1-(3-indolyl)-N-methyl-[60]fullereno-[1,9-c]pyrrolidine

• 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-(3-indolyl)-N-methyl-[60]fullereno-[1,9-c]pyrrolidine
• 英文别名: 1-(3-indolyl)-N-methyl-fullereno-C60-[1,9-c]pyrrolidine
• 化学式: C₇₁H₁₂N₂
• 分子量: 892.89
• InChiKey: AKUZKSVBQZKNJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.3
• 重原子数：
  73
• 可旋转键数：
  1
• 环数：
  35.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  芦竹碱 、 足球烯 以 甲苯 为溶剂， 反应 5.0h， 以24%的产率得到1-(3-indolyl)-N-methyl-[60]fullereno-[1,9-c]pyrrolidine
  参考文献：
  名称：

  Alkaloid−Fullerene Systems through Photocycloaddition Reactions¹

  摘要：

  The photocycloaddition of tertiary amines to [60]fullerene (C-60) is an interesting and useful reaction. We wished to extend the applications of this type of reaction through an investigation of the photoaddition of alkaloids to C-60 for the purpose of synthesizing novel and complex photoadducts that are difficult to obtain by usual methods. Irradiation of tazettine (2) or gramine (3) with Cao in toluene leads to formation of one monoadduct (6 or 7), whereas scandine (1a) or 10-hydroxyscandine (Ib) reacts with C-60 photochemically to give two products, the expected [6,6] monoadduct (5a, 5b) and a new type of monoadduct with a bis-[6, 6] closed structure (4a, 4b). These new structures were characterized by W-vis, FT-IR, H-1 NMR, C-13 NMR, H-1-H-1 COSY, ROESY, HMQC (heteronuclear multiple-quantum coherence), and HMBC (heteronuclear multiple-bond connectivity) spectroscopy. The techniques of time-of-flight secondary ion MS (TOF-SIMS) and field desorption MS (FD-MS) were used for the mass determination. He-3 NMR analysis of the product mixture from photoaddition of la to C-60 containing a He-3 atom (He-3@C-60) led to two peaks at -9.091 and -11.090 ppm relative to gaseous He-3, consistent with formation of a [6,6]-closed monoadduct and a bis-[6,6] closed adduct. Presumably, the bis-[6, 6] closed adducts are formed by an intramolecular [2 + 2] cycloaddition of the vinyl group to the adjacent 6,6-ring junction of C-60 after the initial photocycloaddition.

  DOI：

  10.1021/jo000156h

文献信息

• ——
  作者：V. P. Gubskaya、N. P. Konovalova、I. A. Nuretdinov、G. M. Fazleeva、L. Sh. Berezhnaya、F. G. Sibgatullina、I. P. Karaseva

  DOI：10.1023/a:1021363808113

  日期：——

  New fullerenopyrrolidines were synthesized by the three-component reactions of fullerene C-60, N-methylglycine, and aromatic aldehydes, viz., N,N-bis(2-chloroethyl)-4-aminobenzaldehyde, N-(2-chloroethyl)-N-methyl-4-aminobenzaldehyde, indole-3-carbaldehyde, 4-phenylbenzaldehyde, and anthracene-9-carbaldehyde. The structures of the resulting compounds were established by spectroscopic methods.
• Alkaloid−Fullerene Systems through Photocycloaddition Reactions¹
  作者：Li-Wei Guo、Xiang Gao、Dan-Wei Zhang、Shi-Hui Wu、Hou-Ming Wu、Yong-Jiang Li、Stephen R. Wilson、Christine F. Richardson、David I. Schuster

  DOI：10.1021/jo000156h

  日期：2000.6.1

  The photocycloaddition of tertiary amines to [60]fullerene (C-60) is an interesting and useful reaction. We wished to extend the applications of this type of reaction through an investigation of the photoaddition of alkaloids to C-60 for the purpose of synthesizing novel and complex photoadducts that are difficult to obtain by usual methods. Irradiation of tazettine (2) or gramine (3) with Cao in toluene leads to formation of one monoadduct (6 or 7), whereas scandine (1a) or 10-hydroxyscandine (Ib) reacts with C-60 photochemically to give two products, the expected [6,6] monoadduct (5a, 5b) and a new type of monoadduct with a bis-[6, 6] closed structure (4a, 4b). These new structures were characterized by W-vis, FT-IR, H-1 NMR, C-13 NMR, H-1-H-1 COSY, ROESY, HMQC (heteronuclear multiple-quantum coherence), and HMBC (heteronuclear multiple-bond connectivity) spectroscopy. The techniques of time-of-flight secondary ion MS (TOF-SIMS) and field desorption MS (FD-MS) were used for the mass determination. He-3 NMR analysis of the product mixture from photoaddition of la to C-60 containing a He-3 atom (He-3@C-60) led to two peaks at -9.091 and -11.090 ppm relative to gaseous He-3, consistent with formation of a [6,6]-closed monoadduct and a bis-[6,6] closed adduct. Presumably, the bis-[6, 6] closed adducts are formed by an intramolecular [2 + 2] cycloaddition of the vinyl group to the adjacent 6,6-ring junction of C-60 after the initial photocycloaddition.