1,2-dihydro<60>fullerene-1-(prop-2'-ene)

• 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: 1,2-dihydro<60>fullerene-1-(prop-2'-ene)
• 英文别名: 1-allyl-1,2-dihydro[60]fullerene；2-allyl-1,2-dihydro[60]fullerene；9-prop-2-enyl-1H-(C60-Ih)[5,6]fullerene
• 化学式: C₆₃H₆
• 分子量: 762.741
• InChiKey: LLOPQTZXCVJIRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  63
• 可旋转键数：
  2
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  足球烯 、 3-溴丙烯 在 锰 、 [1,2-双(二苯基膦)乙烷]二氯钴(II) 、 水 作用下， 以 邻二氯苯 为溶剂， 反应 86.0h， 以74%的产率得到1,2-dihydro<60>fullerene-1-(prop-2'-ene)
  参考文献：
  名称：

  [60]富勒烯与活性烷基溴的钴催化加氢烷基化：单烷基化富勒烯的选择性合成

  摘要：

  C(60) 与反应性烷基溴化物 1 (RBr) 在 Mn 还原剂和 H(2)O 在环境温度下的共催化加氢烷基化得到单烷基化的 C(60) (2) 以良好到高产率。在 Ar 气氛下使用 CoLn/Mn/H(2)O 是目前转型成功的关键。该反应最有可能通过 Co(0 或 I) 配合物促进生成自由基 (R(•))，然后添加到 C(60)。这种加氢烷基化方法适用于合成附有 C(60) (2l) 的锌卟啉、附有 C(60) (2m) 的树枝状聚合物和富勒烯二聚体 (2n)，这些化合物不容易通过先前已知的方法获得。

  DOI：

  10.1021/ja204982w

文献信息

• Addition of Group 14 organometallic compounds to C60 via photoinduced electron transfer. Direct detection of radical ion pair intermediates
  作者：Shunichi Fukuzumi、Tomoyoshi Suenobu、Mamoru Fujitsuka、Osamu Ito、Takayuki Tonoi、Shoji Matsumoto、Koichi Mikami

  DOI：10.1016/s0022-328x(98)00929-2

  日期：1999.2

  indicates that the photoreduction proceeds via photoinduced electron transfer from the electron donors to the triplet excited state of C60. The radical ion pair generated in the photoinduced electron transfer from ketene silyl acetal to the triplet excited state of C60 has been successfully detected as transient absorption spectra in the visible and near-IR region with use of the laser flash photolysis.

  C 60与14族有机金属的碳-碳键形成是通过从作为电子供体的14族有机金属化合物向C 60的三重激发态进行光致电子转移而实现的。在这项研究中使用的电子供体是乙烯酮甲硅烷基乙缩醛和烯丙基锡烷。当非对称烯丙基锡烷，例如prenyltributyltin（ME 2 CCHCH 2 SnBu 3）采用，烯丙基基团是在选择性地引入α位上，以产生Ç 60 -1,2-CH 2 CHCMe 2的照射下可见光，无γ加合物已形成。这种区域选择性是prenyltributyltin通过电子转移，其中CC的反应的特性δ的SnC键的裂解之后键形成发生。根据量子产率对电子给体浓度的依赖性以及电子给体对C 60的三重态激发态的猝灭与对电子转移过程预测的速率常数之间的比较，可以确定观察到的速率常数。通过从电子供体到C 60的三重激发态的光诱导电子转移进行光还原。从乙烯酮甲硅烷基缩醛光诱导电子转移到C 60的三重激发态时产生的自由基对
• Monoalkylation of C₆₀ and C₇₀ with Zn and Active Alkyl Bromides
  作者：Zhongwen Wang、Mark S. Meier

  DOI：10.1021/jo020563o

  日期：2003.4.1

  We report a convenient and simple solution-phase electron-transfer reaction Of C-60 with zinc and alpha-bromoacetonitrile, alpha-bromo acetate esters, allyl bromide, benzyl bromide and a-bromo ketones in DDIF, with which different types of monoalkylated C-60 derivatives can be prepared. When this method is employed with C-70, 2-carbomethoxymethyl-1,2-dihydro[70]fullerene (isomer 5a) is produced as one of the two 1,2-monoalkylated C-70 isomers, together with the first 5,6-monoalkylated C-70 derivative.
• 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.
• Cobalt-Catalyzed Hydroalkylation of [60]Fullerene with Active Alkyl Bromides: Selective Synthesis of Monoalkylated Fullerenes
  作者：Shirong Lu、Tienan Jin、Ming Bao、Yoshinori Yamamoto

  DOI：10.1021/ja204982w

  日期：2011.8.17

  present transformation. The reaction most probably proceeds through the Co(0 or I) complex-promoted generation of a radical (R(•)) followed by addition to C(60). This hydroalkylation method was applied to the synthesis of zinc porphyrin attached C(60) (2l), dendrimer attached C(60) (2m), and fullerene dimer (2n), which were not easily available through the previously known methods.

  C(60) 与反应性烷基溴化物 1 (RBr) 在 Mn 还原剂和 H(2)O 在环境温度下的共催化加氢烷基化得到单烷基化的 C(60) (2) 以良好到高产率。在 Ar 气氛下使用 CoLn/Mn/H(2)O 是目前转型成功的关键。该反应最有可能通过 Co(0 或 I) 配合物促进生成自由基 (R(•))，然后添加到 C(60)。这种加氢烷基化方法适用于合成附有 C(60) (2l) 的锌卟啉、附有 C(60) (2m) 的树枝状聚合物和富勒烯二聚体 (2n)，这些化合物不容易通过先前已知的方法获得。