2,5-bis[(α-hydroxy-α,α-dimethyl)methyl]thiophene | 52098-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-bis[(α-hydroxy-α,α-dimethyl)methyl]thiophene
• 英文别名: 2-[5-(2-Hydroxypropan-2-yl)thiophen-2-yl]propan-2-ol
• CAS: 52098-08-5
• 化学式: C₁₀H₁₆O₂S
• 分子量: 200.302
• InChiKey: DBEUZGSEUHIMNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis[(α-hydroxy-α,α-dimethyl)methyl]thiophene 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 2.67h， 生成 calix[2]bipyrrole[2]thiophene
  参考文献：
  名称：

  Calix[2]bipyrrole[2]furan and Calix[2]bipyrrole[2]thiophene:  New Pyrrolic Receptors Exhibiting a Preference for Carboxylate Anions

  摘要：

  Heterocycles other than pyrrole, specifically bipyrrole, furan, and thiophene, have been used to construct two new, calixpyrrole-like anion receptors; binding studies, carried out by ITC in CH3CN, reveal a selectivity for "Y-shaped" anions, such as benzoate, over spherical ones, such as chloride.

  DOI：

  10.1021/ja038264j
• 作为产物：
  描述：

  2,7-二甲基-3,5-辛二炔-2,7-二醇 、 硫化氢 以50%的产率得到
  参考文献：
  名称：

  VOLKOV A. N.; SKVORTSOV YU. M.; KIND YU. V., ORGAN. SOEDIN. SERY. T. 2. RIGA, 1980, 50-52

  摘要：

  DOI：

文献信息

• Synthesis of expanded calix[n]pyrroles and their furan or thiophene analogues
  作者：Arumugam Nagarajan、Jae-Won Ka、Chang-Hee Lee

  DOI：10.1016/s0040-4020(01)00719-0

  日期：2001.8

  gen-like mixed cyclic oligomers containing furans, pyrroles and thiophenes have been synthesized by ‘3+1’, ‘3+2’ and ‘3+ketone’ approaches. Condensation of 2,5-bis[1-methyl-1(1H-pyrrol-2-yl)-ethyl]furan with 2,5-bis[(α-hydroxy-α,α-dimethyl)furan or 2,5-bis[(α-hydroxy-α,α-dimethyl)thiophene resulted in the formation of the mixture of cyclic tetramer, cyclic octamer and cyclic hexamer possessing different

  已通过“ 3 + 1”，“ 3 + 2”和“ 3+酮”方法合成了含有呋喃，吡咯和噻吩的内消旋-二烷基卟啉原样混合环状低聚物。2,5-双[1-甲基-1（1 H）的缩合-吡咯-2-基）-乙基]呋喃与2,5-双[（α-羟基-α，α-二甲基）呋喃或2,5-双[（α-羟基-α，α-二甲基）噻吩在形成具有不同数量的呋喃（噻吩）和吡咯的环状四聚体，环状八聚体和环状六聚体的混合物时。发现主要产物是“ 3 + 1”缩合中的环状四聚体，而环状五聚体是“ 3 + 2”缩合中的主要产物。在“ 3 + 2”缩合反应中分离出相当数量的环状十聚体。“ 3 + 1”缩合反应中呋喃-吡咯交替环状六聚体的形成表明反应过程中原料对酸的催化可逆裂解。同样，通过“ 4 + 2”方法合成了环十二酰胺。通过缩合2,5-双[1-甲基-1（1H-吡咯-2-基）-乙基]呋喃与酮。检查了催化剂，温度，模板，溶剂和浓度的影响，未发现产物分布有明显变化。
• Bis(tetrathiafulvalene)-Calix[2]pyrrole[2]- thiophene and Its Complexation with TCNQ
  作者：Thomas Poulsen、Kent A. Nielsen、Andrew D. Bond、Jan O. Jeppesen

