1,4-diallyl-1,4-dihydro[60]fullerene

• 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: 1,4-diallyl-1,4-dihydro[60]fullerene
• 化学式: C₆₆H₁₀
• 分子量: 802.805
• InChiKey: YGOVOWQKCKKCMG-HOAYPZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  66
• 可旋转键数：
  4
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 1,2-二氢[60]富勒烯 在 四丁基氢氧化铵 作用下， 以 甲醇 、 苯甲腈 为溶剂， 反应 2.0h， 以49%的产率得到1,4-diallyl-1,4-dihydro[60]fullerene
  参考文献：
  名称：

  Alkylation of Dihydrofullerenes

  摘要：

  The falleride dianions C-60(2-) and C-70(2-) were generated by deprotonation of the corresponding hydrogenated fallerenes, 1,2-C60H2 and 1,2-C70H2. These anions were prepared in the presence of a variety of alkylating agents, and mono- or dialkylated products were obtained. Alkylation was not successful with sulfonate ester alkylating agents. Deprotonation of monoalkylated compounds, followed by second alkylation. with a different alkylating agent, produced heterodialkylated compounds. The monoalkyated material was invariably the 1,2-isomers, while the dialkylated materials were generally 1,4-isomers, although some 1,2-isomer was observed in the C-70 context. The major product from alkylation of C-70(2-) was the 7,23-isomer 13a, a structure where the alkylation took place near the equator of the fullerene cage, rather than at the more strained carbons near the poles.

  DOI：

  10.1021/jo020216e

文献信息

• Regioselective Unsymmetrical Tetraallylation of C₆₀ through Palladium Catalysis
  作者：Masakazu Nambo、Atsushi Wakamiya、Shigehiro Yamaguchi、Kenichiro Itami

  DOI：10.1021/ja9071173

  日期：2009.10.28

  A Pd-catalyzed tetraallylation of C(60) that selectively occurs with an unsymmetrical addition pattern has been established. Treatment of C(60) with CH(2)=CHCH(2)Cl, CH(2)=CHCH(2)SnBu(3), and PdCl(2)[P(OPh)(3)](2) in 1,2-Cl(2)C(6)H(4) at 50 degrees C afforded the tetraallylated fullerene in 74% yield with virtually complete regioselectivity. Mechanistic investigations showed that (i) tetraallylation

  已经建立了 Pd 催化的 C(60) tetraallylation 有选择性地发生与不对称添加模式。用 CH(2)=CHCH(2)Cl、CH(2)=CHCH(2)SnBu(3) 和 PdCl(2)[P(OPh)(3)](2) 处理 C(60) 1,2-Cl(2)C(6)H(4) 在 50 摄氏度下以 74% 的产率提供了四烯丙基化的富勒烯，具有几乎完全的区域选择性。机理研究表明，（i）四烯丙基化通过连续的亲核/亲电烯丙基化进行[可能通过双（pi-烯丙基）钯中间体]和（ii）空间（对于第一次二烯丙基化）和电子（对于第二次二烯丙基化）因子都是负责高区域选择性。
• Alkylation of Dihydrofullerenes
  作者：Mark S. Meier、Robert G. Bergosh、Megan E. Gallagher、H. Peter Spielmann、Zhongwen Wang

  DOI：10.1021/jo020216e

  日期：2002.8.1

  The falleride dianions C-60(2-) and C-70(2-) were generated by deprotonation of the corresponding hydrogenated fallerenes, 1,2-C60H2 and 1,2-C70H2. These anions were prepared in the presence of a variety of alkylating agents, and mono- or dialkylated products were obtained. Alkylation was not successful with sulfonate ester alkylating agents. Deprotonation of monoalkylated compounds, followed by second alkylation. with a different alkylating agent, produced heterodialkylated compounds. The monoalkyated material was invariably the 1,2-isomers, while the dialkylated materials were generally 1,4-isomers, although some 1,2-isomer was observed in the C-70 context. The major product from alkylation of C-70(2-) was the 7,23-isomer 13a, a structure where the alkylation took place near the equator of the fullerene cage, rather than at the more strained carbons near the poles.