2-[α-(4-bromophenyl)-α-hydroxymethyl]thiophene | 40310-36-9

• 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: 2-[α-(4-bromophenyl)-α-hydroxymethyl]thiophene
• 英文别名: 2-(α-p-bromophenyl-α-hydroxymethyl)thiophene；(4-bromophenyl)-thiophen-2-yl-methanol；(4-bromophenyl)-thiophen-2-ylmethanol
• CAS: 40310-36-9
• 化学式: C₁₁H₉BrOS
• 分子量: 269.162
• InChiKey: UFRLLNUJMHVVMO-UHFFFAOYSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  397.7±32.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2-[α-(4-bromophenyl)-α-hydroxymethyl]thiophene 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到(4-溴苯基)-2-噻吩-甲酮
  参考文献：
  名称：

  [EN] NEW TRICYCLIC ANGIOTENSIN II AGONISTS
  [FR] NOUVEAUX AGONISTES TRICYCLIQUES DE L'ANGIOTENSINE II

  摘要：

  提供了式(I)的化合物，其中虚线，X1，X2，X3，X4，A，Y1，Y2，Y3，Y4，Z1，Z2，R2和R3的含义如描述中所给，并且其药学上可接受的盐，这些化合物可用作AT2受体的选择性激动剂，因此，特别适用于治疗包括消化不良、肠易激综合征和多器官功能衰竭在内的胃肠道疾病以及心血管疾病。

  公开号：

  WO2004046141A1
• 作为产物：
  描述：

  噻吩 、 对溴苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到2-[α-(4-bromophenyl)-α-hydroxymethyl]thiophene
  参考文献：
  名称：

  Synthesis of Functionalized Unsymmetrical Thiophene Diols and Their Use in the Synthesis ofcis-21-Monothia- andcis-21,23-Dithiaporphyrin Building Blocks with Two Different Functional Groups

  摘要：

  一系列功能化的非对称噻吩二醇被合成出来，并被用于合成具有两个不同官能团的中位点的顺式-21-单硫杂和顺式-21,23-二硫杂卟啉结构单元。为了展示具有两个不同官能团的顺式噻啉结构单元的使用，使用共价和非共价相互作用合成了由N4、N3S和N2S2卟啉亚基组成的卟啉三聚体。

  DOI：

  10.1055/s-2005-872245

文献信息

• Tritylium assisted iodine catalysis for the synthesis of unsymmetrical triarylmethanes
  作者：Thibaut Courant、Marine Lombard、Dina V. Boyarskaya、Luc Neuville、Géraldine Masson

  DOI：10.1039/d0ob01502d

  日期：——

  The combined Lewis acid catalytic system, generated from molecular iodine and tritylium tetrafluoroborate effectively catalyzed the Friedel–Crafts (FC) arylation of diarylmethyl sulfides providing an efficient access to various unsymmetrical triarylmethanes. The addition of tritylium and iodine created a more active catalytic system to promote the cleavage of sulfidic C–S bonds.

  由分子碘和四氟硼酸三苯甲基酯生成的组合路易斯酸催化体系有效地催化二芳基甲基硫醚的傅克（FC）芳基化，从而有效地获得各种不对称三芳基甲烷。三苯甲基和碘的添加创造了一个更活跃的催化体系，以促进硫化 C-S 键的断裂。
• One-Flask Synthesis of Mono- and Trifunctionalized 21-Thia and 21-Oxaporphyrin Building Blocks and Their Application in the Synthesis of Covalent and Noncovalent Unsymmetrical Porphyrin Arrays
  作者：Iti Gupta、Mangalampalli Ravikanth

  DOI：10.1021/jo040178u

  日期：2004.10.1

  symmetrical phenylethyne bridged dimer containing two N3S cores. A preliminary photophysical study on these dimers indicated a possibility of energy transfer from one subunit to another. We also demonstrated the use of trifunctionalized porphyrins in the synthesis of two noncovalent unsymmetrical porphyrin tetramers containing one N3S and three N4 porphyrin subunits.

