diphenyl(2-thienyl)methanol | 79654-37-8

• 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: diphenyl(2-thienyl)methanol
• 英文别名: diphenyl-2-thienylcarbinol；(2-thienyl)diphenylcarbinol；diphenyl(thiophen-2-yl)methanol；NSC 241129
• CAS: 79654-37-8
• 化学式: C₁₇H₁₄OS
• 分子量: 266.364
• InChiKey: FKPBWSNNHLBCQG-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C(Solv: ligroine (8032-32-4))
• 沸点：
  421.6±40.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diphenyl(2-thienyl)methanol 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以94%的产率得到2-二苯甲基噻吩
  参考文献：
  名称：

  Reduction of tri(hetero)arylcarbinols to tri(hetero)arylmethanes

  摘要：

  DOI：

  10.1007/bf00809768
• 作为产物：
  描述：

  三苯基甲醇 在 palladium diacetate 、 caesium carbonate 、 三环己基膦 作用下， 以 邻二甲苯 为溶剂， 生成 diphenyl(2-thienyl)methanol
  参考文献：
  名称：

  钯催化的α，α-二取代的芳基甲醇的芳基化反应，是通过CC或CH键的裂解来实现的。

  摘要：

  钯催化的α，α-二取代的芳基甲醇与芳基卤化物的芳基化反应不仅通过邻位的CH键裂解，还通过sp（2）-sp（3）CC键的裂解以及酮的释放而进行（β-碳消除）得到相应的联芳基。这两个反应似乎都是通过常见的芳基钯（II）醇盐中间体发生的。报道了关于在芳基化中优先裂解CC或CH键的系统研究的结果。在重要发现中，由于空间原因，甚至可以从芳基（二苯基）甲醇中选择性除去邻位取代的芳基。因此，通过用芳基溴化物和氯化物处理相应的芳基（二苯基或二甲基）甲醇，可以有效地生产具有邻取代基的各种联芳基。

  DOI：

  10.1021/jo0344034

文献信息

• Iron-catalysed 1,2-aryl migration of tertiary azides
  作者：Kaijie Wei、Tonghao Yang、Qing Chen、Siyu Liang、Wei Yu

  DOI：10.1039/d0cc04579a

  日期：——

  1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

  通过使用FeCl 2 / N-杂环卡宾（NHC）SIPr·HCl催化体系，实现了α，α-二芳基叔叠氮化物的1,2-芳基迁移。一锅降低迁移结果亚胺后，该反应以高收率生成苯胺产物。
• Radical-promoted site-specific cross dehydrogenative coupling of heterocycles with nitriles
  作者：Zhong-Quan Liu、Zejiang Li

  DOI：10.1039/c6cc08213k

  日期：——

  A first free-radical triggered site-specific cross dehydrogenative coupling reaction of heterocycles with simple nitriles is developed. It allows efficient and facile access to various C-2 cyanoalkylated furans, thiophenes, indoles, and pyrroles. The extremely high selectivities in this case indicate that functionalization of an inert C–H bond could be well-controlled by radical initiation.

  开发了一种首次由自由基触发的异环化合物与简单腈发生特定位点的脱氢交叉偶联反应。它能够有效且便捷地获得各种C-2氰基烷基化的呋喃、噻吩、吲哚和吡咯。在这种情况下极高的选择性表明，通过自由基引发可以很好地控制惰性C-H键的官能化。
• Hydrogen bonding in diphenylmethanols, <i>R</i>CPh₂OH: structures of monomeric (4-biphenyl)diphenylmethanol and diphenyl(2-pyridyl)methanol, dimeric 1,1,3-triphenylpropyn-1-ol, trimeric 2-methyl-1,1-diphenylpropan-1-ol, tetrameric diphenyl(2-thienyl)methanol, hexameric bis(pentafluorophenyl)methanol (at 293 and 173 K) and polymeric diphenylmethanol
  作者：G. Ferguson、C. D. Carroll、C. Glidewell、C. M. Zakaria、A. J. Lough

