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1-(4-methylphenyl)-1,9-dihydro[60]fullerene | 945259-85-8

中文名称
——
中文别名
——
英文名称
1-(4-methylphenyl)-1,9-dihydro[60]fullerene
英文别名
1-(4-methylphenyl)-9-hydro[60]fullerene;1-(4-tolyl)-1,2-dihydro(C60-Ih)[5,6]fullerene;1-phenyl-1,9-dihydro[60]fullerene;9-(4-methylphenyl)-1H-(C60-Ih)[5,6]fullerene
1-(4-methylphenyl)-1,9-dihydro[60]fullerene化学式
CAS
945259-85-8
化学式
C67H8
mdl
——
分子量
812.801
InChiKey
PUXNEATYMVCNTQ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    17.5
  • 重原子数:
    67
  • 可旋转键数:
    1
  • 环数:
    33.0
  • sp3杂化的碳原子比例:
    0.04
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

反应信息

  • 作为反应物:
    描述:
    1-(4-methylphenyl)-1,9-dihydro[60]fullerene乙酰氯 在 aluminum (III) chloride 作用下, 以 邻二氯苯 为溶剂, 反应 0.5h, 以63%的产率得到(E)-1-(2,3-(1,2-dihydro(C60-Ih)[5,6]fullereno)-6-methyl-2,3-dihydro-1H-inden-1-ylidene)propan-2-one
    参考文献:
    名称:
    AlCl3-Catalyzed Tandem Acetylation of Hydroarylated [60]Fullerenes
    摘要:
    The AlCl(3)-catalyzed acetylation of 1,2-hydrophenylated [60]fullerenes, HC(60)-Ar, proceeded via a sequential manner involving the acetylation at the hydrogenated fullerene carbon, the following intramolecular cyclization with the adjacent aryl group, the facile loss of water, and the second acetylation of the generated indenylidene double bond. However, the similar reaction of the hydrobiphenylated analogue brought about the normal acetylation at the terminal aromatic ring prior to the same sequential reactions as did hydrophenylated fullerenes.
    DOI:
    10.1021/ol801239y
  • 作为产物:
    描述:
    4-甲苯硼酸足球烯 在 bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 作用下, 以 邻二氯苯 为溶剂, 反应 12.0h, 以40%的产率得到1-(4-methylphenyl)-1,9-dihydro[60]fullerene
    参考文献:
    名称:
    使用有机硼化合物和铑催化剂选择性地将有机基团引入C60和C70:有机(氢)富勒烯的新合成方法
    摘要:
    描述了C 60和C 70与有机硼化合物的Rh催化反应。这种新的催化方法能够将各种有机基团引入C 60和C 70上。就产率和选择性而言,[Rh(cod)(MeCN)2 ] BF 4被证明是最有效的催化剂。反应通常以高区域选择性和单加成选择性的方式进行。发现水是促进反应的必要添加剂。通过X射线晶体结构分析,我们已经确认了C 70的有机金属基加氢芳基化反应的位点首次。可以合成各种功能性富勒烯,例如富勒烯标记的氨基酸和富勒烯封端的π系统。联苯连接的C 60的X射线晶体结构揭示了利用CH-π相互作用使巴基球组织良好的有趣机会。
    DOI:
    10.1002/asia.201000583
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文献信息

