| 1152414-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1152414-23-7
• 化学式: C₆₉H₈O₄
• 分子量: 900.82
• InChiKey: VJIJNOBFSALWFY-UHFFFAOYSA-N

物化性质

• 密度：
  2.85±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  73
• 可旋转键数：
  2
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  在 四丁基高氯酸铵 、 溶剂黄146 作用下， 以 邻二氯苯 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  逆转的Baeyer-Villiger反应：将[60]富勒烯融合的内酯电化学还原为[60]富勒烯融合的酮†

  摘要：

  首次实现了从[60]富勒烯融合的内酯到[60]富勒烯融合的酮的高效电化学还原，这是逆Baeyer-Villiger反应的正式过程。在乙酸存在下，电化学生成的双阴离子[60]富勒烯稠合的内酯可以转化为[60]富勒烯稠合的酮，产率为85-91％。已经进行了对照实验以阐明反应机理。产品已通过光谱数据和单晶X射线分析进行了表征。此外，还已经研究了电化学性质。

  DOI：

  10.1039/c8sc05089a
• 作为产物：
  描述：

  足球烯 、 2-氨基-4,5-二甲氧基苯甲酸 在 三乙胺 、 亚硝酸异戊酯 作用下， 以 氯苯 为溶剂， 反应 1.5h， 以37%的产率得到
  参考文献：
  名称：

  A facile access to [60]fullerene-fused δ-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases

  摘要：

  在三乙胺存在下，[60]富勒烯与蒽酸和亚硝酸异戊酯反应，意外地得到了[60]富勒烯融合的δ-内酯，而用其他已知方法很难制备这种物质；有机碱在不寻常的反应途径中发挥了关键作用。

  DOI：

  10.1039/b820395d

文献信息

• A facile access to [60]fullerene-fused δ-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases
  作者：Guan-Wu Wang、Bo Zhu

  DOI：10.1039/b820395d

  日期：——

  The reaction of [60]fullerene with anthranilic acids and isoamyl nitrite in the presence of triethylamine unexpectedly afforded [60]fullerene-fused δ-lactones, which would be difficult to be prepared by other known methods; the organic base played a crucial role in the unusual reaction pathway.

  在三乙胺存在下，[60]富勒烯与蒽酸和亚硝酸异戊酯反应，意外地得到了[60]富勒烯融合的δ-内酯，而用其他已知方法很难制备这种物质；有机碱在不寻常的反应途径中发挥了关键作用。
• A retro Baeyer–Villiger reaction: electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones
  作者：Chuang Niu、Dian-Bing Zhou、Yong Yang、Zheng-Chun Yin、Guan-Wu Wang

  DOI：10.1039/c8sc05089a

  日期：——

  A highly efficient electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones, a formal process of retro Baeyer–Villiger reaction, has been achieved for the first time. The electrochemically generated dianionic [60]fullerene-fused lactones can be transformed into [60]fullerene-fused ketones in the presence of acetic acid in 85–91% yields. Control experiments have been

  首次实现了从[60]富勒烯融合的内酯到[60]富勒烯融合的酮的高效电化学还原，这是逆Baeyer-Villiger反应的正式过程。在乙酸存在下，电化学生成的双阴离子[60]富勒烯稠合的内酯可以转化为[60]富勒烯稠合的酮，产率为85-91％。已经进行了对照实验以阐明反应机理。产品已通过光谱数据和单晶X射线分析进行了表征。此外，还已经研究了电化学性质。
• Electrosynthesis of Decorated Basket Molecules: [60]Fullerene-Fused 12-Membered Macrolactones
  作者：Chuang Niu、Zhiwei Xu、Xinmin Huang、Wei-Feng Wang、Zheng-Chun Yin、Guan-Wu Wang

  DOI：10.1021/acs.orglett.2c01948

  日期：2022.8.5

  12-membered macrolactones, has been achieved efficiently for the first time by the electrochemical reduction of [60]fullerene-fused 6-membered lactones and subsequent ring expansion with 1,2-bis(1-bromoalkyl)benzenes. The observed isomeric distributions of the obtained macrolactones are elucidated by theoretical calculations. The product structures have been firmly established by single-crystal X-ray analyses

  通过电化学还原 [60] 富勒烯稠合 6 元内酯并随后用 1 ,2-双(1-溴烷基)苯。通过理论计算阐明了所观察到的大环内酯的异构分布。产品结构已通过单晶 X 射线分析确定。
• Direct benzyne-C60 addition does not generate a [5,6] open fulleroid
  作者：Ryo Mizunuma、Teruhiko Tanaka、Yoshihiro Nakamura、Yuki Kamijima、Yoshio Kabe

  DOI：10.1016/j.tet.2017.12.023

  日期：2018.2

  Recent reports describe the different products resulting from the reaction of C-60 with benzyne generated from anthranilic acid derivatives and isoamyl nitrate in the presence and absence of triethylamine. Reinvestigation here via H-1, C-13, HMBC NMR and Mass spectroscopy elucidates that these products are the [6,6] closed C-60-fused delta lactones, and not the [5,6] open fulleroids which would result from benzyne addition. Furthermore, theoretical calculations show that the open isomer [5,6] benzyne addition is less stable than the [5,6] closed isomer as an isolable product. (C) 2017 Elsevier Ltd. All rights reserved.
• Retro Baeyer–Villiger reaction: thermal conversion of the [60]fullerene-fused lactones to ketones
  作者：Chuang Niu、Zheng-Chun Yin、Wei-Feng Wang、Xinmin Huang、Dian-Bing Zhou、Guan-Wu Wang

  DOI：10.1039/d2cc00126h

  日期：——

  The conversion of the [60]fullerene-fused lactones to ketones with triflic anhydride as an unusual reductant under aerobic conditions has been achieved in excellent yields. The present thermal retro Baeyer–Villiger reaction from lactones to ketones has no precedents. In addition, the unique ring-opened peroxy [60]fullerene derivatives can be obtained by the electrochemical reactions of the synthesized

  在有氧条件下，以三氟甲磺酸酐作为一种不寻常的还原剂，将 [60] 富勒烯稠合内酯转化为酮类的转化率很高。目前从内酯到酮的热逆 Baeyer-Villiger 反应没有先例。此外，通过合成的[60]富勒烯稠酮的电化学反应，可以获得独特的开环过氧[60]富勒烯衍生物。