1,16-C60[CMe(CO2Et)2]2 | 1228661-07-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,16-C60[CMe(CO2Et)2]2
• 英文别名: 1,16-bis(1',1'-di(carboethoxy)ethyl)-1,16-dihydro[60,Ih]fullerene
• CAS: 1228661-07-1
• 化学式: C₇₆H₂₆O₈
• 分子量: 1067.04
• InChiKey: JVAWGPYTAPGKIO-KAUZTFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  84.0
• 可旋转键数：
  10.0
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-溴-2-甲基丙二酸二乙酯 、 1,16-C60[CMe(CO2Et)2]2 在 萘 、 1,4-C60[CMe(CO2Et)2]2 、 sodium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以17%的产率得到1,16,29,38,43,60-C60[CMe(CO2Et)2]6
  参考文献：
  名称：

  Synthesis and Regiochemistry of [60]Fullerenyl 2-Methylmalonate Bisadducts and their Facile Electron-Accepting Properties

  摘要：

  A simple one-pot reaction using in situ chemically generated Na-naphthalenide as an electron reductant in the preferential generation of C-60(2-) is described. Trapping of C-60(2-) intermediate with 2 molar equiv of sterically hindered 2-bromo-2-methylmalonate ester afforded two singly bonded fullerenyl bis-adducts C-60[-CMe(CO2Et)(2)](2) in 35% and 7% yield, respectively. The regiochemistry of these two products was determined to be 1,4- and 1,16-bisadducts, respectively, by NMR, LCMS, and X-ray single crystal structural analysis. The minor 1,16-bisadduct 2 exhibits long wavelength absorption bands in the near-IR region and prominent electron-accepting characteristics as compared with those of the major 1,4-bisadduct and pristine C-60. As revealed by DFT calculation, we propose that the origin of these unusual characters of 2 arises from the moiety of [18 pi]-trannulene, in close resemblance to that oldie highly symmetrical emerald green 1,16,29,38,43,60-hexaadduct of C-60, EF-6MC(n). Accordingly, we anticipate a fast progressive formation of plausible 1,16-bisadduct-like intermediate moieties on a C-60 cage as the precursor structure leading to the formation of EF-6MC(n), by taking the corresponding regiochemistry and electronic properties into account.

  DOI：

  10.1021/jo1007674
• 作为产物：
  描述：

  2-溴-2-甲基丙二酸二乙酯 、 足球烯 在 萘 、 sodium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以35%的产率得到1,4-C60[CMe(CO2Et)2]2
  参考文献：
  名称：

  Synthesis and Regiochemistry of [60]Fullerenyl 2-Methylmalonate Bisadducts and their Facile Electron-Accepting Properties

  摘要：

  A simple one-pot reaction using in situ chemically generated Na-naphthalenide as an electron reductant in the preferential generation of C-60(2-) is described. Trapping of C-60(2-) intermediate with 2 molar equiv of sterically hindered 2-bromo-2-methylmalonate ester afforded two singly bonded fullerenyl bis-adducts C-60[-CMe(CO2Et)(2)](2) in 35% and 7% yield, respectively. The regiochemistry of these two products was determined to be 1,4- and 1,16-bisadducts, respectively, by NMR, LCMS, and X-ray single crystal structural analysis. The minor 1,16-bisadduct 2 exhibits long wavelength absorption bands in the near-IR region and prominent electron-accepting characteristics as compared with those of the major 1,4-bisadduct and pristine C-60. As revealed by DFT calculation, we propose that the origin of these unusual characters of 2 arises from the moiety of [18 pi]-trannulene, in close resemblance to that oldie highly symmetrical emerald green 1,16,29,38,43,60-hexaadduct of C-60, EF-6MC(n). Accordingly, we anticipate a fast progressive formation of plausible 1,16-bisadduct-like intermediate moieties on a C-60 cage as the precursor structure leading to the formation of EF-6MC(n), by taking the corresponding regiochemistry and electronic properties into account.

  DOI：

  10.1021/jo1007674

文献信息

• Synthesizing 1,23-C₆₀ Adducts with Improved Efficiency: A Type of Stable and Highly Soluble C₆₀ Derivatives
  作者：Dan Li、Zong-Jun Li、Fa-Gui He、Chao Geng、Xiang Gao

  DOI：10.1021/acs.joc.9b02272

  日期：2019.11.15

  and 1,7-C60 adducts, the 1,23-C60 adducts are an important type of C60 derivatives, where the property of the fullerene compounds is significantly affected by the addition pattern. However, much less is known on the adducts due to the less availability of the compounds. Herein, the hydroxide-promoted reactions of C60 with 2-alkylmalonates are reported, which produce the 1,23-C60 adducts with improved

  除了1,9-和1,7-C60加合物外，1,2-C60加合物是一种重要的C60衍生物类型，其中富勒烯化合物的性质受加成方式的影响很大。但是，由于化合物的可利用性较低，因此对加合物的了解很少。在此，报道了C60与2-烷基丙二酸酯的氢氧化物促进的反应，其以提高的效率产生1,23-C60加合物。为了对反应机理进行探究，对反应进行了原位可见-近红外光谱测量。相对于1，7-异构体，获得的1，23-C60加合物表现出良好的热稳定性和较好的溶解性。
• Synthesis of Disubstituted [60]Fullerene-Fused Lactones: Ferric Perchlorate-Promoted Reaction of [60]Fullerene with Malonate Esters
  作者：Fa-Bao Li、Xun You、Guan-Wu Wang

  DOI：10.1021/ol102056k

  日期：2010.11.5

  The ferric perchlorate-mediated reaction of [60]fullerene with substituted malonate esters in the presence of acetic anhydride afforded the rare disubstituted [60]fullerene-fused lactones. A possible reaction mechanism is proposed.