methyl 2-chloroazulene-1-carboxylate | 54798-16-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: methyl 2-chloroazulene-1-carboxylate
• 英文别名: 2-Chlor-1-methoxycarbonyl-azulen
• CAS: 54798-16-2
• 化学式: C₁₂H₉ClO₂
• 分子量: 220.655
• InChiKey: NEGWKGRSCUPKQG-UHFFFAOYSA-N

物化性质

• 沸点：
  337.4±15.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  methyl 2-chloroazulene-1-carboxylate 在 氢氧化钾 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-Azulyl)ethanol
  参考文献：
  名称：

  Nonbenzenoid aromatic systems. XI. Synthesis and buffered acetolysis of 2-(2-azulyl)ethyl tosylate and nosylate

  摘要：

  DOI：

  10.1021/jo00900a002
• 作为产物：
  描述：

  二乙基2-氯-1,3-薁二羧酸酯 以 四氯化碳 为溶剂， 生成 methyl 2-chloroazulene-1-carboxylate
  参考文献：
  名称：

  Nonbenzenoid aromatic systems. XI. Synthesis and buffered acetolysis of 2-(2-azulyl)ethyl tosylate and nosylate

  摘要：

  DOI：

  10.1021/jo00900a002
• 作为试剂：
  描述：

  methyl 2-chloroazulene-1-carboxylate 、 (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-[2-acetyloxy-5-(bromomethyl)phenyl]-D-glucitol 在 methyl 2-chloroazulene-1-carboxylate 作用下， 生成
  参考文献：
  名称：

  Bioorg. Med. Chem. 2013, 21, 3934-3948

  摘要：

  DOI：

文献信息

• Azulene derivatives and salts thereof
  申请人：Tomiyama Hiroshi

  公开号：US20050124555A1

  公开（公告）日：2005-06-09

  The present invention provides an azulene derivative and a salt thereof, wherein an azulene ring is bonded to a benzene ring directly or via a lower alkylene which may be substituted with a halogen atom and the benzene ring is directly bonded to the glucose residue, and it is usable as a Na + -glucose cotransporter inhibitor, especially for a therapeutic and/or preventive agent for diabetes such as insulin-dependent diabetes (type 1 diabetes) and insulin-independent diabetes (type 2 diabetes), as well as diabetes-related diseases such as insulin-resistant diseases and obesity.

  本发明提供了一种吲哚蓝衍生物及其盐，其中吲哚蓝环直接或通过可被取代为卤原子的较低烷基与苯环结合，苯环直接与葡萄糖残基结合，可用作Na+-葡萄糖共转运蛋白抑制剂，特别用于治疗和/或预防糖尿病，如胰岛素依赖型糖尿病（1型糖尿病）和胰岛素非依赖型糖尿病（2型糖尿病），以及糖尿病相关疾病，如胰岛素抵抗性疾病和肥胖症。
• 2-phenylazulene derivatives and a manufacturing method of these compounds
  申请人：Kotobuki Seiyaku Co., Ltd.

  公开号：US05843999A1

  公开（公告）日：1998-12-01

  A series of new azulene derivatives are disclosed, which are represented by the following formula; ##STR1## wherein: R.sub.1 is hydrogen atom, lower alkoxycarbonyl group, carboxy group, halogen atom, lower alkyl group, phenyl group or lower alkanoyl group; R.sub.2, R.sub.3 and R.sub.4 are hydrogen atom, lower alkyl group, lower alkoxy group or halogen atom; X is lower alkyl group or amino group. The compounds of the present invention are useful for treatment of inflammation.

  本发明公开了一系列新的蓝紫烯衍生物，其表示为以下式子：##STR1## 其中：R.sub.1是氢原子，低烷氧羰基基团，羧基，卤原子，低烷基，苯基或低烷酰基基团; R.sub.2，R.sub.3和R.sub.4是氢原子，低烷基，低烷氧基或卤原子; X是低烷基或氨基。本发明的化合物对于治疗炎症具有有用性。
• AZULENE DERIVATIVES AND SALTS THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1553094A1

  公开（公告）日：2005-07-13

  The present invention provides an azulene derivative and a salt thereof, wherein an azulene ring is bonded to a benzene ring directly or via a lower alkylene which may be substituted with a halogen atom and the benzene ring is directly bonded to the glucose residue, and it is usable as a Na+-glucose cotransporter inhibitor, especially for a therapeutic and/or preventive agent for diabetes such as insulin-dependent diabetes (type 1 diabetes) and insulin-independent diabetes (type 2 diabetes), as well as diabetes-related diseases such as insulin-resistant diseases and obesity.

  本发明提供了一种偶氮烯衍生物及其盐，其中偶氮烯环直接或通过可被卤原子取代的低级亚烷基与苯环键合，苯环直接与葡萄糖残基键合、可用作 Na+-葡萄糖共转运体抑制剂，特别是用于治疗和/或预防糖尿病，如胰岛素依赖型糖尿病（1 型糖尿病）和胰岛素非依赖型糖尿病（2 型糖尿病），以及与糖尿病相关的疾病，如胰岛素抵抗性疾病和肥胖症。
• Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: Discovery of YM543
  作者：Kazuhiro Ikegai、Masakazu Imamura、Takayuki Suzuki、Keita Nakanishi、Takeshi Murakami、Eiji Kurosaki、Atsushi Noda、Yoshinori Kobayashi、Masayuki Yokota、Tomokazu Koide、Kazuhiro Kosakai、Yasufumi Ohkura、Makoto Takeuchi、Hiroshi Tomiyama、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2013.03.067

  日期：2013.7

  Here, a series of C-glucosides with azulene rings in the aglycon moiety was synthesized and the inhibitory activities toward hSGLT1 and hSGLT2 were evaluated. Starting from the azulene derivative 7 which had relatively good SGLT2 inhibitory activity, compound 8a which has a 3-[(azulen-2-yl)methyl]phenyl group was identified as a lead compound for further optimization. Introduction of a phenolic hydroxyl group onto the central benzene ring afforded a potent and selective SGLT2 inhibitor 8e, which reduced blood glucose levels in a dose-dependent manner in rodent diabetic models. A mono choline salt of 8e (YM543) was selected as a clinical candidate for use in treating type 2 diabetes mellitus. (C) 2013 Elsevier Ltd. All rights reserved.
• US5843999A
  申请人：——

  公开号：US5843999A

  公开（公告）日：1998-12-01