  已开发出一种快速合成路线，可使用简单的前体例如2 [α-（芳基）-α-羟甲基]噻吩（噻吩单醇）和2 [α- （芳基）-α-羟甲基]呋喃（呋喃单醇）。在卟啉形成条件下，将一当量的噻吩或呋喃一元醇与两当量的芳基醛和三当量的吡咯缩合，然后进行柱色谱分离，得到官能化的21-硫杂或21-氧杂卟啉。为了合成单官能化的卟啉，使用了含有官能化的芳基的单醇。官能化的醛用于合成三官能化的卟啉。一元醇方法用途广泛，可用于合成含有官能团（如碘苯基，乙炔基苯基，羟苯基，溴苯基和吡啶基）的单官能和三官能化的21-硫杂和21-氧杂卟啉。含碘苯基和乙炔基苯基的单官能化卟啉结构单元进一步用于合成四个不对称的共价卟啉二聚体，其中包含两个不同的卟啉核心，例如N经由二芳基乙炔基桥接的3 S N 4，N 3 O-N 4和N 3 S-N 3 O和包含两个N 3 S核的一个对称的苯基乙炔桥接的二聚体。对这些二聚体的初步光物理研究表明，
• Novel and Rapid Synthetic Routes to A3B- and AB3-Type 21-Thiaporphyrins and Their Use in the Construction of Unsymmetrical Covalent and Non-Covalent Porphyrin Arrays
  作者：Iti Gupta、Neeraj Agarwal、Mangalampalli Ravikanth

  DOI：10.1002/ejoc.200300764

  日期：2004.4

  Novel and very simple methods were developed for the synthesis of 21-thiaporphyrins having both one functional group (A3B) and three functional groups (AB3). These A3B- and AB3-type 21-thiaporphyrin building blocks were used to synthesize both covalently and non-covalently linked unsymmetrical porphyrin arrays containing N3S and N4 porphyrin cores. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  开发了新颖且非常简单的方法来合成具有一个官能团 (A3B) 和三个官能团 (AB3) 的 21-硫卟啉。这些 A3B 和 AB3 型 21-硫卟啉构建块用于合成包含 N3S 和 N4 卟啉核心的共价和非共价连接的不对称卟啉阵列。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition
  作者：A.K. Mahalingam、Yiqian Wan、A.M.S. Murugaiah、Charlotta Wallinder、Xiongyu Wu、Bianca Plouffe、Milad Botros、Fred Nyberg、Anders Hallberg、Nicole Gallo-Payet

  DOI：10.1016/j.bmc.2010.03.064

  日期：2010.6.15

  Structural alterations to the benzylic position of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed, with the emphasis to reduce the CYP 450 inhibitory property of the initial structure. The imidazole moiety, responsible for the CYP 450 inhibitory effect in 1, was replaced with various heterocycles. In addition, the modes of attachment of the heterocycles, that is, carbon versus nitrogen attachment, and introduction of carbonyl functionalities to the benzylic position have been evaluated. In all the three series, AT(2) receptor ligands with affinity in the lower nanomolar range were identified. None of the analogues, regardless of the substituents, exhibited any affinity for the AT(1) receptor. Compounds with substantially reduced inhibition of the CYP 450 enzymes were obtained. Among them the compound 60 was found to induce neurite elongation in NG 108-15 cells and served as potent AT(2) selective agonist. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective addition of thiophenylboronic acids to aldehydes using ZnEt2/Schiff-base catalytic system
  作者：Xiaodong Liu、Li Qiu、Liang Hong、Wenjing Yan、Rui Wang

  DOI：10.1016/j.tetasy.2009.02.059

  日期：2009.3

  Using Schiff-base amino alcohols as catalysts which were readily derived from natural amino acids in three steps, a series of valuable optically active thiophenyl methanols (4a-4n) were first obtained in good yields and high enantioselectivities (up to 96% ee) through the asymmetric addition of thiophenylboronic acid to aldehydes in the presence of ZnEt2 in toluene. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.