eee-C63(COOEt)6 | 155420-08-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: eee-C63(COOEt)6
• 英文别名: 27,45:31,32:55,56-tris-[bis(ethoxycarbonyl)methano]-27,45,31,32,55,56-hexahydro[60]fullerene
• CAS: 155420-08-9
• 化学式: C₈₁H₃₀O₁₂
• 分子量: 1195.12
• InChiKey: MFUIGBUQAJZFDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  93
• 可旋转键数：
  18
• 环数：
  35.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  eee-C63(COOEt)6 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Fullerenemalonates inhibit amyloid beta aggregation, in vitro and in silico evaluation

  摘要：

  合成新的无毒纳米材料，具有高抗淀粉样蛋白纤维形成效果，体外和体内模拟。

  DOI：

  10.1039/c8ra07643j
• 作为产物：
  描述：

  溴代丙二酸二乙酯 、 31,32:55,56-bis[bis(ethoxycarbonyl)methano]-31,32,55,56-tetrahydro[60]fullerene 以40%的产率得到eee-C63(COOEt)6
  参考文献：
  名称：

  Redox and Excitation Studies with C60-Substituted Malonic Acid Diethyl Esters

  摘要：

  Flash photolytic formation of excited triplet states, their consecutive reductive quenching with diazabicyclooctane (DABCO), and pulse radiolytic formation of pi-radical anions of various Cao-derivatives have been recorded. The fullerenes were functionalized via single, double, and triple cyclopropylation of C-60 with bromomalonic acid diethyl ester. Flash photolytic irradiation at 308 nm of these C-60 derivatives in toluene solution yielded triplet excited states which exhibited a strong blue shift of lambda(max) by nearly 100 nm as compared to plain C-3(60). This is rationalized in terms of a gradual destruction of the fullerene's pi-system with an increasing number of bis(ethoxycarbonyl)methylene groups. The blue shift coincides with a significant slow down for the rate of reductive quenching of the excited triplet states by DABCO, i.e., 1.3 x 10(6) M(-1) s(-1) vs 2.5 x 10(9) M(-1) s(-1) for the quenching of equatorial-(C-3(60))[C(COOEt)(2)](3) and C-3(60), respectively. The radical-induced reduction of functionalized C-60 has been studied in a toluene/acetone/2-propanol mixture by means of time-resolved pulse radiolysis with measurements being conducted in the characteristic near-IR region. An almost linear dependence is obtained between the energy of the most significant IR-pi-radical anion band versus the number of bis(ethoxycarbonyl)methylene groups at the fullerene core, with the respective lambda(max) ranging from 1080 nm for C-60(.-) to 1015 nm for equatorial-(C-60(.-))[C(COOEt)(2)](3). A corresponding trend emerges from cyclic voltammetry measurements on the redox potential in toluene/2-propanol. They show a difference of 330 mV between the formation of C-60(.-) (E(1/2) = -0.55 V vs SCE) and the first reduction of equatorial-C-60-[C(COOEt)(2)](3) (E(1/2) = -0.86 V vs SCE). It appears that all these physicochemical parameters very sensitively reflect the site and degree of functionalization of C-60.

  DOI：

  10.1021/j100023a013

文献信息

• Hirsch, Andreas; Lamparth, Iris; Karfunkel, Heinrich R., Angewandte Chemie, 1994, vol. 106, # 4, p. 453 - 455
  作者：Hirsch, Andreas、Lamparth, Iris、Karfunkel, Heinrich R.

  DOI：——

  日期：——
• Redox and Excitation Studies with C60-Substituted Malonic Acid Diethyl Esters
  作者：Dirk M. Guldi、Hartmut Hungerbuehler、Klaus-Dieter Asmus

  DOI：10.1021/j100023a013

  日期：1995.6

  Flash photolytic formation of excited triplet states, their consecutive reductive quenching with diazabicyclooctane (DABCO), and pulse radiolytic formation of pi-radical anions of various Cao-derivatives have been recorded. The fullerenes were functionalized via single, double, and triple cyclopropylation of C-60 with bromomalonic acid diethyl ester. Flash photolytic irradiation at 308 nm of these C-60 derivatives in toluene solution yielded triplet excited states which exhibited a strong blue shift of lambda(max) by nearly 100 nm as compared to plain C-3(60). This is rationalized in terms of a gradual destruction of the fullerene's pi-system with an increasing number of bis(ethoxycarbonyl)methylene groups. The blue shift coincides with a significant slow down for the rate of reductive quenching of the excited triplet states by DABCO, i.e., 1.3 x 10(6) M(-1) s(-1) vs 2.5 x 10(9) M(-1) s(-1) for the quenching of equatorial-(C-3(60))[C(COOEt)(2)](3) and C-3(60), respectively. The radical-induced reduction of functionalized C-60 has been studied in a toluene/acetone/2-propanol mixture by means of time-resolved pulse radiolysis with measurements being conducted in the characteristic near-IR region. An almost linear dependence is obtained between the energy of the most significant IR-pi-radical anion band versus the number of bis(ethoxycarbonyl)methylene groups at the fullerene core, with the respective lambda(max) ranging from 1080 nm for C-60(.-) to 1015 nm for equatorial-(C-60(.-))[C(COOEt)(2)](3). A corresponding trend emerges from cyclic voltammetry measurements on the redox potential in toluene/2-propanol. They show a difference of 330 mV between the formation of C-60(.-) (E(1/2) = -0.55 V vs SCE) and the first reduction of equatorial-C-60-[C(COOEt)(2)](3) (E(1/2) = -0.86 V vs SCE). It appears that all these physicochemical parameters very sensitively reflect the site and degree of functionalization of C-60.
• Fullerenemalonates inhibit amyloid beta aggregation, <i>in vitro</i> and <i>in silico</i> evaluation
  作者：Martínez-Herrera Melchor、Figueroa-Gerstenmaier Susana、García-Sierra Francisco、Beltrán Hiram I.、Rivera-Fernández Norma、Lerma-Romero Jorge A.、López-Camacho Perla Y.、Basurto-Islas Gustavo

  DOI：10.1039/c8ra07643j

  日期：——

  Synthesis of new non toxic nanomaterials, with high anti-amyloid fibrils formation effect, in vitro and in silico.

  合成新的无毒纳米材料，具有高抗淀粉样蛋白纤维形成效果，体外和体内模拟。