2-carbomethoxy-9-oxapentacyclo<4.4.0.0^2,5.0^3,10.0^4,7>decan-8-one | 125848-33-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-carbomethoxy-9-oxapentacyclo<4.4.0.0^2,5.0^3,10.0^4,7>decan-8-one
• 英文别名: methyl 10-oxa-9-oxopentacyclo<4.4.0.0^2,5.0^3,8.0^4,7>decane-4-carboxylate；4-methoxycarbonyl-9-oxapentacyclo<4.4.0.0^2,5.0^3,8.0^4,7>decan-10-one；methyl 10-oxo-9-oxapentacyclo[4.4.0.02,5.03,8.04,7]decane-4-carboxylate
• CAS: 125848-33-1
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: UTKJIKFSWAGKKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-Bromotetracyclo[4.2.0.02,5.03,8]octane-1,4-dicarboxylic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-carbomethoxy-9-oxapentacyclo<4.4.0.0^2,5.0^3,10.0^4,7>decan-8-one
  参考文献：
  名称：

  Hydrogen bromide cleavage of cubane-1,4-dicarboxylic acid. Easy entry into the nortwistbrendane(ene) system

  摘要：

  DOI：

  10.1021/jo00296a048

文献信息

• Base-Promoted Rearrangement of 1,5-Dibromopentacyclo[5.3.0.0^2,5.0^3,9.0^4,8]decane-6,10-dione: Easy Entry of a Novel Cage System, 10-Oxa-9-oxopentacyclo[5.3.0.0^2,4.0^3,6.0^5,8]decane
  作者：Tomohiro Nigo、Takeshi Hasegawa、Yoshiyuki Kuwatani、Ikuo Ueda

  DOI：10.1246/bcsj.66.2068

  日期：1993.7

  product 7. Deacetalization was accomplished by treating with concentrated sulfuric acid to give 1,5-dibromopentacyclo[5.3.0.02,5.03,9.04,8]decane-6,10-dione (9). Compound 9 was converted into a new cage system, 10-oxa-9-oxopentacyclo[5.3.0.02,4.03,6.05,8]decane, in a high yield by treating with 5% aqueous potassium hydroxide at 80 °C.

  2-溴-2,4-环戊二烯酮乙缩醛 (2) 的狄尔斯-阿尔德二聚反应得到内-2,7-二溴二环戊二烯-1,8-二酮 1,8-双 (乙缩醛) (3) 作为次要产物产率为 4.5%。紫外线照射 5 产生二聚产物 7。通过用浓硫酸处理来完成脱缩醛反应，得到 1,5-二溴五环 [5.3.0.02,5.03,9.04,8]癸烷-6,10-二酮 (9)。通过在 80 °C 下用 5% 氢氧化钾水溶液处理，将化合物 9 转化为新的笼系统，即 10-oxa-9-oxopentacyclo[5.3.0.02,4.03,6.05,8]decane。
• Mechanistic Study of Base-Promoted Rearrangement of 1,5-Dibromopentacyclo[5.3.0.0^2,5.0^3,9.0^4,8]decane-6,10-dione to 10-Oxa-9-oxopentacyclo[5.3.0.0^2,4.0^3,6.0^5,8]decane-3-carboxylic Acid
  作者：Takeshi Hasegawa、Tomohiro Nigo、Yoshiyuki Kuwatani、Ikuo Ueda

  DOI：10.1246/bcsj.66.2676

  日期：1993.9

  The conversion of 1,5-dibromopentacyclo[5.3.0.02,5.03,9.04,8]decane-6,10-dione (1) to 10-oxa-9-oxopentacyclo [5.3.0.02,4.03,6.05,8]decane-3-carboxylic acid (6) on treatment with 5% aqueous potassium hydroxide was shown to proceed through 1, exo-7-dibromo-9-oxotetracyclo[4.3.0.02,5.03,8]nonane-endo-4-carboxylic acid (2). Treatment of 1 with the base in heavy water gave rise to 2-d-6 deuterated at the 2-position, but 2 gave the protium analog 6 after the same treatment. These results are discussed in relation to reactions of similar compounds which have been previously described in the literature.

  1,5-二溴五环[5.3.0.02,5.03,9.04,8]癸烷-6,10-二酮（1）经 5%氢氧化钾水溶液处理后转化为 10-氧杂-9-氧代五环[5.3.0.02,4.03,6.5%氢氧化钾水溶液处理 10-氧杂-9-氧代五环[5.3.0.02,4.03,6.在重水中用碱处理 1，可得到在 2 位氚化的 2-d-6，但同样处理 2 后可得到氕类似物 6。这些结果与以前文献中描述的类似化合物的反应进行了讨论。
• EATON, PHILIP E.;MILLIKAN, RANDALL;ENGEL, PETER, J. ORG. CHEM., 55,(1990) N, C. 2823-2826
  作者：EATON, PHILIP E.、MILLIKAN, RANDALL、ENGEL, PETER

  DOI：——

  日期：——