2,3-双(溴甲基)-1-苯并噻吩 | 99074-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2,3-双(溴甲基)-1-苯并噻吩
• 英文名称: 2,3-Bis(bromomethyl)benzothiophene
• 英文别名: 2,3-Bis(brommethyl)benzothiophen；2,3-bis-bromomethyl-benzo[b]thiophene；2,3-Bis-brommethyl-benzo[b]thiophen；Benzo[b]thiophene, 2,3-bis(bromomethyl)-；2,3-bis(bromomethyl)-1-benzothiophene
• CAS: 99074-13-2
• 化学式: C₁₀H₈Br₂S
• 分子量: 320.048
• InChiKey: DTBQRHSJVOFWJB-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  379.9±32.0 °C(Predicted)
• 密度：
  1.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-双(溴甲基)-1-苯并噻吩 在 氢氧化钾 、 氧气 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 Anthra<2,3-b>benzothiophen-7,12-dion
  参考文献：
  名称：

  Dyker, Gerald; Kreher, Richard P., Chemische Berichte, 1988, vol. 121, p. 1203 - 1206

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-bis-chloromethyl-benzo[b]thiophene 在 氢氧化钾 、 乙醚 、 potassium acetate 、 三溴化磷 、 溶剂黄146 作用下， 生成 2,3-双(溴甲基)-1-苯并噻吩
  参考文献：
  名称：

  Ried; Grabosch, Chemische Berichte, 1958, vol. 91, p. 2485,2495

  摘要：

  DOI：

文献信息

• IDO/TDO Inhibitor
  申请人：GENERAL INCORPORATED ASSOCIATION PHARMA VALLEY PROJECT SUPPORTING ORGANIZATION

  公开号：US20200239452A1

  公开（公告）日：2020-07-30

  A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, an aliphatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, an aliphatic ring and a heterocyclic ring; X, R 1 and R 2 represent a substituent on a ring atom constituting ring A; m represents an integer of 0 to 6; X represents, for example, a halogen atom; and R 1 and R 2 are the same or different and are selected from, for example, the group consisting of groups of formula (a) or formula (b); and in the following formula (a) and formula (b), Y is selected from the group consisting of O, S, and Se, Z is selected from the group consisting of O, S, and Se, n represents an integer of 1 to 8, r represents an integer of 1 to 8, s represents an integer of 1 to 8, R 4 represents, for example, —C(═NH)—HN 2 , and R 6 represents, for example, a substituted or unsubstituted aryl group].

  以下公式（I）给出的化合物或该化合物的药学上可接受的盐可用作IDO/TDO抑制剂。因此，公式（I）的化合物或该化合物的药学上可接受的盐可用作，例如，用于肿瘤、传染病、神经退行性疾病、白内障、器官移植排斥、自身免疫疾病、术后认知障碍以及与女性生殖健康相关的疾病的治疗剂。在以下公式（I）中，环A代表芳香环、脂环、杂环或两个或更多个选自芳香环、脂环和杂环的缩合环的环；X、R1和R2代表构成环A的环原子上的取代基；m代表0到6的整数；X代表例如卤素原子；R1和R2相同或不同，选自例如由公式（a）或公式（b）组成的基团，而在以下公式（a）和公式（b）中，Y选自O、S和Se组成的基团，Z选自O、S和Se组成的基团，n表示1到8的整数，r表示1到8的整数，s表示1到8的整数，R4代表例如—C(═NH)—HN2，R6代表例如取代或未取代的芳基。
• Lewis-Acid-Mediated Domino Reactions of Bis(diacetoxymethyl)-Substituted Arenes and Heteroarenes
  作者：J. Arul Clement、Ramakrishnan Sivasakthikumaran、Arasambattu K. Mohanakrishnan、S. Sundaramoorthy、Devadasan Velmurugan

  DOI：10.1002/ejoc.201001174

  日期：2011.1

  A one-pot synthesis of annulated heterocycles involving a Lewis-acid-mediated domino reaction of bis(diacetoxymethyl)-substituted arenes and heteroarenes is described. The reaction of the tetraacetates with arenes and heteroarenes leads to the formation of 1,1-bis-arylated diacetates upon elimination followed by electrocyclohetero-arylated intermediate may lead to the formation of bis-arylated 1,1-diacetates

  描述了涉及双（二乙酰氧基甲基）取代的芳烃和杂芳烃的路易斯酸介导的多米诺反应的环状杂环的一锅合成。四乙酸酯与芳烃和杂芳烃的反应导致在消除后形成 1,1-双芳基化二乙酸酯，然后是电环杂芳基化中间体可能导致形成双芳基化 1,1-二乙酸酯，其在环化后芳构化提供环状杂环。
• Facile Preparation of Indolyl-2/3-methylsulfoxides Using HF/H₂O₂
  作者：Ganesan Gobi Rajeshwaran、Neelamegam Ramesh、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397910802517848

  日期：2009.3.10

  A variety of indolyl-2/3-methylsulfides tethered with sensitive functionalities were oxidized to the corresponding sulfoxides using a hitherto unexplored HF/H2O2 system.
• Lewis Acid-Mediated Michaelis−Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
  作者：Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Radhakrishnan Sureshbabu、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol1029436

  日期：2011.3.18

  A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.
• Novel furan-, thiophene- and benzo[b]thiophene bridged macrocycles of 4,4′-bipyridine
  作者：Holger Scheytza、Hans-Ulrich Reissig、Otto Rademacher

  DOI：10.1016/s0040-4020(99)00144-1

  日期：1999.4

  Eight novel heterocyclic bridged phanes of the paraquat type were synthesized by a simple two-step procedure. Starting from furan bridged bis(4,4 '-bipyridinium) dication 2 and the corresponding bis(bromomethyl)arenes furanophanes of 4,4 '-bipyridine were obtained in moderate to high yields. In similar manner thiophenophane 9 was synthesized in low yield using dication 8 as precursor. The spectroscopic properties of furanophane 4 and thiophenophane 9 were compared. Cycloadditions on the furan ring failed, which is attributed to the decrease of electron density of the furan ring caused by neighbouring electron-accepting bipyridinium groups. The syntheses of the benzo[b]thiophene bridged phanes were performed starting from dibromide 10 and bis(4,4 '-bipyridinium) dications 12-14 since the instability of the required bis(4,4 '-bipyridinium) dication 11 did not allow its use in aqueous solution. (C) 1999 Elsevier Science Ltd. All rights reserved.