(1R,2R,4S,5S)-Tricyclo[3.2.1.0^2,4]octane-2,4-dicarboxylic acid | 143668-25-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S,5S)-Tricyclo[3.2.1.0^2,4]octane-2,4-dicarboxylic acid
• 英文别名: (1S,2S,4R,5R)-tricyclo[3.2.1.02,4]octane-2,4-dicarboxylic acid
• CAS: 143668-25-1
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: SZTZKBYJOWCDPB-XCVPVQRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,5S)-Tricyclo[3.2.1.0^2,4]octane-2,4-dicarboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (1R,2R,4S,5S)-Tricyclo[3.2.1.0^2,4]octane-2,4-dicarbonyl dichloride
  参考文献：
  名称：

  Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene

  摘要：

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.

  DOI：

  10.1021/jo00048a032
• 作为产物：
  描述：

  (1R,2S,3R,4S)-2-Chloromethyl-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid diethyl ester 在 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 80.0h， 生成 (1R,2R,4S,5S)-Tricyclo[3.2.1.0^2,4]octane-2,4-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene

  摘要：

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.

  DOI：

  10.1021/jo00048a032

文献信息

• Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene
  作者：Philip J. Chenier、Michael J. Bauer、Christina L. Hodge

  DOI：10.1021/jo00048a032

  日期：1992.10

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.