3-(苄基硫代)-4-氧代-4,5,6,7-四氢苯并[c]噻吩-1-羧酸乙酯 | 172516-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-(苄基硫代)-4-氧代-4,5,6,7-四氢苯并[c]噻吩-1-羧酸乙酯
• 英文名称: ethyl 3-(benzylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate
• 英文别名: BTH4；ethyl 3-benzylsulfanyl-4-oxo-6,7-dihydro-5H-2-benzothiophene-1-carboxylate
• CAS: 172516-35-7
• 化学式: C₁₈H₁₈O₃S₂
• mdl: MFCD00085055
• 分子量: 346.471
• InChiKey: HHGLCIVVJISXCA-UHFFFAOYSA-N

物化性质

• 沸点：
  537.7±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  96.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(苄基硫代)-4-氧代-4,5,6,7-四氢苯并[c]噻吩-1-羧酸乙酯 在 1,3-二氯-5,5-二甲基海因 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 以94 %的产率得到ethyl 3-(chlorosulfonyl)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate
  参考文献：
  名称：

  通过氧化氯化和Radical Smiles重排大规模合成宝石二氟取代的4,5,6,7-四氢苯并[c]噻吩-4-酮杂环

  摘要：

  我们报告了一种优化的合成路线，分 4 步合成带有偕二氟亚甲基部分的官能化 4,5,6,7-四氢苯并[ c ]噻吩杂环，总产率为 43%。CF 2片段使用构建块方法掺入，通过将适当的氟化醇与C-3磺酰氯偶联，C-3磺酰氯通过环外苄基硫醚的氧化氯化合成。然后，所得氟磺酸酯通过可见光介导的 Smiles 重排提供所需的氟化噻吩支架。

  DOI：

  10.1055/a-2153-7341
• 作为产物：
  描述：

  1,3-环己二酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 3-(苄基硫代)-4-氧代-4,5,6,7-四氢苯并[c]噻吩-1-羧酸乙酯
  参考文献：
  名称：

  通过氧化氯化和Radical Smiles重排大规模合成宝石二氟取代的4,5,6,7-四氢苯并[c]噻吩-4-酮杂环

  摘要：

  我们报告了一种优化的合成路线，分 4 步合成带有偕二氟亚甲基部分的官能化 4,5,6,7-四氢苯并[ c ]噻吩杂环，总产率为 43%。CF 2片段使用构建块方法掺入，通过将适当的氟化醇与C-3磺酰氯偶联，C-3磺酰氯通过环外苄基硫醚的氧化氯化合成。然后，所得氟磺酸酯通过可见光介导的 Smiles 重排提供所需的氟化噻吩支架。

  DOI：

  10.1055/a-2153-7341

文献信息

• Condensed 4,5,6,7-tetrahydrobenzo[C]thiopenes as enhancer for cell differentiation induction factor action
  申请人：——

  公开号：US20020049242A1

  公开（公告）日：2002-04-25

  A compound represented by the formula: 1 wherein X represents a sulfur atom or an oxygen atom; Y represents an optionally oxidized sulfur atom or an oxygen atom; Z represents a bond or a divalent hydrocarbon group; R 1 represents an optionally substituted hydrocarbon group; R 2 represents an optionally amidated or esterified carboxyl group; ring A represents an optionally substituted aromatic 5-membered heterocyclic ring; or a salt thereof. A compound of the above formula possesses cell differentiation inducing factor action-enhancing activity and anti-matrix metalloprotease activity and that is useful in the prevention and treatment of bone diseases such as osteoporosis, bone fractures, osteoarthritis and rheumatoid arthritis, arteriosclerosis, cancer metastasis, and diseases based on nerve degeneration.

  公式1所表示的化合物：其中X代表硫原子或氧原子；Y代表可选氧化的硫原子或氧原子；Z代表键或二价碳氢基团；R1代表可选取代的碳氢基团；R2代表可选酰胺化或酯化的羧基；环A代表可选取代的芳香性5-成员杂环；或其盐。上述公式的化合物具有细胞分化诱导因子增强活性和抗基质金属蛋白酶活性，可用于预防和治疗骨疾病，如骨质疏松症、骨折、骨关节炎和类风湿性关节炎、动脉硬化、癌症转移和基于神经退化的疾病。
• Methods and kits for the detection of endotoxi
  申请人：——

  公开号：US20020182641A1

  公开（公告）日：2002-12-05

  Methods for determining levels of endotoxin in a sample are provided. These methods are useful in the diagnosis of septicemia. Kits for the detection of endotoxin are also provided.

  提供了测定样本中内毒素水平的方法。这些方法可用于败血症的诊断。还提供了检测内毒素的试剂盒。
• Tetrahydrobenzothiophenone Derivatives as a Novel Class of Adenosine Receptor Antagonists
  作者：A. Michiel van Rhee、Suhaib M. Siddiqi、Neli Melman、Dan Shi、William L. Padgett、John W. Daly、Kenneth A. Jacobson

  DOI：10.1021/jm9504823

  日期：1996.1.1

  A novel class of non-nitrogen-containing heterocycles, the tetrahydrobenzothiophenones, was found to bind to adenosine receptors as antagonists in the micromolar range. Affinity was determined in radioligand-binding assays at rat brain A(1) and A(2a) receptors. A structure-activity analysis indicated that a 3-thioether group is favored and affinity at A(2a), but not at AL, receptors is highly dependent on this thioether substituent. A carboxylic acid-derived substituent is required at the 1-position of the thiophene ring, with esters being more potent in binding at A(1) receptors than the corresponding carboxyl hydrazide or carboxylic acid derivatives. The methyl (15) and ethyl (16) esters are about equipotent at A(1) but not at A(2a) receptors. A 4-keto group on the saturated ring is favored for receptor affinity. Dimethyl substitution at the B-position of the saturated ring is allowed. One of the most potent derivatives was the nonselective compound ethyl 3-(benzylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate (BTH4, 7; Figure 1), which antagonized adenosine agonist-induced inhibition of adenylyl cyclase in rat adipocyte membranes with a K-B value of 1.62 +/- 0.73 mu M and adenosine agonist-induced stimulation of adenylyl cyclase in pheochromocytoma cell membranes with a K-B value of 9.19 +/- 0.98 mu M. Displacement of radioligand binding by BTH4 (7) at cloned human A(3) receptors was negligible, but one slightly A(3) selective compound (11, 3.9-fold over A(1) and >7.5-fold over A(2a)) was found. A 1-methylpropyl thioether (17) was 29-fold selective for A(1) vs A(2a) receptors. BTH4 (7) alone, at 10 mg/kg, stimulated locomotor activity in mice but paradoxically acted, under certain circumstances, synergistically with an A(1) selective agonist to depress locomotor activity. A pharmacophore model relating structural features of xanthine and non-xanthine adenosine antagonists to BTH4 (7) suggests a high degree of similarity in electrostatic surfaces, assuming that the thiophene ring superimposes the region of the uracil ring of xanthines.
• METHODS AND KITS FOR THE DETECTION OF ENDOTOXIN
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：EP0906574B1

  公开（公告）日：2004-04-14
• CONDENSED 4,5,6,7-TETRAHYDROBENZO C]THIOPHENES AS ENHANCER FOR CELL DIFFERENTIATION INDUCTION FACTOR ACTION
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0931074B1

  公开（公告）日：2003-05-07