tetracyclo[4.4.2.0^2,5.0^7,10]dodeca-3,11-dien-8,9-diol | 42301-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetracyclo[4.4.2.0^2,5.0^7,10]dodeca-3,11-dien-8,9-diol
• 英文别名: (1R,2R,3R,4S,5S,6S,7S,10R)-tetracyclo[4.4.2.02,5.07,10]dodeca-8,11-diene-3,4-diol
• CAS: 42301-40-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: WKECLPYNHMTPBP-SERWXMPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetracyclo[4.4.2.0^2,5.0^7,10]dodeca-3,11-dien-8,9-diol 在 sodium periodate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 tetracyclo[4.4.2.0^2,5.0^7,10]dodeca-3,11-dien-8,9-diol
  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
• 作为产物：
  描述：

  9,10-dimethoxycarbonyltricyclo<4.2.2.0^2,5>deca-3,7-diene 在 sodium tetrahydroborate 、 三甲基氯硅烷 、 sodium 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.5h， 生成 tetracyclo[4.4.2.0^2,5.0^7,10]dodeca-3,11-dien-8,9-diol
  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