  DOI：10.1107/s0108768194013984

  日期：1995.6.1

  (4-Biphenyl)diphenylmethanol (1), C25H20O, orthorhombic, P2(1)2(1)2(1), a = 8.3580 (11), b = 13.8976 (17), c = 15.5915 (12)Angstrom, Z = 4, R = 0.032 for 1146 observations [I > 3 sigma(I)]: the structure contains isolated monomers with no hydrogen bonding. Diphenyl(2-pyridyl)methanol (2), C18H15NO, monoclinic, P2(1)/c, a = 8.1899 (8), b = 14.855 (2), c = 11.6069 (15)Angstrom, beta = 96.344 (8)degrees, Z = 4, R = 0.049 for 879 observations [I > 3 sigma(1)]: the structure consists of isolated monomers in which the intramolecular O-H ... N hydrogen-bond motif has graph set S(5). 1,1,3-Triphenylpropyn-1-ol (3), C21H16O, monoclinic, P2(1)/c, a = 5.9794 (12), b = 9.953 (3), c = 26.420 (3)Angstrom, beta = 91.365 (12)degrees, Z = 4, R = 0.039 for 971 observations [I > 2 sigma(I)]: the structure contains centrosymmetric dimers held together by O-H ...pi(arene) hydrogen bonds involving one of the phenyl groups, rather than the propargyl group. 2-Methyl-1,1-diphenylpropan-1-ol (4), C16H18O, trigonal, P31c, a = 13.9232 (17), c = 12.0200 (19)Angstrom, Z = 6, R = 0.031 for 763 observations [I > 3 sigma(I)]: the structure consists of cyclic hydrogen-bonded trimers with crystallographic threefold symmetry and disordered hydroxyl H atoms in a motif with graph set R(3)(3)(6): the O ... O distance in the trimers is 2.864 (7)Angstrom. Diphenyl(2-thienyl)methanol (5), C17H14OS, rhombohedral, R $($) over bar$$ 3, a = 19.20 (1), c = 26.48 (1)Angstrom, Z = 24: this compound is isomorphous and isostructural with triphenylmethanol, Ph,COH, and forms hydrogen-bonded tetrahedral tetramers. Bis(pentafluorophenyl)methanol (6), C13H2F10O, rhombohedral, R $($) over bar$$ 3, a = 26.113 (3), c = 9.788 (3)Angstrom (at 293 K), R = 0.068 for 1214 observations [I > 2 sigma(I)]; a = 26.006 (4), c = 9.5941 (11)Angstrom (at 173 K), R = 0.072 for 1889 observations [I > 2 sigma(I)], Z = 18; the structure consists of coaxial stacks of cyclic hydrogen-bonded hexamers, each of ($) over bar 3 symmetry, and with a hydrogen-bond motif of graph set R(6)(6)(12). Within the hexamers, the molecules are disordered over two orientations in the ratio 0.779 (3):0.221 (3) at 293 K and 0.776 (2):0.224 (2) at 173 K: the O ... O distance is 2.702 (4)Angstrom at 293 K and 2.683 (4)Angstrom at 173 K. Diphenylmethanol (7), C13H12O, orthorhombic, P22(1)2(1), a = 5.1300 (10), b = 18.650 (5), c = 21.168 (6)Angstrom, Z = 8, R = 0.035 for 1487 observations [I > 3 sigma(I)]: there are two molecules in the asymmetric unit and the molecules are linked by hydrogen bonds into spiral chains having graph set C(4) and lying parallel to the a-axis; the O ... O distances within the chains are 2.826 (3) and 2.878 (3)Angstrom.

