2,2-[60]fullerenobutanal | 367926-62-3

• 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: 2,2-[60]fullerenobutanal
• 英文别名: 2,3-[6-]fullerobutanal
• CAS: 367926-62-3
• 化学式: C₆₄H₆O
• 分子量: 790.751
• InChiKey: SSDKISVFFBOLPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  65.0
• 可旋转键数：
  2.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯胺 、 2,2-[60]fullerenobutanal 在 3 A molecular sieve 作用下， 以 苯 为溶剂， 反应 48.0h， 以100%的产率得到
  参考文献：
  名称：

  Synthesis and transformation of a novel methano[60]fullerene having a formyl group

  摘要：

  The reaction of [60]fullerene with a dimethylsulfonium alpha -formylalkylide gave a novel methano[60]fullerene having a formyl group at the bridge-head carbon, This 2.2-[60]fulleroalkanal was readily converted into a variety of N-aryl-2,2-[60]fulleroaldimines by condensation with aromatic amines: one of them showed efficient quenching of the fluorescence of the [60]fullerene core, due to a photoinduced intramolecular electron transfer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00944-3
• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以79%的产率得到2,2-[60]fullerenobutanal
  参考文献：
  名称：

  An Alternative Type of Fullerene Products from the Reaction of [60]Fullerene with Alkoxides and Subsequent Derivatization

  摘要：

  Reaction of [60]fullerene with freshly prepared RCH(2)CH(2)ONa/RCH(2)CH(2)OH (R = H, Me, Et, Ph) in anhydrous toluene in the presence of air unexpectedly afforded fullerene products with a C(60)-fused tetrahydrofuran ring Skeleton and an acetal moiety, which could be further transformed into C(60)-fused dihydrofurans, tolyl-substituted C(60)-fused tetrahydrofuran, and methanofullerenes bearing a formyl group by boron trifluoride etherate. Possible reaction mechanisms are proposed to explain the formation of different fullerene products.

  DOI：

  10.1021/jo9005848

文献信息

• A General Method for the Synthesis of 2,2-[60]Fullerenoalkanals: The Reaction of [60]Fullerene with 2-Bromoenol Silyl Ethers
  作者：Kazuhiko Saigo、Hiroshi Ito、Yusuke Kishi、Yohei Nishikawa、Tomonori Tada、Yasuhiro Ishida

  DOI：10.1055/s-0030-1258112

  日期：2010.7

  synthesized by the fluoride ion-mediated reaction of [60]fullerene with 2-bromoenol silyl ethers, which were easily prepared by 2-bromination of the corresponding enol silyl ethers. The reactivity differed significantly depending on the stability of the 2-bromoenol silyl ethers. High yield and selectivity were achieved for the reaction of 2-bromoenol trimethylsilyl ethers under mild conditions (KF/18-crown-6-ether)

  通过氟离子介导的 [60] 富勒烯与 2-溴烯醇甲硅烷基醚的反应合成了五种 2,2-[60] 富勒烯烷醛，该反应很容易通过相应烯醇甲硅烷基醚的 2-溴化制备。反应性显着不同，这取决于 2-溴烯醇甲硅烷基醚的稳定性。2-溴烯醇三甲基甲硅烷基醚在温和条件下（KF/18-crown-6-ether）的反应实现了高产率和选择性。另一方面，稳定的 2-溴烯醇叔丁基二甲基甲硅烷基醚的反应需要使用更具反应性的四丁基氟化铵作为氟离子源。
• Copper-Catalyzed Reaction of C₆₀ with Tertiary Amines for the Preparation of Spiro-Linked Methanofullerenes and Fullerenoalkanals
  作者：Yong-Jian Liu、Jie Ge、Chun-Bao Miao、Hai-Tao Yang

  DOI：10.1021/acs.joc.9b00335

  日期：2019.5.17

  CuI-catalyzed reaction of C60 with tertiary amines by using air as the sole oxidant has been developed. Spiro-linked methanofullerenes bearing cyclic amides and fullerenoalkanals can be obtained selectively using the cyclic and acyclic amines as starting materials, respectively. The reactions show a wide functional group tolerance. In addition, four ([6,6]-phenyl-C61-butyric acid methyl ester) analogues

  通过使用空气作为唯一的氧化剂，已开发出CuI催化的C 60与叔胺的反应。分别使用环状和非环状胺作为起始原料，可以选择性地获得带有环状酰胺和富勒烯烷醛的螺旋连接的甲基富勒烯。反应显示出宽泛的官能团耐受性。另外，通过开发的方法可以容易地制备四个（[6,6]-苯基-C 61-丁酸甲酯）类似物。