1-[(1R,2S,3R,4S)-3-pentanoyl-2-bicyclo[2.2.1]hept-5-enyl]pentan-1-one | 194983-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1R,2S,3R,4S)-3-pentanoyl-2-bicyclo[2.2.1]hept-5-enyl]pentan-1-one
• CAS: 194983-64-7
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: MPTZAEVBAZIRIL-GANFFNEQSA-N

物化性质

• 沸点：
  373.7±42.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  1-[(1R,2S,3R,4S)-3-pentanoyl-2-bicyclo[2.2.1]hept-5-enyl]pentan-1-one 在 水 、 碘 、 potassium hydride 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1,10-Dibutyl-9,11,12-trioxapentacyclo[5.4.1.02,6.03,10.04,8]dodecane
  参考文献：
  名称：

  Synthesis of Diacetal Trioxa-Cage Compounds via a Sequential Cyclization Reaction of Norbornene Derivatives Induced by Electrophiles

  摘要：

  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.

  DOI：

  10.1021/jo970348l
• 作为产物：
  描述：

  2,5-dibutylfuran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(1R,2S,3R,4S)-3-pentanoyl-2-bicyclo[2.2.1]hept-5-enyl]pentan-1-one
  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

• Synthesis of Diacetal Trioxa-cage Compounds via Reaction of Bicyclo[2.2.1]heptenes and Bicyclo[2.2.2]octenes with Dimethyldioxirane
  作者：Hui-Chang Lin、Hsien-Jen Wu

  DOI：10.1016/s0040-4020(99)00997-7

  日期：2000.1

  A new entry for the synthesis of diacetal trioxa-cage compounds via oxirane-induced sequential cyclization reaction of 2,3-bis-endo-diacylbicyclo[2.2.1]-5-heptenes and 2,3-bis-endo-diacylbicyclo[2.2.2]-5-octenes is reported. In the case of bicyclo[2.2.2]octenes, sequential cyclization reaction induced by iodine as electrophile failed. We have also demonstrated that dimethyldioxirane can selectively

  通过环氧乙烷诱导的2,3-双-内-二酰基双环[2.2.1] -5-庚烯和2,3-双-内-二酰基双环[2.2 ]的环氧乙烷顺序环化反应合成二缩醛三氧杂笼化合物的新方法.2] -5-辛烯的报道。在双环[2.2.2]辛烯的情况下，碘作为亲电试剂引起的顺序环化反应失败。我们还证明了二甲基二环氧乙烷可以选择性地氧化半缩醛以产生具有完整仲羟基的内酯。
• 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。
• Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane
  作者：Hui-Chang Lin、Chung-Yi Wu、Hsien-Jen Wu

  DOI：10.1002/jccs.199700094

  日期：1997.12

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.