<5>-thiaheterohelicene | 52875-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: <5>-thiaheterohelicene
• 英文别名: thieno<3,2-e:4,5-e'>di<1>benzothiophene；Trithia[5]heterohelicene；6,11,16-Trithiapentacyclo[10.7.0.02,10.03,7.015,19]nonadeca-1(12),2(10),3(7),4,8,13,15(19),17-octaene；6,11,16-trithiapentacyclo[10.7.0.02,10.03,7.015,19]nonadeca-1(12),2(10),3(7),4,8,13,15(19),17-octaene
• CAS: 52875-25-9；126452-73-1
• 化学式: C₁₆H₈S₃
• 分子量: 296.438
• InChiKey: ZJMYGBVCRPFUEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <5>-thiaheterohelicene 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 2-hydroxymethylthieno<3,2-e:4,5-e'>di<1>benzothiophene
  参考文献：
  名称：

  Photochemical synthesis and structural properties of high membered thiohelicenes

  摘要：

  讨论了一种普遍的光化学合成九环和十一环的大硫螺旋烃的方法，以及在晶体中外消旋硫螺旋烃的组装：异旋组装是主要过程，除了在九环系统中，在该系统中，涉及端环硫原子的相互作用有利于在平面中隔离紧密堆积的同旋分子。

  DOI：

  10.1039/b002581j
• 作为产物：
  描述：

  2-(2-thienylethenyl)benzo[1,2-b:4,3-b']dithiophene 生成 <5>-thiaheterohelicene
  参考文献：
  名称：

  Photochemical synthesis and structural properties of high membered thiohelicenes

  摘要：

  讨论了一种普遍的光化学合成九环和十一环的大硫螺旋烃的方法，以及在晶体中外消旋硫螺旋烃的组装：异旋组装是主要过程，除了在九环系统中，在该系统中，涉及端环硫原子的相互作用有利于在平面中隔离紧密堆积的同旋分子。

  DOI：

  10.1039/b002581j

文献信息

• Total conversion of racemic [5]thiaheterohelicene into a single enantiomer by a diastereoisomeric charge-transfer complex formation
  作者：Hiroko Nakagawa、Koh-ichi Yamada、Hiroshi Kawazura

  DOI：10.1039/c39890001378

  日期：——

  Racemic thieno[3,2-e:4,5-e′]di[1]benzothiophene was totally converted into a single enantiomer on crystallizing the charge-transfer complex with (S)-2-(2,4,5,7-tetranitro-9-fluorenylidene-amino-oxy)propionic acid; the structure of the complex was determined by X-ray crystallographic analysis.

  外消旋的噻吩并[3,2- e：4,5- e '] di [1]苯并噻吩在与（S）-2-（2,4,5,7）电荷转移配合物结晶时完全转化为单一对映体-四硝基-9-芴基-亚氨基-氧基）丙酸; 通过X射线晶体学分析确定配合物的结构。
• A second-order asymmetric transformation of racemic 2-hydroxymethyl[5]thiaheterohelicene into a single enantiomer upon uptake by bovine serum albumin
  作者：Koh-ichi Yamada、Rieko Ishii、Hiroko Nakagawa、Hiroshi Kawazura

  DOI：10.1016/0957-4166(96)00069-9

  日期：1996.3

  Racemic 2-hydroxymethylthieno[3,2-e:4,5-e']di[1]benzothiophene (2-HT) with a labile helical structure was converted into a P enantiomer upon uptake by bovine serum albumin (BSA) in 1% ethanol-water. The effect of the alteration of the molar ratio [2-HT]:[BSA] on UV and CD spectra of the 2-HT-BSA complex solution revealed that BSA possesses two different substrate-binding sites with a distinct ability to recognize chirality of enantiomers of 2-HT. The stability of the 2-HT-BSA complex and the chirality recognition at the two sites of BSA were evaluated by the equilibrium constants and the thermodynamic parameters which were obtained from the temperature-dependence of CD-absorptional intensities. BSA pretreated at 50 similar to 70 degrees C in an aqueous solution exhibited a great depression of ability in discriminating chirality between enantiomers of 2-HT, though it possessed slightly altered ability for uptake of 2-HT, in comparison with untreated BSA. (C) 1996 Elsevier Science Ltd
• Structure of the 1:1 Charge-Transfer Complex between Trithia[5]heterohelicene and 3,5-Dinitrobenzoic Acid. Deformation of Helicene Molecules in Crystals.
  作者：Koh-ichi Yamada、Eiji Oguma、Hiroko Nakagawa、Hiroshi Kawazura、Hiroshi Miyamae、Claus Nielsen、Shu Hai Zhao、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0438

  日期：——

  The crystal and molecular structure of the title charge-transfer (CT) complex was determined by X-ray crystallographic analysis. Thieno[3,2-e:4,5-e'] di[1]-benzothiophene ([5]TH) and 3,5-dinitrobenzoic acid are alternately aligned with a separation of ca. 3.8 Angstrom to produce one-dimensional columns along the B-axis. Within a column, the chirality of [5]TH, having a labile helical structure, is confined to either type of enantiomer. A comparison of three CT complexes of [5]TH with different accepters showed the propensity for planarity of the [5]TH molecule in the complex to increase with reduction of the electron affinity of the acceptors.