2endo.3endo-dibenzoyl-norbornene-(5) | 74007-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2endo.3endo-dibenzoyl-norbornene-(5)
• 英文别名: 2endo.3endo-Dibenzoyl-norbornen-(5)；[(1R,2S,3R,4S)-3-benzoyl-2-bicyclo[2.2.1]hept-5-enyl]-phenylmethanone
• CAS: 74007-33-3
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: KAFIRIBTVAQVNC-QGFMHUBQSA-N

物化性质

• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2endo.3endo-dibenzoyl-norbornene-(5) 在 palladium on activated charcoal 氢气 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以97%的产率得到2-endo-3-endo-Dibenzoylbicyclo<2.2.1>heptane
  参考文献：
  名称：

  1-Thia-Cope Rearrangements during the Thionation of 2-endo-3-endo-Bis(aroyl)bicyclo[2.2.1]hept-5-enes

  摘要：

  DOI：

  10.1021/jo00092a034
• 作为产物：
  描述：

  (Z)-1,4-二苯基-2-丁烯-1,4-二酮 、 环戊二烯 生成 2endo.3endo-dibenzoyl-norbornene-(5)
  参考文献：
  名称：

  的双-臭氧分解内切在二氯甲烷-甲醇-diacylbicyclo [2.2.1]庚烯

  摘要：

  的双-臭氧分解内-diacylbicyclo [2.2.1]庚烯3A - d在-78℃下在二氯甲烷-甲醇，得到的氢过氧化物6A - d在70-80％的产率。的臭氧分解双-内切-diacetylbicyclo [2.2.2]辛烯15和双-内切二乙酰基-7-氧杂二环[2.2.1]庚烯16相同的反应条件下，得到氢过氧化物17和18， 分别。首次观察到羰基的分子内顺序亲核加成，并且发现其比将甲醇分子的分子间亲核加成更快。在-78°C下于CH 2 Cl 2 -MeOH中进行化合物23的臭氧分解，然后用Me 2 S还原，得到化合物24和25，其中甲氧基的立体化学通过X射线分析确定。

  DOI：

  10.1016/j.tet.2011.07.055

文献信息

• A noval iodine-induced sequential cyclization reaction of norbornene derivatives leading to the formation of novel iodo-cage compounds
  作者：Hsien-Jen Wu、Shih-Hwa Tsai、Wen-Sheng Chung

  DOI：10.1039/cc9960000375

  日期：——

  Teatment of the bis-endo-thioester and acyl group substituted norbornenes 1a–d and 9a–c with iodine in aqueous tetrahydrofuran at 25 °C gave the noval iodo-cage compounds 2a–d and 10a–c in 80–90% yields respectively, the first example of sequential cyclization of norbornene derivatives induced by an iodine electrophile.

  在 25 °C 的四氢呋喃水溶液中，用碘处理双内硫酯和酰基取代的降冰片烯 1a-d 和 9a-c，分别得到新的碘笼化合物 2a-d 和 10a-c，产率分别为 80-90% ，第一个由碘亲电子试剂诱导的降冰片烯衍生物连续环化的例子。
• The Synthesis of 1,3-Diphenyldihydroisobenzofurans, 1,3-Diphenylisobenzofurans and o-Dibenzoylbenzenes from the Diene Addition Products to Dibenzoylethylene
  作者：Roger Adams、Marvin H. Gold

  DOI：10.1021/ja01858a012

  日期：1940.1
• Novel Oxa-Cage Compounds: Synthesis, Structures, and the Formation Mechanism of Tetraacetal Oxa-Cages and Convex Tetraquinane Oxa-Cages
  作者：Hsien-Jen Wu、Chu-Chung Lin

  DOI：10.1021/jo00128a031

  日期：1995.11

  Several novel tetraacetal era-cage compounds 5a-d and convex tetraquinane era-cage compounds 16a-d and 17b-d are synthesized from alkylfurans in three steps. Ozonolysis of the cis-endo-1,4-diones 3a-d in dichloromethane at -78 degrees C followed by reduction with dimethyl sulfide gives the era-cages 5a-d in high yields, respectively. The structures of these new tetraacetal era-cages are deduced from their spectral data and proven for the first time by X-ray analysis of the crystalline compound 5a. Ozonolysis of 3a-d in dichloromethane at -78 degrees C followed by treatment with triethylamine gives the convex tetraquinane era-cages 16a-d and 17b-d in 85-90% yields, respectively. The structures of these novel convex tetraquinane era-cages are finally proven by X-ray analysis of the crystalline compound 16a. Two reaction mechanisms via the common final ozonides are proposed for the formation of these two different types of era-cage compounds. The structures of the final ozonides formed by ozonolysis of the norbornene derivatives 3 are deduced to be 9 with endo stereochemistry on the basis of their spectral data and the formation of these two types of era-cages from the final ozonides. In reaction with the final ozonides, triethylamine is found to act as a base instead of a reducing agent, a different function from that of dimethyl sulfide. The synthesis of era-cages 24 and 25, which possess aromatic substituents directly on the skeleton, has also been accomplished.
• Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group
  作者：Hsien-Jen Wu、Ching-Shiun Chao、Chu-Chung Lin

  DOI：10.1021/jo980632s

  日期：1998.10.1

  The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2Cl2 at -78 degrees C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.
• Synthesis of Diacetal Trioxa-Cage Compounds via a Sequential Cyclization Reaction of Norbornene Derivatives Induced by Electrophiles
  作者：Hsien-Jen Wu、Shih-Hwa Tsai、Jyh-Haur Chern、Hui-Chang Lin

  DOI：10.1021/jo970348l

  日期：1997.9.1

  The synthesis of diacetal trioxa-cage compounds via a sequential cyclization reaction of norbornene derivatives induced by electrophiles in a short sequence is reported. Treatment of the norbornene derivatives 2a-d and 10b with I-2 in aqueous THF in the presence of KI at 25 degrees C regioselectively gave the iodo-cage compounds 3a-d and 11 in 80-90% yields, respectively, via a iodine-induced sequential cyclization reaction. No detectable amount of other regioisomers or monocyclization products was obtained. The synthesis of triora-cages 14a-e was accomplished from 3a-d and 11 in a two-step sequence. Treatment of diacylnorbornenes 15a-f with I-2 in aqueous THF at 25 degrees C regioselectively and stereoselectively gave the sequential cyclization products 16a-f, respectively, which were converted in one step to the diacetal trioxa-cages 24a-f in high yields. The structure of these trioxa-cages was proven by X-ray analysis of the crystalline compound 14e. Other electrophiles, such as bromine, m-CPBA, and Hg(OAc)(2), were also found to be effective for the sequential cyclization reaction. Oxymercuration of 15a-f and 2a-c with Hg(OAc)(2) in aqueous THF followed by reduction with NaBH4 at 25 degrees C gave compounds 28a-f and 30b,d,c in high yields, respectively.