3-氯噻吩-2-羧酸乙酯 | 153562-66-4

• 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-氯噻吩-2-羧酸乙酯
• 英文名称: ethyl 3-chlorothiophene-2-carboxylate
• CAS: 153562-66-4
• 化学式: C₇H₇ClO₂S
• 分子量: 190.65
• InChiKey: BLQUEYLSBBYPKM-UHFFFAOYSA-N

物化性质

• 沸点：
  255.4±20.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氯噻吩-2-羧酸乙酯 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-氯-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis

  摘要：

  A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 mu M, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 mu M), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.

  DOI：

  10.1021/jm100619x
• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 N-氯代丁二酰亚胺 、 三氟甲磺酸 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以53%的产率得到3-氯噻吩-2-羧酸乙酯
  参考文献：
  名称：

  区域和化学选择性C ？弱配位的H氯化/缺电子芳烃的溴化和相对方向基团能力的研究

  摘要：

  都是相对的：已经开发了一种实用而有效的Pd II催化的区域和化学选择性氯化/溴化反应，可轻松合成各种芳族氯化物。该反应显示出优异的反应活性，良好的官能团耐受性和高收率。进行了一项初步研究，以评估各种功能的相对指导能力。

  DOI：

  10.1002/anie.201300176

文献信息

• Novel fused pyrrolocarbazoles
  申请人：Hudkins L. Robert

  公开号：US20050143442A1

  公开（公告）日：2005-06-30

  The present invention relates generally to selected fused pyrrolocarbazoles, including pharmaceutical compositions thereof and methods of treating diseases therewith. The present invention is also directed to intermediates and processes for making these fused pyrrolocarbazoles.

  本发明一般涉及选定的融合吡咯咯噻唑，包括其药物组合物以及用于治疗疾病的方法。本发明还涉及制备这些融合吡咯咯噻唑的中间体和方法。
• Insecticial 3-(2,6-disubstituted phenyl)-5-[4- or 5-arylthien-2- or -3-yl]-1,2,4-triazoles
  申请人：——

  公开号：US20030134748A1

  公开（公告）日：2003-07-17

  Triazole compounds having a 2,6-disubstituted-phenyl group in the 3-position, arylthien-2- or -3-yl in the 5-position and an alkyl group in the 1-position are effective in controlling lepidoptera, coleoptera, mites and other sucking pests.

  三唑类化合物，在3位具有2,6-二取代苯基，5位为芳基噻吩-2-或-3-基团，1位为烷基基团，对于控制鳞翅目、鞘翅目、螨类和其他吸食性害虫具有有效性。
• [EN] METHOD FOR THE MANUFACTURE OF THIP<br/>[FR] PROCEDE DE PRODUCTION DE THIP
  申请人：LUNDBECK & CO AS H

  公开号：WO2005023820A1

  公开（公告）日：2005-03-17

  The present invention relates to a new method of preparing gaboxadol (THIP), which is useful for treating sleep disorders. In particular a method of preparing THIP comprising reacting a compound of formula (8b) or a salt thereof with an acid, typically a mineral acid, to obtain THIP as an acid addition salt. The present invention also relates to several intermediates.

  本发明涉及一种制备Gaboxadol（THIP）的新方法，该方法对治疗睡眠障碍有用。具体而言，本发明涉及一种制备THIP的方法，包括将化合物式（8b）或其盐与酸（通常为矿酸）反应，以获得THIP作为酸加成盐的方法。本发明还涉及几种中间体。
• [EN] NOVEL FUSED PYRROLOCARBAZOLES<br/>[FR] NOUVEAUX PYRROLOCARBAZOLES FONDUS
  申请人：CEPHALON INC

  公开号：WO2005063763A1

  公开（公告）日：2005-07-14

  The present invention relates generally to selected fused pyrrolocarbazoles, including pharmaceutical compositions thereof and methods of treating diseases therewith. The present invention is also directed to intermediates and processes for making these fused pyrrolocarbazoles.

  本发明涉及选定的融合吡咯烷基咔唑，包括其医药组合物及用于治疗疾病的方法。本发明还涉及中间体和制备这些融合吡咯烷基咔唑的方法。
• [EN] METHOD FOR THE PREPARATION OF CITALOPRAM<br/>[FR] PROCEDE DE PREPARATION DE CITALOPRAM
  申请人：LUNDBECK & CO AS H

  公开号：WO2002016341A1

  公开（公告）日：2002-02-28

  Disclosed is a method for the preparation of citalopram comprising conversion of a compound of Formula VIII 1-[(3-dimethylamino)prop-3-yl]-1-(4-fluorophenyl)-5-Z-1,3-dihydroisobenzofuranwherein Z is halogen, to a compound of Formula IV 5-carboxy-1-(3-(N,N-dimethylamino)prop-1-yl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuranfollowed by conversion of the compound of Formula IV into citalopram. Methods for the preparation of the compound of Formula IV are also disclosed.

  本发明涉及一种制备西酞普兰的方法，包括将式VIII化合物1-[(3-二甲基氨基)丙基]-1-(4-氟苯基)-5-Z-1,3-二氢异苯并呋喃（其中Z为卤素）转化为式IV化合物5-羧基-1-(3-(N,N-二甲基氨基)丙基)-1-(4-氟苯基)-1,3-二氢异苯并呋喃，然后将式IV化合物转化为西酞普兰。本发明还公开了制备式IV化合物的方法。