  DOI：10.1021/ol7024235

  日期：2007.12.1

  The synthesis of a rare example of a calix[2]pyrrole[2]thiophene derivative incorporating two tetrathiafulvalene units is described along with its X-ray crystal structure. Complexation studies between the bis(tetrathiafulvalene)-calix[2]pyrrole[2]thiophene and 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) were carried out in solution using absorption and ESR spectroscopies as well as in the solid state

  描述了结合有两个四硫富瓦烯单元的杯[2]吡咯[2]噻吩衍生物的罕见实例的合成及其X射线晶体结构。在溶液中使用吸收光谱和ESR光谱对双（四硫富瓦烯）-杯[2]吡咯[2]噻吩和7,7,8,8-四氰基-对-喹二甲烷（TCNQ）之间的络合物进行了研究。使用X射线晶体学和IR光谱分析固态。
• Synthesis and Structure of Calix[n]bifurano[n]thiophene (n = 2-5) Hybrid Macrocycles
  作者：Seong-Jin Hong、Jae-Won Ka、Eun-Hee Jeoung、Chang-Hee Lee

  DOI：10.5012/bkcs.2011.32.8.3094

  日期：2011.8.20
• Synthesis of calix[n]furano[n]pyrroles and calix[n]thieno[n]pyrroles (n=2,3,4) by ‘3+1’ approach
  作者：Yong-Sung Jang、Han-Je Kim、Phil-Ho Lee、Chang-Hee Lee

  DOI：10.1016/s0040-4039(00)00294-x

  日期：2000.4

  Condensation of 5,5,10,10-tetramethyl-16-oxa-tripyrromethane and 2,5-bis[(alpha-hydroxy-alpha,alpha-dimethyl)methyl]furan or 2,5-bis[(alpha-hydroxy-alpha,alpha-dimethyl)methyl]thiophene resulted in cyclic, alternating oligomers of furan(thiophene) and pyrrole. The product distribution is independent of the reaction conditions, the presence of inorganic additives and temperature. (C) 2000 Elsevier Science Ltd. All rights reserved.
• <i>ansa</i>-Ferrocene-Incorporated Calixpyrroles and Calixphyrins: Syntheses and Spectral/Structural Characterization
  作者：S. Ramakrishnan、K. S. Anju、Ajesh P. Thomas、K. C. Gowri Sreedevi、P. S. Salini、M. G. Derry Holaday、Eringathodi Suresh、A. Srinivasan

  DOI：10.1021/om300004m

  日期：2012.6.11

  The syntheses and spectral/structural characterization of ansa-ferrocene-incorporated normal calixphyrins and core-modified calixpyrroles and calixphyrins are reported. Acid-promoted dehydrative condensation of 1,1'-bis-(dimethylpyrrolylmethyl)ferrocene and 2,5-bis(dimethylhydroxymethyl)thiophene/furan yielded ansa-ferrocene-based core-modified calixpyrroles, while acid-catalyzed dehydrative condensation of 1,1'-bis(diphenylpyrrolylmethyl)ferrocene with the aryl aldehydes and 2,5-bis(phenylhydroxymethyl)thiophene followed by DDQ oxidation resulted in the formation of ansa-ferrocene-appended normal and core-modified calixphyrins, respectively. The newly synthesized macrocycles were characterized by FAB-MS, NMR, and UV-vis spectral analyses and finally confirmed by single-crystal X-ray structural analysis. All these studies clearly revealed the introduction of ferrocene in the main framework of the corresponding macrocycles in an ansa-type way. The core-modified calixpyrroles adopt a 1,3-alternate conformation, while the corresponding calixphyrins maintained partial planarity along the tripyrrin plane due to the presence of meso sp(2) carbon and generated curved staircase conformation. In addition to the intramolecular hydrogen-bonding interactions, calixphyrins generate self-assembled dimers, one- and two-dimensional supramolecular assemblies through intermolecular hydrogen bonding in the solid state.