2,6-bis{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}anthraquinone | 345915-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}anthraquinone
• 英文别名: 2,6-Bis[2-[tert-butyl(diphenyl)silyl]oxyethoxy]anthracene-9,10-dione
• CAS: 345915-46-0
• 化学式: C₅₀H₅₂O₆Si₂
• 分子量: 805.13
• InChiKey: BWQXHVDCGZYKGR-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  795.4±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-bis{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}anthraquinone 在 吡啶 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 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 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2,6-bis{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}anthraquinone
  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

• Extreme Conformational Constraints in π-Extended Tetrathiafulvalenes:  Unusual Topologies and Redox Behavior of Doubly and Triply Bridged Cyclophanes
  作者：Christian A. Christensen、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1021/ja062358m

  日期：2006.8.1

  Doubly and triply bridged 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (ex-TTF) derivatives have been synthesized. Key steps are the generation and macrocyclization reactions of ex-TTF-dithiolate reagents. The X-ray crystal structures of the doubly bridged cyclophanes 15 and 16 and the triply bridged system 23 show that the saddle-like conformation of the ex-TTF framework is enhanced by the

  已经合成了双桥和三桥 9,10-双 (1,3-二硫醇-2-亚基)-9,10-二氢蒽 (ex-TTF) 衍生物。关键步骤是 ex-TTF-dithiolate 试剂的生成和大环化反应。双桥环芳烃 15 和 16 以及三桥系统 23 的 X 射线晶体结构表明，二硫醇环之间的短桥增强了 ex-TTF 骨架的鞍状构象。与之前所有的 ex-TTF 衍生物（显示单个准可逆的双电子氧化波，D0 --> D2+）不同，环芳烃的循环伏安法显示了两个可逆的单电子氧化步骤（D0 --> D*+ --> D2+)，半波电位 (E2(1/2) - E1(1/2)) 之间的差异为 0.22-0.26 V。在不受限制的 ex-TTF 系统（包括单桥环芳烃）中驱动第二个氧化过程的构象变化和芳香性的增加已被多重桥接阻止。自由基阳离子物种产生了一个非常宽的低能带（λmax = 2175 和 2040 nm，分别为 15 和
• Molecular Saddles. 7.¹ New 9,10-Bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene Cyclophanes:  Synthesis, Redox Properties, and X-ray Crystal Structures of Neutral Species and a Dication Salt
  作者：Christian A. Christensen、Andrei S. Batsanov、Martin R. Bryce、Judith A. K. Howard

  DOI：10.1021/jo001524k

  日期：2001.5.1

  dication salt 18(2+)(I(3)(-))(2).(I(2))(0.5). For comparative purposes, the structures are also reported for the precursor diol 15 and its dication salt 15(2+)(ClO(4)(-))(2), which was obtained by electrocrystallization. In the neutral cyclophanes 18-20, the 9,10-bis(1,3-dithiol-2-ylidene)-9, 10-dihydroanthracene moieties adopt a saddle-shaped conformation. The overall measure of folding, the dihedral angle

  我们报道了通过二醇15和16与1，4-苯二羰基氯的酯形成大环化反应合成环烷18-20。化合物18和19在循环伏安图中显示两电子准可逆氧化波，分别在E（ox）（pa）0.52和0.47 V处产生指示物质（与乙腈中的Ag / AgCl相比），而2 + 2产物20在E（o）（x）（pa）0.51 V处经历单四电子氧化过程。报道了化合物18-20和指示盐18（2 +）（I（3））的X射线晶体结构（-））（2）。（I（2））（0.5）。为了进行比较，还报道了前体二醇15及其指示盐15（2 +）（ClO（4）（-））（2）的结构，该结构是通过电结晶获得的。在中性环烷18-20中，9,10-双（1,3-二硫醇-2-亚烷基）-9 10-二氢蒽部分采用鞍形构象。S（1）C（16）C（17）S（2）和S（5）C（21）C（22）S（6）平面之间的二面角（θ）折叠的总体度量为在15和18（分别为87.6度和83
• A (π-Extended Tetrathiafulvalene)−Fluorene Conjugate. Unusual Electrochemistry and Charge Transfer Properties:  The First Observation of a Covalent D²⁺−σ−A^•^- Redox State¹
  作者：Dmitrii F. Perepichka、Martin R. Bryce、Igor F. Perepichka、Svetlana B. Lyubchik、Christian A. Christensen、Nicolas Godbert、Andrei S. Batsanov、Eric Levillain、Eric J. L. McInnes、Jing P. Zhao

  DOI：10.1021/ja012518o

  日期：2002.11.1

  amphoteric TTFAQ-sigma-A compounds (TTFAQ = 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene, sigma = saturated spacer, A = polynitrofluorene acceptor) is reported. Their solution redox behavior is characterized by three single-electron reduction and one two-electron oxidation waves. Electrochemical quasireversibility of the TTFAQ(2+) state and a low E(ox) - E(red) gap ( approximately 0.25 V) for

  报道了新型电化学两性 TTFAQ-sigma-A 化合物（TTFAQ = 9,10-双（1,3-二硫醇-2-亚基）-9,10-二氢蒽，sigma = 饱和间隔基，A = 聚硝基芴受体）的合成. 它们的溶液氧化还原行为的特点是三个单电子还原波和一个双电子氧化波。3-(9-dicyanomethylene-4,5,7-trinitrofluorene-2-sulfonyl)-propionic 的 TTFAQ(2+) 状态和低 E(ox) - E(red) 间隙（约 0.25 V）的电化学准可逆性酸 2-[10-(4,5-二甲基-[1,3]dithiol-2-ylidene)-9,10-dihydroanthracen-9-ylidene]-5-methyl-[1,3]dithiol-4-ylmethyl酯 (10) 能够电化学生成迄今为止未知的瞬态 D(2+)-sigma-A(.-) 状态，