4-oxatetracyclo<5.4.2.02,608,11>trideca-9,12-diene | 5773-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 4-oxatetracyclo<5.4.2.02,608,11>trideca-9,12-diene
• 英文别名: 4-oxatetracyclo<5.4.2.0^2,60^8,11>trideca-9,12-diene
• CAS: 5773-44-4
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: HXRNLYYZTBREBH-CJXDBHJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-oxatetracyclo<5.4.2.02,608,11>trideca-9,12-diene 在 臭氧 、 二甲基硫 、 amberlyst-15 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以10%的产率得到5,12,14,16,17-pentaoxahexacyclo[9.5.1.0^2,10.0^3,7.0^8,15.0^9,13]heptadecane
  参考文献：
  名称：

  Oxa Bowls:  Studies Toward Hexaoxa-[6]-peristylane. Synthesis of a Seco-Derivative of Hexaoxa-[6]-peristylane

  摘要：

  When the concept of equivalency of all-cis-[n]-formyl-[n]-cycloalkanes with [n]-oxa-[n]-peristylanes was followed, an approach to the "oxa bowl" hexaoxa-[6]-peristylane 4a was delineated. This required an access to all-cis-cyclohexane-hexacarbaldehyde 5, which could be subjected to a 6-fold intramolecular acetalization cascade. A readily available Diels-Alder adduct of cyclooctatetraene and maleic anhydride was chosen as the starting material and was elaborated to the endo, endo-tetraene 6 in which all the six aldehyde functionalities are present in a latent form with cis orientation in a locked cyclohexane ring. Although ozonolysis of 6 has so far led only to intractable products, the novelty and brevity of our approach have been demonstrated through the intramolecular acetalizations through ozonolysis in 7 and 15, leading to oxa bowls 9 (seco-hexaoxaperistylane) and 16, respectively. The formation of 9 and 16 requires the generation of five tetrahydrofuran and four oxacyclic rings, respectively, in a single-pot operation.

  DOI：

  10.1021/jo010223n

文献信息

• Electrophilic addition of arylsulfenyl chlorides to tricyclo[4.2.2.02,5]deca-3,7-diene and -3,7,9-triene systems. Novel skeletal rearrangements and serendipitous products
  作者：N. S. Zefirov、A. S. Koz'min、V. N. Kirin、V. V. Zhdankin、Ronald Caple

  DOI：10.1021/jo00339a003

  日期：1981.12
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ag: MVol.B5, 1.3.2.16, page 88 - 90
  作者：

  DOI：——

  日期：——
• Reactions of sulfur halides with unsaturated compounds. 26. Reactions of sulfur dichloride with tricyclo[4.2.2.02,5]deca-3,7-dienes and tricyclo[4.2.2.02,5]deca-3,7,9-trienes. Synthesis of compounds with a novel thiaskeletal structure
  作者：G. A. Tolstikov、B. M. Lerman、T. A. Belogaeva、Yu. T. Struchkov、D. S. Yufit、K. A. Potekhin

  DOI：10.1007/bf00960343

  日期：1990.4
• Avram, M.; Sliam, E.; Nenitzescu, C. D., Liebigs Annalen der Chemie, 1960, vol. 636, p. 184 - 189
  作者：Avram, M.、Sliam, E.、Nenitzescu, C. D.

  DOI：——

  日期：——
• Kazimirchik, I. V.; Lukin, K. A.; Bebikh, G. F., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 8, p. 1540 - 1543
  作者：Kazimirchik, I. V.、Lukin, K. A.、Bebikh, G. F.、Zefirov, N. S.

  DOI：——

  日期：——