9,10-bis(4,5-dimethylthio-1,3-dithiol-2-ylidene)-2-hydroxymethyl-9,10-dihydroanthracene | 148117-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(4,5-dimethylthio-1,3-dithiol-2-ylidene)-2-hydroxymethyl-9,10-dihydroanthracene
• 英文别名: [9,10-Bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]anthracen-2-yl]methanol
• CAS: 148117-63-9
• 化学式: C₂₅H₂₂OS₈
• 分子量: 594.977
• InChiKey: RLBJCQDDGDOFQG-UHFFFAOYSA-N

物化性质

• 沸点：
  693.8±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  223
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9,10-bis(4,5-dimethylthio-1,3-dithiol-2-ylidene)-2-hydroxymethyl-9,10-dihydroanthracene 在 sodium azide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-[2-(Azidomethyl)-10-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]anthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
  参考文献：
  名称：

  叠氮基-exTTFs与C60的加成反应：合成富勒三唑啉和氮杂富勒烯类电活性二元化合物。

  摘要：

  [结构：见正文]叠氮基exTTFs与C（60）的加成反应提供了电活性的全三氮唑啉和azafulleroid dyads，它们起着两性氧化还原系统的作用。荧光实验和瞬态吸收光谱表明，富勒烯部分的激发导致自由基对的寿命比以前报道的相关富三唑啉的寿命高2个数量级。

  DOI：

  10.1021/ol027473q
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 咪唑 、 正丁基锂 、 四丁基氟化铵 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(4,5-dimethylthio-1,3-dithiol-2-ylidene)-2-hydroxymethyl-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

• Cerrada, Elena; Bryce, Martin R.; Moore, Adrian J., Journal of the Chemical Society. Perkin transactions I, 1993, # 5, p. 537 - 538
  作者：Cerrada, Elena、Bryce, Martin R.、Moore, Adrian J.

  DOI：——

  日期：——
• 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.
• Addition Reaction of Azido-exTTFs to C₆₀:  Synthesis of Fullerotriazoline and Azafulleroid Electroactive Dyads
  作者：Susana González、Nazario Martín、Angela Swartz、Dirk M. Guldi

  DOI：10.1021/ol027473q

  日期：2003.2.1

  [structure: see text] The addition reaction of azido-exTTFs to C(60) affords electroactive fullerotriazoline and azafulleroid dyads, which behave as amphoteric redox systems. Fluorescence experiments and transient absorption spectroscopy reveal that excitation of the fullerene moiety leads to radical pair lifetimes that are 2 orders of magnitude higher than those previously reported for related fullerotriazolines

  [结构：见正文]叠氮基exTTFs与C（60）的加成反应提供了电活性的全三氮唑啉和azafulleroid dyads，它们起着两性氧化还原系统的作用。荧光实验和瞬态吸收光谱表明，富勒烯部分的激发导致自由基对的寿命比以前报道的相关富三唑啉的寿命高2个数量级。