  • Selective Introduction of Organic Groups to C60 and C70 Using Organoboron Compounds and Rhodium Catalyst: A New Synthetic Approach to Organo(hydro)fullerenes
    作者:Masakazu Nambo、Yasutomo Segawa、Atsushi Wakamiya、Kenichiro Itami
    DOI:10.1002/asia.201000583
    日期:2011.2.1
    A Rh‐catalyzed reaction of C60 and C70 with organoboron compounds is described. This new catalytic method enables introduction of various organic groups onto C60 and C70. [Rh(cod)(MeCN)2]BF4 proved to be the most effective catalyst in terms of productivity and selectivity. The reaction generally proceeds with a high regioselectivity and in a mono‐addition selective manner. It was found that water is
    描述了C 60和C 70与有机硼化合物的Rh催化反应。这种新的催化方法能够将各种有机基团引入C 60和C 70上。就产率和选择性而言,[Rh(cod)(MeCN)2 ] BF 4被证明是最有效的催化剂。反应通常以高区域选择性和单加成选择性的方式进行。发现水是促进反应的必要添加剂。通过X射线晶体结构分析,我们已经确认了C 70的有机金属基加氢芳基化反应的位点首次。可以合成各种功能性富勒烯,例如富勒烯标记的氨基酸和富勒烯封端的π系统。联苯连接的C 60的X射线晶体结构揭示了利用CH-π相互作用使巴基球组织良好的有趣机会。
  • A Bench-Stable Pd Catalyst for the Hydroarylation of Fullerene with Boronic Acids
    作者:Susumu Mori、Masakazu Nambo、Liang-Chen Chi、Jean Bouffard、Kenichiro Itami
    DOI:10.1021/ol801936j
    日期:2008.10.16
    A Pd(II) catalyst for the hydroarylation of fullerene with boronic acids is presented. Treatment of C-60 with an arylboronic acid in the presence of a catalytic amount of Pd(2-PyCH=NPh)(OCOC6F5)(2) in H2O/1,2-Cl2C6H4 at room temperature furnishes the hydroarylation product (Ar-C-60-H) in good yield with high selectivity. This complex possesses high catalytic activity paired with bench stability in the solid state.
  • Rh-Catalyzed Arylation and Alkenylation of C<sub>60</sub> Using Organoboron Compounds
    作者:Masakazu Nambo、Ryoji Noyori、Kenichiro Itami
    DOI:10.1021/ja073042x
    日期:2007.7.1
    A new organoboron-based arylation and alkenylation of C-60 catalyzed by a rhodium complex was developed. A treatment of C-60 with an organoboron compound in the presence of a catalytic amount of [Rh(cod)(CH3CN)(2)]BF4 in H2O/1,2-Cl2C6H4 furnished a functionalized fullerene (R-C-60-H) with good to excellent selectivity. Aryl, heteroaryl, and alkenyl groups can be installed by the reactions using the corresponding boronic acids, pinacol esters, and potassium trifluoroborates.
  • AlCl<sub>3</sub>-Catalyzed Tandem Acetylation of Hydroarylated [60]Fullerenes
    作者:Ken Kokubo、Shinya Tochika、Mai Kato、Yui Sol、Takumi Oshima
    DOI:10.1021/ol801239y
    日期:2008.8.7
    The AlCl(3)-catalyzed acetylation of 1,2-hydrophenylated [60]fullerenes, HC(60)-Ar, proceeded via a sequential manner involving the acetylation at the hydrogenated fullerene carbon, the following intramolecular cyclization with the adjacent aryl group, the facile loss of water, and the second acetylation of the generated indenylidene double bond. However, the similar reaction of the hydrobiphenylated analogue brought about the normal acetylation at the terminal aromatic ring prior to the same sequential reactions as did hydrophenylated fullerenes.
  • Playing with Protic Additives to Improve the Outcome of Rhodium‐Catalyzed Hydroarylation of Fullerene C<sub>60</sub> with Arylboronic Acids
    作者:Merve Ergun Dönmez、Måns Eriksson、Gustav Hulu、Michael Nordström、Helena Grennberg
    DOI:10.1002/hlca.202300206
    日期:2024.2
    Abstract

    A new one‐phase process for hydroarylation of C60 fullerene using arylboronic acids and a rhodium catalyst in an aromatic solvent containing soluble protic additives is described. Yields of monohydroarylated product with tert‐butanol and water as the protic additive range from 14 to 50 % depending on which arylboronic acid is used after reaction times of 4 hours or less which is a significant improvement from the outcome of reactions carried out using conditions from the literature. Accurate monitoring of reaction outcomes was achieved by a combination of UV‐Vis spectroscopy and 1H‐NMR spectroscopy: C60 conversion was determined using an analytical HPLC‐UV‐vis method employing commonly available columns for the separation, while product formation was quantified by 1H‐NMR spectroscopy with an internal standard. Moreover, two new arylboronic acids carrying 4‐alkynyl aryl substituents, synthesized using Sonogashira couplings, are reported, as well as the use of these in the hydroarylation of C60.

    摘要 描述了一种在含有可溶性原生添加剂的芳香溶剂中使用芳基硼酸和铑催化剂进行 C60 富勒烯加氢反应的单相新工艺。使用叔丁醇和水作为原生添加剂,在反应时间为 4 小时或更短的情况下,根据所使用的芳基硼酸的不同,单氢芳基化产物的产率为 14% 至 50%,这比使用文献条件进行的反应结果有了显著改善。反应结果的精确监测是通过紫外可见光谱和 1H-NMR 光谱相结合来实现的:采用 HPLC-UV-vis 分析方法,使用常见的分离柱测定 C60 的转化率,同时使用内标 1H-NMR 光谱定量分析产物的形成。此外,还报道了利用 Sonogashira 偶联合成的两种携带 4- 烷基芳基取代基的新型芳基硼酸,以及在 C60 的加氢反应中使用这些芳基硼酸的情况。
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