  (4-联苯基)二苯基甲醇(1)，化学式为C25H20O，属于正交晶系，空间群为P2(1)2(1)2(1)，晶胞参数为a = 8.3580(11) Å，b = 13.8976(17) Å，c = 15.5915(12) Å，单位晶胞分子数Z = 4。该晶体结构由孤立的单体分子组成，不存在氢键，R因子为0.032，基于1146次观测数据（I > 3σ(I)）。 二苯基(2-吡啶基)甲醇(2)，化学式为C18H15NO，属于单斜晶系，空间群为P2(1)/c，晶胞参数为a = 8.1899(8) Å，b = 14.855(2) Å，c = 11.6069(15) Å，β角为96.344(8)°，单位晶胞分子数Z = 4。该结构由孤立单体组成，分子内存在O-H...N氢键，图式集为S(5)，R因子为0.049，基于879次观测数据（I > 3σ(I)）。 1,1,3-三苯基丙炔-1-醇(3)，化学式为C21H16O，属于单斜晶系，空间群为P2(1)/c，晶胞参数为a = 5.9794(12) Å，b = 9.953(3) Å，c = 26.420(3) Å，β角为91.365(12)°，单位晶胞分子数Z = 4。该结构由中心对称的二聚体组成，通过O-H...π(芳环)氢键连接，其中一个苯基参与氢键而非丙炔基，R因子为0.039，基于971次观测数据（I > 2σ(I)）。 2-甲基-1,1-二苯基丙-1-醇(4)，化学式为C16H18O，属于三斜晶系，空间群为P31c，晶胞参数为a = 13.9232(17) Å，c = 12.0200(19) Å，单位晶胞分子数Z = 6。该结构由具有晶体学三重对称性的环状氢键三聚体组成，羟基H原子在图式集R(3)(3)(6)中处于无序状态，三聚体中O...O距离为2.864(7) Å，R因子为0.031，基于763次观测数据（I > 3σ(I)）。 二苯基(2-噻吩基)甲醇(5)，化学式为C17H14OS，属于菱形晶系，空间群为R$\bar3}$，晶胞参数a = 19.20(1) Å，c = 26.48(1) Å，单位晶胞分子数Z = 24。该化合物与三苯基甲醇结构和晶形相同，形成通过氢键连接的四面体四聚体。 双(五氟苯基)甲醇(6)，化学式为C13H2F10O，属于菱形晶系，空间群为R$\bar3}$，晶胞参数在293 K时为a = 26.113(3) Å，c = 9.788(3) Å，R因子为0.068，基于1214次观测数据（I > 2σ(I)）；在173 K时为a = 26.006(4) Å，c = 9.5941(11) Å，R因子为0.072，基于1889次观测数据（I > 2σ(I)），单位晶胞分子数Z = 18。该结构由具有$\bar3}$对称性的环状氢键六聚体堆叠而成，每个六聚体内分子在两种取向下无序，293 K时比例为0.779(3):0.221(3)，173 K时为0.776(2):0.224(2)。六聚体内O...O距离分别为293 K时的2.702(4) Å和173 K时的2.683(4) Å。 二苯基甲醇(7)，化学式为C13H12O，属于正交晶系，空间群为P22(1)2(1)，晶胞参数为a = 5.1300(10) Å，b = 18.650(5) Å，c = 21.168(6) Å，单位晶胞分子数Z = 8。该结构中两个分子在不对称单元中由氢键连接形成沿a轴螺旋的链状结构，图式集为C(4)。链内O...O距离分别为2.826(3) Å和2.878(3) Å，R因子为0.035，基于1487次观测数据（I > 3σ(I)）。
• 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
• Palladium-catalyzed direct oxidative vinylation of thiophenes and furans under weakly basic conditions
  作者：Atsushi Maehara、Tetsuya Satoh、Masahiro Miura

  DOI：10.1016/j.tet.2008.01.058

  日期：2008.6

  The palladium-catalyzed oxidative coupling of thiophenes and furans with alkenes proceeds in the presence of copper and lithium salts as oxidant and additive, respectively, under weakly basic or almost neutral conditions to afford the corresponding vinylated heteroarenes. Under such conditions, diphenyl(hydroxy)methyl and acetal functions on the heteroarene substrates are tolerable. The former function

  在弱碱性或几乎中性的条件下，分别在铜盐和锂盐作为氧化剂和添加剂的情况下，噻吩和呋喃与烯烃的钯催化氧化偶联进行，从而得到相应的乙烯基化杂芳烃。在这样的条件下，杂芳烃底物上的二苯基（羟基）甲基和乙缩醛功能是可以容忍的。噻吩环上的前一个官能团可以在乙烯基化后通过C-C键断裂被钯催化的芳基化反应取代，从而生成2-芳基-5-乙烯基噻吩。