methyl (Z)-3-cyclooctyl-2-iodoprop-2-enoate | 345635-24-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-3-cyclooctyl-2-iodoprop-2-enoate
• CAS: 345635-24-7
• 化学式: C₁₂H₁₉IO₂
• 分子量: 322.186
• InChiKey: JAAUSCFVZJENCX-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-cyclooctyl-2-iodoprop-2-enoate 、 alkaline earth salt of/the/ methylsulfuric acid 在 三甲基氯硅烷 、 锌 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 15.0h， 生成 (E)-3-cyclooctyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid methyl ester
  参考文献：
  名称：

  2,3-Disubstituted acrylamides as potent glucokinase activators

  摘要：

  The phenylacetamide 1 represents the archtypical glucokinase activator (GKA) in which only the R-isomer is active. In order to probe whether the chiral center could be replaced, we prepared a series of olefins 2 and show in the present work that these compounds represent a new class of GKAs. Surprisingly, the SAR of the new series paralleled that of the saturated derivatives with the exception that there was greater tolerance for larger alkyl and cycloalkyl groups at R-2 region in comparison to the phenylacetamides. In normal Wistar rats, the 2,3-disubstituted acrylamide analog 10 was well absorbed and demonstrated robust glucose lowering effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.029
• 作为产物：
  描述：

  丙炔酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 copper(l) cyanide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 methyl (Z)-3-cyclooctyl-2-iodoprop-2-enoate
  参考文献：
  名称：

  2,3-Disubstituted acrylamides as potent glucokinase activators

  摘要：

  The phenylacetamide 1 represents the archtypical glucokinase activator (GKA) in which only the R-isomer is active. In order to probe whether the chiral center could be replaced, we prepared a series of olefins 2 and show in the present work that these compounds represent a new class of GKAs. Surprisingly, the SAR of the new series paralleled that of the saturated derivatives with the exception that there was greater tolerance for larger alkyl and cycloalkyl groups at R-2 region in comparison to the phenylacetamides. In normal Wistar rats, the 2,3-disubstituted acrylamide analog 10 was well absorbed and demonstrated robust glucose lowering effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.029

文献信息

• TRANS OLEFINIC GLUCOKINASE ACTIVATORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1242397A1

  公开（公告）日：2002-09-25
• US6353111B1
  申请人：——

  公开号：US6353111B1

  公开（公告）日：2002-03-05
• [EN] TRANS OLEFINIC GLUCOKINASE ACTIVATORS<br/>[FR] ACTIVATEURS TRANSOLEFINIQUES DE GLUCOKINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2001044216A1

  公开（公告）日：2001-06-21

  2,3-Di-substituted trans olefinic N-heteroaromatic or urido proprionamides of formula (I) with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said proprionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.