1-(chlorodimethylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene | 168129-08-6

• 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-(chlorodimethylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene
• 英文别名: chloro-(9H-(C60-Ih)[5,6]fulleren-1-ylmethyl)-dimethylsilane
• CAS: 168129-08-6
• 化学式: C₆₃H₉ClSi
• 分子量: 829.303
• InChiKey: FWVLZUNINLESBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.58
• 重原子数：
  65
• 可旋转键数：
  2
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.08
• 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-(chlorodimethylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene 在 水 作用下， 生成 9H-(C60-Ih)[5,6]fulleren-1-ylmethyl-hydroxy-dimethylsilane
  参考文献：
  名称：

  Chlorosilanes and Silyl Triflates Containing C60 as a Partial Structure. A Versatile Synthetic Entry Linking the C60 Moieties with Alcohols, Phenols, and Silica

  摘要：

  DOI：

  10.1021/jo00121a004
• 作为产物：
  描述：

  1-(Isopropoxydimethylsilylmethyl)-1,9-dihydro(C60-I_h)[5,6]fullerene 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(chlorodimethylsilylmethyl)-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

• Chlorosilanes and Silyl Triflates Containing C60 as a Partial Structure. A Versatile Synthetic Entry Linking the C60 Moieties with Alcohols, Phenols, and Silica
  作者：Hideo Nagashima、Hiroshi Terasaki、Yoshihiro Saito、Kiyokatsu Jinno、Kenji Itoh

  DOI：10.1021/jo00121a004

  日期：1995.8
• 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.