9,10-bis(1,3-dithiol-2-ylidene)-2,6-bis(2-hydroxyethyloxy)-9,10-dihydroanthracene | 500004-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(1,3-dithiol-2-ylidene)-2,6-bis(2-hydroxyethyloxy)-9,10-dihydroanthracene
• 英文别名: 2-[9,10-Bis(1,3-dithiol-2-ylidene)-6-(2-hydroxyethoxy)anthracen-2-yl]oxyethanol
• CAS: 500004-04-6
• 化学式: C₂₄H₂₀O₄S₄
• 分子量: 500.684
• InChiKey: SGSAYPUILTYBHM-UHFFFAOYSA-N

物化性质

• 沸点：
  717.7±60.0 °C(predicted)
• 密度：
  1.517±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯甲酰乙酸乙酯 、 9,10-bis(1,3-dithiol-2-ylidene)-2,6-bis(2-hydroxyethyloxy)-9,10-dihydroanthracene 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到9,10-bis(1,3-dithiol-2-ylidene)-2,6-bis(1,4,8-trioxa-5,7-dioxodecyl)-9,10-dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of Bingel-type Methanofullerene−π-Extended-TTF Diads and Triads

  摘要：

  Novel C-60/pi-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D(2)A (14a-c) and DA(2) (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C-60 affords the respective C-60-exTTF diads (26a-c) together with the triad C-60-exTTF-C-60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C-60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C-60(-)-exTTF(.+)) has been observed for compounds 14a-c.

  DOI：

  10.1021/jo020412l
• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 咪唑 、 正丁基锂 、 四丁基氟化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 9,10-bis(1,3-dithiol-2-ylidene)-2,6-bis(2-hydroxyethyloxy)-9,10-dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of Bingel-type Methanofullerene−π-Extended-TTF Diads and Triads

  摘要：

  Novel C-60/pi-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D(2)A (14a-c) and DA(2) (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C-60 affords the respective C-60-exTTF diads (26a-c) together with the triad C-60-exTTF-C-60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C-60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C-60(-)-exTTF(.+)) has been observed for compounds 14a-c.

  DOI：

  10.1021/jo020412l

文献信息

• Synthesis and Properties of Bingel-type Methanofullerene−π-Extended-TTF Diads and Triads
  作者：Susana González、Nazario Martín、Dirk M. Guldi

  DOI：10.1021/jo020412l

  日期：2003.2.1

  Novel C-60/pi-extended tetrathiafulvalene (exTTF) diads (12a-c) and triads [D(2)A (14a-c) and DA(2) (25, 27a-c)] have been synthesized by the Bingel cyclopropanation reaction of the respective exTTF-containing malonates and [60]fullerene. The reaction of exTTF-bismalonates with C-60 affords the respective C-60-exTTF diads (26a-c) together with the triad C-60-exTTF-C-60 (25, 27a-c) and a regioisomeric mixture of bisadducts (28b-c). Theoretical calculations (PM3) predict the favored geometry for triads 14a-c depending upon the orientation (up and down) of the 1,3-dithiole rings in the exTTFs, as well as the more stable regioisomers for the bisadducts 28. Cyclic voltammetry measurements reveal that C-60 and exTTF units do not intereact in the ground state. Compounds 26a-c and 27a-c are not electrochemically stable. A photoinduced electron transfer leading to the formation of the radical pair (C-60(-)-exTTF(.+)) has been observed for compounds 14a-c.