methyl 3-cyclohexyl-2-iodo-2-propenate | 126628-67-9

• 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 3-cyclohexyl-2-iodo-2-propenate
• 英文别名: methyl (Z)-3-cyclohexyl-2-iodoprop-2-enoate
• CAS: 126628-67-9
• 化学式: C₁₀H₁₅IO₂
• 分子量: 294.132
• InChiKey: QNJBTKSILCMUNP-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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 3-cyclohexyl-2-iodo-2-propenate 、 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-cyclohexyl-2-(4-(methanesulfonyl)-3-nitro-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 3-cyclohexyl-2-iodo-2-propenate
  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

• Heteroaromatic glucokinase activators
  申请人：——

  公开号：US20010039344A1

  公开（公告）日：2001-11-08

  2,3-Di-substituted N-heteroaromatic propionamides with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.

  2,3-二取代N-杂环丙酰胺，其中2-位取代为取代苯基，3-位取代为环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可增加胰岛素分泌，用于治疗2型糖尿病。
• Tetrazolyl-phenyl acetamide glucokinase activators
  申请人：——

  公开号：US20020035266A1

  公开（公告）日：2002-03-21

  Tetrazolyl-phenyl acetamides are active as glucokinase activators, and are able to increase insulin secretion, which makes them useful for treating type II diabetes.

  四唑基苯乙酰胺作为葡萄糖激酶激活剂具有活性，能够增加胰岛素分泌，因此对治疗2型糖尿病有用。
• Tetrazolyl-phenyl actamide glucokinase activators
  申请人：——

  公开号：US20020065275A1

  公开（公告）日：2002-05-30

  Tetrazolyl-phenyl acetamides are active as glucokinase activators, and are able to increase insulin secretion, which makes them useful for treating type II diabetes.

  Tetrazolyl-phenyl 醋酸酰胺具有活性，能够激活葡萄糖激酶，增加胰岛素分泌，因此对治疗II型糖尿病有用。
• Huang, Yao-Zeng; Shi, Li-Lan; Li, Sao-Wei, Synthetic Communications, 1989, vol. 19, # 15, p. 2639 - 2646
  作者：Huang, Yao-Zeng、Shi, Li-Lan、Li, Sao-Wei、Huang, Rong

  DOI：——

  日期：——
• HUANG, YAO-ZENG;SHI, LI-LAN;LI, SAO-WEI;HUANG, RONG, SYNTH. COMMUN., 19,(1989) N5, C. 2639-2646
  作者：HUANG, YAO-ZENG、SHI, LI-LAN、LI, SAO-WEI、HUANG, RONG

  DOI：——

  日期：——