1-Benzo[1,3]dioxol-5-yl-4,5-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylic acid dimethyl ester | 76886-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Benzo[1,3]dioxol-5-yl-4,5-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1-(1,3-benzodioxol-5-yl)-4,5-dimethoxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate
• CAS: 76886-72-1
• 化学式: C₂₃H₂₀O₉
• 分子量: 440.406
• InChiKey: XXPMXCNVLPWTJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-Benzo[1,3]dioxol-5-yl-4,5-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylic acid dimethyl ester 生成 5-(5,6-Dimethoxy-isobenzofuran-1-yl)-benzo[1,3]dioxole
  参考文献：
  名称：

  Electron impact mass spectra of isobenzofurans, isonaphthofurans and some of their Diels-Alder adducts

  摘要：

  AbstractThe mass spectra of a wide variety of substituted isobenzofurans (IBF) have been studied by the direct examination of stable IBFs and IBF ions formed in the retro‐Diels–Alder cleavage of oxabicyclo adducts. In general, the fragmentation patterns observed are very dependent upon the nature and position of substitution. The dimethyl acetylenedkarboxylate adducts also show additional interesting and novel fragmentation pathways that are not IBF related.

  DOI：

  10.1002/oms.1210231102
• 作为产物：
  描述：

  2-碘-4,5-二甲氧基苯甲醛 在 sodium tetrahydroborate 、 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 0.5h， 生成 1-Benzo[1,3]dioxol-5-yl-4,5-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Anionic Fries rearrangements of esters of ortho-iodobenzyl alcohols: rapid routes to oestrone methyl ether and its 9? epimer, and aryl naphthalide lignans

  摘要：

  通过锂-碘交换引发的快速、通用、低温邻碘苄酯重排反应，生成异苯并呋喃，随后通过分子间和分子内迪尔斯-阿尔德（IMDA）反应当场截获，生成多种碳环化合物，包括天然木脂素和甾体。

  DOI：

  10.1039/c39920000164

文献信息

• Keay, Brian A.; Plaumann, Heinz P.; Rajapaksa, Dayananda, Canadian Journal of Chemistry, 1983, vol. 61, p. 1987 - 1995
  作者：Keay, Brian A.、Plaumann, Heinz P.、Rajapaksa, Dayananda、Rodrigo, Russell

  DOI：——

  日期：——
• KEAY, B. A.;PLAUMANN, H. P.;RAJAPAKSA, D.;RODRIGO, R., CAN. J. CHEM., 1983, 61, N 9, 1987-1995
  作者：KEAY, B. A.、PLAUMANN, H. P.、RAJAPAKSA, D.、RODRIGO, R.

  DOI：——

  日期：——
• Anionic Fries rearrangements of esters of ortho-iodobenzyl alcohols: rapid routes to oestrone methyl ether and its 9? epimer, and aryl naphthalide lignans
  作者：Stephen Horne、Russell Rodrigo

  DOI：10.1039/c39920000164

  日期：——

  A fast, general, low-temperature rearrangement of ortho-iodobenzyl esters, triggered by lithium–iodine exchange, leads to isobenzofurans which are intercepted in situ by inter and intramolecular Diels–Alder (IMDA) reactions to produce a variety of carbocycles including natural lignans and steroids.

  通过锂-碘交换引发的快速、通用、低温邻碘苄酯重排反应，生成异苯并呋喃，随后通过分子间和分子内迪尔斯-阿尔德（IMDA）反应当场截获，生成多种碳环化合物，包括天然木脂素和甾体。
• Electron impact mass spectra of isobenzofurans, isonaphthofurans and some of their Diels-Alder adducts
  作者：Peter W. Dibble、Russell Rodrigo

  DOI：10.1002/oms.1210231102

  日期：1988.11

  AbstractThe mass spectra of a wide variety of substituted isobenzofurans (IBF) have been studied by the direct examination of stable IBFs and IBF ions formed in the retro‐Diels–Alder cleavage of oxabicyclo adducts. In general, the fragmentation patterns observed are very dependent upon the nature and position of substitution. The dimethyl acetylenedkarboxylate adducts also show additional interesting and novel fragmentation pathways that are not IBF related.