(Z)-3-Nonene-2,5-dione | 90467-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-Nonene-2,5-dione
• 英文别名: 3Z-Nonen-2,5-dione；(Z)-non-3-ene-2,5-dione
• CAS: 90467-65-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: JVDFOBAEQVATET-SREVYHEPSA-N

物化性质

• 沸点：
  260.2±23.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (Z)-3-Nonene-2,5-dione 在 二甲基硫 、 臭氧 、 对苯二酚 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  Lin, Chu-Chung; Wu, Hsien-Jen, Journal of the Chinese Chemical Society, 1995, vol. 42, # 5, p. 815 - 820

  摘要：

  DOI：
• 作为产物：
  描述：

  2-丁基-5-甲基呋喃 在 阻聚剂701 、 350 U laccase 作用下， 以 正辛烷 为溶剂， 以33%的产率得到(Z)-3-Nonene-2,5-dione
  参考文献：
  名称：

  漆酶催化的2，5-二烷基呋喃的立体选择性氧化环开环，使用空气作为氧化剂成2-ene-1,4-二酮

  摘要：

  漆酶催化的开环 2,5-二甲基呋喃使用空气作为氧化剂立体选择产生（Z）-或（E）-3-己烯-2,5-二酮取决于所使用的介体：与TEMPO一起形成（Z）-3-己烯-2,5-二酮，而TEMPO和紫草酸 给 （E）-3-己烯-2,5-二酮。（Z）-选择性环裂解扩展到各种对称和不对称的2，5-二烷基呋喃。

  DOI：

  10.1039/c1gc15810d

文献信息

• Stereoselective Synthesis of <i>cis</i>-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO₃
  作者：Liqun Yang、Jingyang Wang、Yue Wang、Xiaotong Li、Wei Liu、Zhaoguo Zhang、Xiaomin Xie

  DOI：10.1021/acs.joc.1c00613

  日期：2021.11.5

  We report a highly efficient and selective catalytic system, ABNO (9-azabicyclo-[3.3.1]nonane N-oxyl)/HNO3, for the aerobic oxidation of substituted furans to cis-2-ene-1,4-diones under mild reaction conditions using oxygen as the oxidant. The catalyst system is amenable to various substituted (mon-, di-, and tri-) furans and tolerates diverse functional groups, including cyano, nitro, naphthyl, ketone

  我们报告了一种高效和选择性催化体系 ABNO (9-azabicyclo-[3.3.1] nonane N -oxyl)/HNO 3，用于将取代的呋喃有氧氧化为顺式-2-ene-1,4-二酮以氧气为氧化剂，反应条件温和。该催化剂体系适用于各种取代的（单-、二-和三-）呋喃，并耐受多种官能团，包括氰基、硝基、萘基、酮、酯、杂环，甚至甲酰基。基于对照和18个O标记实验，提出了氧化的可能机理。
• Synthesis of Tetraacetal Pentaoxa-Cages and Convex Oxa-Cages by Ozonolysis of 7-Oxabicyclo[2.2.1]heptenes
  作者：Chu-Chung Lin、Hsien-Jen Wu

  DOI：10.1055/s-1996-4291

  日期：1996.6

  Tetraacetal pentaoxa-cage compounds 4a and 4b and convex oxa-cage compounds 6, 7 and 8 are synthesized from alkylfurans in three steps. Ozonolysis of the endo adducts 2a and 2b in dichloromethane at -78°C followed by reduction with dimethyl sulfide gave the tetraacetal pentaoxa-cages 4a and 4b in 85-90% yields, respectively. Ozonolysis of 2a and 2b in dichloromethane at -78°C followed by treatment with triethylamine gave the convex oxa-cages 6, 7 and 8 in 85-90% yields, respectively. The synthesis of the tetraacetal pentaoxa-cage 12, possessing aromatic substituents directly on the skeleton of the oxa-cages, has also been accomplished.

  四缩醛五氧杂笼化合物 4a 和 4b 以及凸形氧杂笼化合物 6、7 和 8 是由烷基呋喃分三步合成的。在 -78°C 下，在二氯甲烷中对内加合物 2a 和 2b 进行臭氧分解，然后用二甲基硫醚还原，得到四缩醛五氧杂笼化合物 4a 和 4b，产率分别为 85%-90% 。2a 和 2b 在-78°C 的二氯甲烷中进行臭氧分解，然后用三乙胺处理，分别得到了凸面氧杂笼 6、7 和 8，收率为 85-90%。此外，还合成了四缩醛五氧杂笼 12，它的芳香取代基直接位于氧杂笼的骨架上。
• 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.