1-ethyl-3-methylenecyclobutanecarboxylic acid | 286442-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethyl-3-methylenecyclobutanecarboxylic acid
• 英文别名: 1-ethyl-3-methylidenecyclobutane-1-carboxylic acid
• CAS: 286442-84-0
• 化学式: C₈H₁₂O₂
• mdl: MFCD19231381
• 分子量: 140.182
• InChiKey: DSDFHBXNKCLABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethyl-3-methylenecyclobutanecarboxylic acid 在 盐酸 作用下， 反应 2.0h， 以100%的产率得到1-ethyl-3-chloro-3-methylcyclobutanecarboxylic acid
  参考文献：
  名称：

  Cyclobutane carboxamide inhibitors of fungal melanin: biosynthesis and their evaluation as fungicides

  摘要：

  A new fungicide lead has been identified by enzyme screening of a focused combinatorial library. The lead compound 4, a potent inhibitor of scytalone dehydratase (SD), exhibits fungicidal activity upon foliar application but does not show systemic activity. The X-ray crystal structure of the enzyme-inhibitor complex and an appreciation for the relationship between physical properties and systemic activity enabled us to rapidly improve upon this initial lead. The geminal halogen-methyl group combination was found to be optimal for interaction with the bounding serine and asparagine side-chain residues. Replacement of CF3 with methyl was a key discovery, giving inhibitors with slightly diminished enzyme inhibition potency while significantly increasing systemic activity. Amides prepared from amines with 2,4-dichloro substitution on the phenyl ring gave the most potent enzyme inhibitors. Two compounds from this series showed systemic activity comparable to the commercial standard and were selected for outdoor testing in flooded plots which simulate rice paddies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00034-1
• 作为产物：
  描述：

  3-亚甲基环丁烷羧酸 、 碘乙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以68%的产率得到1-ethyl-3-methylenecyclobutanecarboxylic acid
  参考文献：
  名称：

  Cyclobutane carboxamide inhibitors of fungal melanin: biosynthesis and their evaluation as fungicides

  摘要：

  A new fungicide lead has been identified by enzyme screening of a focused combinatorial library. The lead compound 4, a potent inhibitor of scytalone dehydratase (SD), exhibits fungicidal activity upon foliar application but does not show systemic activity. The X-ray crystal structure of the enzyme-inhibitor complex and an appreciation for the relationship between physical properties and systemic activity enabled us to rapidly improve upon this initial lead. The geminal halogen-methyl group combination was found to be optimal for interaction with the bounding serine and asparagine side-chain residues. Replacement of CF3 with methyl was a key discovery, giving inhibitors with slightly diminished enzyme inhibition potency while significantly increasing systemic activity. Amides prepared from amines with 2,4-dichloro substitution on the phenyl ring gave the most potent enzyme inhibitors. Two compounds from this series showed systemic activity comparable to the commercial standard and were selected for outdoor testing in flooded plots which simulate rice paddies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00034-1

文献信息

• Benzothiazole cyclobutyl amine derivatives
  申请人：Cowart D. Marlon

  公开号：US20070066588A1

  公开（公告）日：2007-03-22

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  公式（I）的化合物在治疗由组胺-3受体配体预防或改善的疾病或疾病中是有用的。还公开了包含组胺-3受体配体的药物组合物，使用这类化合物和组合物的方法，以及制备公式（I）范围内化合物的过程。
• BENZOTHIAZOLE CYCLOBUTYL AMINE DERIVATIVES
  申请人：Cowart Marlon D.

  公开号：US20090326222A1

  公开（公告）日：2009-12-31

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  公式（I）的化合物在治疗由组胺-3受体配体预防或改善的疾病或疾病方面非常有用。还公开了包含组胺-3受体配体的药物组合物，使用此类化合物和组合物的方法以及制备公式（I）范围内化合物的过程。
• Benzothiazole cyclobutyl amine derivatives and their use as histamine-3 receptors ligands
  申请人：Abbott Laboratories

  公开号：EP2386556A1

  公开（公告）日：2011-11-16

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  式（I）化合物可用于治疗组胺-3 受体配体所预防或改善的病症或紊乱。还公开了包含组胺-3 受体配体的药物组合物、使用此类化合物和组合物的方法以及制备式（I）范围内化合物的工艺。
• BENZOTHIAZOLE CYCLOBUTYL AMINE DERIVATIVES AND THEIR USE AS HISTAMINE-3 RECEPTORS LIGANDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1926729A1

  公开（公告）日：2008-06-04
• US7576110B2
  申请人：——

  公开号：US7576110B2

  公开（公告）日：2009-08-18