2-醛基-5-甲氧基苯并噻吩 | 622864-56-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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-醛基-5-甲氧基苯并噻吩
• 中文别名: 5-甲氧基苯并噻吩-2-甲醛
• 英文名称: 5-methoxy-1-benzo[b]thiophene-2-carbaldehyde
• 英文别名: 5-methoxybenzo[b]thiophene-2-carbaldehyde；5-methoxy-1-benzothiophene-2-carbaldehyde
• CAS: 622864-56-6
• 化学式: C₁₀H₈O₂S
• mdl: MFCD11101036
• 分子量: 192.238
• InChiKey: BUOLMHIRVKNQJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.4±22.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件为2-8°C，避光，并保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  2-醛基-5-甲氧基苯并噻吩 在 manganese(IV) oxide 、 tin(ll) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 环己烷 、 甲苯 为溶剂， 反应 269.0h， 生成 9-methoxy-4-phenyl-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  4-甲氧基茴香硫醚 、 N,N-二甲基甲酰胺 在 正丁基锂 、 四甲基乙二胺 作用下， 以 甲基叔丁基醚 为溶剂， 反应 27.5h， 以20%的产率得到2-醛基-5-甲氧基苯并噻吩
  参考文献：
  名称：

  硫代苯甲醚双骨架化合物的制备和CH锂化/环化反应，可用于五元杂环

  摘要：

  报道了基于硫代苯甲醚的三锂配合物的合成，分离和X射线结构。在双重锂化策略的基础上，在温和的反应条件（室温）下开发了两种新颖的合成方法：（1）锂硫代苯甲醚与腈的反应通过[3 + 2]型方法得到苯并异噻唑，其中两种新的键形成和（2）通过[4 +1]模式由硫代苯甲醚和酰胺形成苯并噻吩，形成4个新的化学键。

  DOI：

  10.1021/acs.orglett.8b00850

文献信息

• [EN] INHIBITORS OF CHECKPOINT KINASES (WEE1 AND CHK1)<br/>[FR] INHIBITEURS DE CHECKPOINT KINASES (WEE1 ET CHK1)
  申请人：WARNER LAMBERT CO

  公开号：WO2003091255A1

  公开（公告）日：2003-11-06

  This invention relates to pyrrolocarbazole derivatives according formula (I) wherein R1, R2, r7, R8 R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1.

  本发明涉及公式（I）中的吡咯并咔唑衍生物，其中R1，R2，r7，R8，R9，X和Y如规范中所定义，其中所述衍生物特异性地抑制检查点激酶Wee1和Chk1中的一个或两个。
• Process for oxidation of alcohols
  申请人：——

  公开号：US20040147787A1

  公开（公告）日：2004-07-29

  The use of iodine as a primary oxidant for TEMPO provides a novel and selective method for oxidizing alcohols to their corresponding carbonyl compounds.

  使用碘作为 TEMPO 的主氧化剂，为将醇氧化成相应的羰基化合物提供了一种新颖的选择性方法。
• INHIBITORS OF CHECKPOINT KINASES (WEE1 AND CHK1)
  申请人：WARNER-LAMBERT COMPANY LLC

  公开号：EP1501831A1

  公开（公告）日：2005-02-02
• CHEMILUMINESCENT COMPOSITIONS, METHODS, ASSAYS AND KITS FOR OXIDATIVE ENZYMES
  申请人：Juo Rouh-Rong

  公开号：US20120100566A1

  公开（公告）日：2012-04-26

  Chemiluminescent compositions, methods, assays and kits for oxidative enzymes are described. Further disclosed are dioxetane compounds of the form: 0-0 ΛR R R T (i) where R can independently be any branched alkyl or cycloalkyl group which provides stabilization for the dioxetane or where both R groups together form a cycloalkyl or polycycloalkyl moiety spiro bound to the dioxetane ring, wherein each R group or the spiro bound moiety can be unsubstituted or substituted with one or more electron-withdrawing groups or electron donating groups, or groups providing preferential oxidative isozyme substrate recognition, and wherein Ri is an aryl group, or an alkyl group of 1-20 carbon atoms, which can be optionally substituted with 1 or more halogen atoms, and wherein T is an aryl or heteroaryl ring capable of emitting light upon enzyme activated decomposition of the dioxetane I. Kits, methods and assays are also disclosed that comprise the dioxetane compounds.
• US7094798B1
  申请人：——

  公开号：US7094798B1

  公开（公告）日：2006-08-22