Cyclobutanecarboxylic acid, 3-ethyl-3-hydroxy-1-methyl-, cis- (9CI) | 286442-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cyclobutanecarboxylic acid, 3-ethyl-3-hydroxy-1-methyl-, cis- (9CI)
• 英文别名: cis-3-ethyl-3-hydroxy-1-methylcyclobutanecarboxylic acid
• CAS: 286442-90-8
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: UETHDRUFABRJDR-OCAPTIKFSA-N

物化性质

• 沸点：
  276.4±33.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Cyclobutanecarboxylic acid, 3-ethyl-3-hydroxy-1-methyl-, cis- (9CI) 、 (R)-(+)-1-(4-溴苯基)乙胺盐酸盐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以16%的产率得到cis-(R)-3-ethyl-3-hydroxy-1-methyl-N-[1-(4-bromophenyl)ethyl]cyclobutanecarboxamide
  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：

  1-甲基-3-亚甲基环丁烷羧酸 在 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 Cyclobutanecarboxylic acid, 3-ethyl-3-hydroxy-1-methyl-, cis- (9CI)
  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