(1-benzothiophen-5-yl)acetonitrile | 17381-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (1-benzothiophen-5-yl)acetonitrile
• 英文别名: 2-(benzo[b]thiophen-5-yl)acetonitrile；benzo(b)thiophene-5-acetonitrile；benzo[b]thiophen-5-yl-acetonitrile；(Benzo[b]thiophen-5-yl)acetonitrile；2-(1-benzothiophen-5-yl)acetonitrile
• CAS: 17381-51-0
• 化学式: C₁₀H₇NS
• 分子量: 173.238
• InChiKey: KCINAEFQFUWUIB-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  110-112 °C(Press: 3 Torr)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-benzothiophen-5-yl)acetonitrile 在 氢氧化钾 、 硼烷四氢呋喃络合物 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-(2-羟基乙基)苯并[b]噻吩
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m
• 作为产物：
  描述：

  5-溴苯并[b]噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 水 、 caesium carbonate 、 sodium chloride 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 生成 (1-benzothiophen-5-yl)acetonitrile
  参考文献：
  名称：

  [EN] ADVANTAGEOUS BENZOTHIOPHENE COMPOSITIONS FOR MENTAL DISORDERS OR ENHANCEMENT
  [FR] COMPOSITIONS DE BENZOTHIOPHÈNE AVANTAGEUSES POUR TROUBLES MENTAUX OU AMÉLIORATION MENTALE

  摘要：

  具有药用活性的苯并噻吩化合物及其药用可接受的盐和盐混合物，以及用于治疗精神障碍或精神增强的药用可接受的组合物，包括用于接触素疗法，通常用于调节中枢神经系统活动。

  公开号：

  WO2022010937A1

文献信息

• Pyrazole glucokinase activators
  申请人：Berthel Steven Joseph

  公开号：US20080021032A1

  公开（公告）日：2008-01-24

  Disclosed herein are pyrazole glucokinase activators of the formula (I) useful for the treatment of metabolic diseases and disorders, preferably diabetes mellitus.

  本文披露了一种式(I)的吡唑葡萄糖激酶激活剂，用于治疗代谢性疾病和紊乱，最好是糖尿病。
• Assembly of α‐(Hetero)aryl Nitriles via Copper‐Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
  作者：Ying Chen、Lanting Xu、Yongwen Jiang、Dawei Ma

  DOI：10.1002/anie.202014638

  日期：2021.3.22

  conditions, affording α‐(hetero)arylacetonitriles via one‐pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α‐alkyl‐substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α‐alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities

  α-（杂）芳基腈是药物设计的重要结构图案。通过与（杂）芳基卤化物偶合直接合成这些化合物的已知方法具有狭窄的反应范围。本文中，我们报道铜盐和草酸二酰胺的结合能够在温和的条件下偶联多种（杂）芳基卤化物（Cl，Br）和氰基乙酸乙酯，从而通过一锅脱羧作用提供α-（杂）芳基乙腈。此外，（杂）芳基溴化物与α-烷基取代的氰基乙酸乙酯的CuBr /草酸二酰胺催化偶合在60°C下平稳进行，导致脱羧后形成α-烷基（杂）芳基乙腈。该方法具有一般的底物范围，并且与各种功能和杂芳基相容。
• METHOD FOR PRODUCING 5-(BROMOMETHYL)-1-BENZOTHIOPHENE
  申请人：FUJIFILM TOYAMA CHEMICAL CO., LTD

  公开号：US20190119242A1

  公开（公告）日：2019-04-25

  Provided is a method for industrially producing 5-(bromomethyl)-1-benzothiophene. The production method according to the present invention comprises: (1) a step for introducing 5-methyl-1-benzothiophene, a brominating agent, and a solvent into a reactor; (2) a step for emitting light having a wavelength range of 200-780 nm inside the reactor; and (3) a step for recovering 5-(bromomethyl)-1-benzothiophene from the reactor.

  提供了一种工业生产5-(溴甲基)-1-苯并噻吩的方法。根据本发明的生产方法包括：(1)将5-甲基-1-苯并噻吩、溴化剂和溶剂引入反应器的步骤；(2)在反应器内发射波长范围为200-780纳米的光的步骤；和(3)从反应器中回收5-(溴甲基)-1-苯并噻吩的步骤。
• Benzofuran acetic acid esters and their arthropocidal compositions
  申请人：Shell Internationale Research Maatschappij B.V.

  公开号：US04372970A1

  公开（公告）日：1983-02-08

  There are provided benzofuran-substituted acetic acid esters and compositions thereof having arthropocidal activity.

  提供了含苯并呋喃取代的乙酸酯及其具有杀虫活性的组合物。
• PROCESS FOR PRODUCTION OF 1-(3-(2-(1-BENZOTHIOPHEN-5-YL)-ETHOXY)PROPYL)AZETIDIN-3-OL OR SALTS THEREOF
  申请人：Saitoh Akihito

  公开号：US20090069576A1

  公开（公告）日：2009-03-12

  A Process for production of 1-(3-(2-(1-benzothiophen-5-yl)ethoxy)propyl)azetidin-3-ol or salts thereof which comprises using as a starting compound as a (phenylthio)acetic acid derivative or salts thereof represented by the general formula: wherein X 1 represents a halogen atom, is useful as a safe process for mass production of 1-(3-(2-(1-benzothiophen-5-yl)ethoxy)propyl)azetidin-3-ol or salts thereof which is useful as a remedy for disease of central and peripheral nerve.

  一种生产1-(3-(2-(1-苯并噻吩-5-基)乙氧基)丙基)氮杂环己烷-3-醇或其盐的工艺，其中使用作为起始化合物的(苯硫)乙酸衍生物或其盐，其通式表示为：其中X1表示卤素原子，此工艺适用于安全地大规模生产1-(3-(2-(1-苯并噻吩-5-基)乙氧基)丙基)氮杂环己烷-3-醇或其盐，该化合物可用于治疗中枢和周围神经疾病。