（±）前铅-反式的3-芳基-4-羧基-3,4-二氢- 1（2 ħ）异喹啉酮5，而后者使（±） -顺-13-羧基8-氧代苯丁二烯7。化合物5-8的相对构型，以及某些5型化合物和所有6型化合物的优选构象是通过化学相关性和NMR确定的。
• Synthesis of Antitumor Lycorines by Intramolecular Diels−Alder Reaction
  作者：Dolores Pérez、Gema Burés、Enrique Guitián、Luis Castedo

  DOI：10.1021/jo9518415

  日期：1996.1.1

  Pharmacologically interesting lycorines were obtained by a short, efficient method based on an intramolecular Diels-Alder reaction between an alpha-pyrone and an alkyne, followed by loss of CO2 in a retro Diels-Alder reaction. The cyclization precursors (pyrones 9) were obtained in good yields in two or three steps from the corresponding homophthalic acid or anhydride.
• Stevens; Wilson, Journal of the Chemical Society, 1928, p. 2828
  作者：Stevens、Wilson

  DOI：——

  日期：——