1-(dimethylphenylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene | 156551-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-(dimethylphenylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene
• 英文别名: 9H-(C60-Ih)[5,6]fulleren-1-ylmethyl-dimethyl-phenylsilane
• CAS: 156551-17-6
• 化学式: C₆₉H₁₄Si
• 分子量: 870.956
• InChiKey: MSQXXPHVLJQBOZ-UHFFFAOYSA-N

物化性质

• 密度：
  2.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.76
• 重原子数：
  70
• 可旋转键数：
  3
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.07
• 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-(dimethylphenylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene 、 1,1-二乙氧基-2-碘乙烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 苯甲腈 为溶剂， 反应 15.17h， 以73%的产率得到1-diethoxyethyl-7-dimethylphenylsilylmethyl-1,7-dihydro(C60-I_h)[5,6]fullerene
  参考文献：
  名称：

  Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction

  摘要：

  Monoaddition of Grignard reagents, in particular tri(organo)silylmethyl magnesium chlorides, to [60]fullerene took place smoothly in the presence of dimethylformamideto produce (organo)(hydro)[60]fullerenes, (C60RH)-H-1, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R-, which was then alkylated to obtain 58 pi-electron di(organo)[60]fullerenes, (C60RR2)-R-1, in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo)[60] fullerenes bearing the same or different organic addends on the [60] fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.

  DOI：

  10.1021/ja8041299
• 作为产物：
  描述：

  magnesium,methanidyl-dimethyl-phenylsilane,chloride 、 足球烯 在 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 邻二氯苯 为溶剂， 以82%的产率得到1-(dimethylphenylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene
  参考文献：
  名称：

  Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction

  摘要：

  Monoaddition of Grignard reagents, in particular tri(organo)silylmethyl magnesium chlorides, to [60]fullerene took place smoothly in the presence of dimethylformamideto produce (organo)(hydro)[60]fullerenes, (C60RH)-H-1, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R-, which was then alkylated to obtain 58 pi-electron di(organo)[60]fullerenes, (C60RR2)-R-1, in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo)[60] fullerenes bearing the same or different organic addends on the [60] fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.

  DOI：

  10.1021/ja8041299

文献信息

• Regiocontrolled Synthesis of 1,2-Di(organo)fullerenes via Copper-Assisted 1,4-Aryl Migration from Silicon to Carbon
  作者：Ying Zhang、Yutaka Matsuo、Eiichi Nakamura

  DOI：10.1021/ol202511u

  日期：2011.11.18

  developed. It was demonstrated that the cationic fullerene is useful for functionalization of fullerene, in particular, for the synthesis of noncyclic 1,2-di(organo)[60]fullerene derivatives that can be selectively prepared through intramolecular 1,4-aryl migration of an aryl group from a silicon atom to the fullerene core.

  已经开发出一种简洁有效的方法，该方法通过用铜（II）盐氧化富勒烯自由基或富勒烯阴离子来生成富勒烯阳离子。结果表明，阳离子富勒烯可用于富勒烯的官能化，特别是可用于合成非环状1,2-二（有机）[60]富勒烯衍生物，该衍生物可通过分子内1,4-芳基的迁移而选择性制备。从硅原子到富勒烯核心的芳基。
• Silylmethylations of C60 with Grignard Reagents: Selective Synthesis of HC60CH2SiMe2Y and C60(CH2SiMe2Y)2 with Selection of Solvents
  作者：Hideo Nagashima、Hiroshi Terasaki、Eiji Kimura、Katsumasa Nakajima、Kenji Itoh

  DOI：10.1021/jo00085a007

  日期：1994.3

  Addition reactions of Me2SiYCH2MgCl (1) to C60 provided two products, HC60CH2SiYMe2 (2) and [Me2YSiCH2]2C60 (3) (Y = Me, H, CH=CH2, Ph, O(i)Pr). Selective preparation of either 2 or 3 was accomplished by selection of the solvent; 2 was formed in THF, whereas 3 was produced in toluene.
• Regioselective Synthesis of 1,4-Di(organo)[60]fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction
  作者：Yutaka Matsuo、Akihiko Iwashita、Yoko Abe、Chang-Zhi Li、Keiko Matsuo、Masahiko Hashiguchi、Eiichi Nakamura

  DOI：10.1021/ja8041299

  日期：2008.11.19

  Monoaddition of Grignard reagents, in particular tri(organo)silylmethyl magnesium chlorides, to [60]fullerene took place smoothly in the presence of dimethylformamideto produce (organo)(hydro)[60]fullerenes, (C60RH)-H-1, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R-, which was then alkylated to obtain 58 pi-electron di(organo)[60]fullerenes, (C60RR2)-R-1, in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo)[60] fullerenes bearing the same or different organic addends on the [60] fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.