2-hydroxymethylthieno<3,2-e:4,5-e'>di<1>benzothiophene | 157792-55-7

• 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: 2-hydroxymethylthieno<3,2-e:4,5-e'>di<1>benzothiophene
• 英文别名: 2-hydroxymethyltrithia<5>heterohelicene；2-hydroxymethyl<5>thiaheterohelicene；2-hydroxymethyl[5]thiaheterohelicene；2-hydroxymethylthieno[3,2-e:4,5-e']di[1]benzothiophene；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-octaen-5-ylmethanol；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-octaen-5-ylmethanol
• CAS: 157792-55-7；177314-18-0；191940-49-5
• 化学式: C₁₇H₁₀OS₃
• 分子量: 326.464
• InChiKey: PEJUVLXEYOJZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethylthieno<3,2-e:4,5-e'>di<1>benzothiophene 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 生成
  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：

  <5>thiaheterohelicene-2-aldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 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

文献信息

• Peptidehelicenes in solution and gel: chiral discrimination through interactions between two types of helixes
  作者：Hiroko Nakagawa、Kumiko Ohtsuka、Katsuhito Sugahara、Chika Kobayashi、Yuichi Masuoka、Koh-ichi Yamada、Masami Kawase

  DOI：10.1016/j.tetasy.2010.03.040

  日期：2010.4

  Helical [5]thiaheterohelicene 5HM, which rapidly interconverts between P and M enantiomers in solution, was connected to helical L-phenylalanine oligomers with an ester linkage to give peptidehelicenes (5Fn, where n: number of bonded phenylalanines). The characteristics of 5F4 and 5F5 with two types of helixes in a molecule were investigated, particularly in comparison with those of 5F1-5F3 with an incomplete coil of a peptide moiety. L-Phenylalanine peptide chains induced a shift in the equilibrium between the P and M helixes of 5HM toward the P side for all the 5Fns examined. The enantiomeric excess (ee) of the P form increased with a decrease in temperature, together with an elongation of the peptide chains. 5F4 and 5F5 in hot solutions of some solvents formed a gel at room temperature, whereas 5F1-5F3 showed no such behavior. In this gel, the stable helical form of the 5HM moiety in 5F4 and 5F5 was observed to be the M form in contrast to that in their solutions. (C) 2010 Elsevier Ltd. All rights reserved.
• 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
• Photochemical synthesis and structural properties of high membered thiohelicenes
  作者：Tullio Caronna、Roberta Sinisi、Luciana Malpezzi、Stefano V. Meille、Andrea Mele、Marinella Catellani

  DOI：10.1039/b002581j

  日期：——

  A general photochemical synthesis of large thiohelicenes containing nine and eleven rings is discussed along with the organisation of racemic thiohelicenes in crystals: heterochiral assembling is dominant except in the nine-ring system where interactions involving terminal ring S atoms favour the segregation of close-packed homochiral molecules in planes.

  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。