phenylbis(3-thienyl)carbinol | 133373-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylbis(3-thienyl)carbinol
• 英文别名: phenylbis(3-thienyl)methanol；Phenyl-di(thiophen-3-yl)methanol
• CAS: 133373-90-7
• 化学式: C₁₅H₁₂OS₂
• 分子量: 272.392
• InChiKey: HBRMMKZQMYEYFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenylbis(3-thienyl)carbinol 在 硫酸 作用下， 生成 3-[phenyl(thiophen-1-ium-3-ylidene)methyl]thiophene
  参考文献：
  名称：

  The tris(2-thienyl)methyl cation problem. NMR spectroscopic study

  摘要：

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.

  DOI：

  10.1021/jo00010a011
• 作为产物：
  描述：

  3-thienyl lithium 、 苯甲酸甲酯 以 乙醚 为溶剂， 以66%的产率得到phenylbis(3-thienyl)carbinol
  参考文献：
  名称：

  The tris(2-thienyl)methyl cation problem. NMR spectroscopic study

  摘要：

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.

  DOI：

  10.1021/jo00010a011

文献信息

• Syntheses, Crystal Structures, and Physico-Chemical Studies of Sodium and Potassium Alcoholates Bearing Thienyl Substituents and their Derived Luminescent Samarium(III) Alkoxides
  作者：Michael Veith、Céline Belot、Volker Huch、Laurent Guyard、Michael Knorr、Abderrahim Khatyr、Claudia Wickleder

  DOI：10.1002/zaac.201000205

  日期：2010.9

  The synthesis, structural characterisation, electrochemistry, and luminescence properties of a series of alkali metal alcoholates and samarium(III) alkoxides with thiophene-based OR substituents are presented. The alkali metal alcoholates 7–15 were obtained by deprotonation of the carbinol with NaH or KH. Their molecular structures consist of tetranuclear alkali metal alcoholates with a distorted cubane-like

  介绍了一系列具有噻吩基 OR 取代基的碱金属醇化物和钐 (III) 醇盐的合成、结构表征、电化学和发光特性。碱金属醇化物 7-15 是通过甲醇与 NaH 或 KH 的去质子化获得的。它们的分子结构由四核碱金属醇化物和扭曲的立方烷状 M4O4 核心组成（X 射线结构分析）。每个碱金属都被三个羧酸盐配体和（取决于衍生物）额外的四氢呋喃分子包围。通过盐复分解合成了单核钐醇盐Sm[OC(C4H3S)3]3(thf)3}·thf(16)和Sm[OC(C16H13S)]3(thf)3}·thf(17) [KOC(C4H3S)3]4(thf)2}·thf(7)、[NaOC(C4H3S)3]4(thf)2(8)或[KOC(C16H13S)]4(thf)3之间的反应}·1/2thf (11), 分别为 thf 溶液中的 SmCl3。这些对空气敏感的碱加合物的分子结构已通过单晶 X 射线晶体学确定，并
• New Yttrium and Europium(+3) Alkoxides Bearing Thiophene Units: Syntheses, Crystal Structure Determinations and Physico‐Chemical Properties
  作者：Michael Veith、Céline Belot、Volker Huch

  DOI：10.1002/ejic.201101089

  日期：2012.3

  spectroscopy. In addition, a novel europium(+3) alkoxide Eu[OC(C4H3S)3]3(thf)3}·thf (15) was synthesized by the reaction between Eu[N(SiMe3)2]3 and the tertiary alcohol HO–C(C4H3S)3 (1) in thf. The molecular structure of this compound reveals an approximately octahedral coordination sphere around the europium(+3) metal centre with three methoxido ligands and three facially arranged tetrahydrofuran molecules

  介绍了一系列带有噻吩部分的新型钇和铕 (+3) 醇盐的合成、结构表征、电化学和发光特性。钇化合物是通过 Y[N(SiMe3)2]3 与叔醇 HO–C(C16H13S) (2)、HO–C(C17H15S) (3)、HO–C(C14H11S2) (4) 之间的反应获得的) 和 HO–C(C16H13S) (5) 在 thf 或甲苯和吡啶的混合物中。X 射线晶体衍射测量显示了一个五配位的钇原子在扭曲的三角双锥几何中。金属中心被赤道位置的三甲氧基配体和两个四氢呋喃 [for Y[OC(C16H13S)]3(thf)2}·甲苯 (8), Y[OC(C17H15S)]3(thf)2}·甲苯(10)和Y[OC(C14H11S2)]3(thf)2}·1/2甲苯(12)]或两个吡啶[对于Y [OC(C16H13S)]3(py)2}·甲苯(9)和Y[OC(C17H15S)]3(py)2}·甲苯(11
• The tris(2-thienyl)methyl cation problem. NMR spectroscopic study
  作者：Belen Abarca、Gregorio Asensio、Rafael Ballesteros、Teresa Varea

  DOI：10.1021/jo00010a011

  日期：1991.5

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.