(1S,5S,6S)-4-Chloro-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester | 195244-42-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (1S,5S,6S)-4-Chloro-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,5S,6S)-4-chloro-5-pentan-3-yloxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate
• CAS: 195244-42-9
• 化学式: C₁₃H₁₉ClO₄
• 分子量: 274.744
• InChiKey: IIQGISDYFTVNAM-ZMLRMANQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S)-4-Chloro-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester 在 sodium azide 、 氯化铵 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and activity of C2-substituted analogs of influenza neuraminidase inhibitor GS 4071

  摘要：

  The influence of C-2-substitution of GS 4071 on the influenza neuraminidase inhibitory activity was investigated. The introduction of lipophilic substituents (chloro, methyl, and methylthio) at the C-2 position resulted in a significant decrease of the activity. This result indicates that at the enzyme active site there is limited hydrophobic pocket for a group at the C-2 position of GS 4071. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00331-4
• 作为产物：
  描述：

  (3S,4S,5R)-2-Chloro-3,4,5-trihydroxy-cyclohex-1-enecarboxylic acid methyl ester 在 高氯酸 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (1S,5S,6S)-4-Chloro-5-(1-ethyl-propoxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and activity of C2-substituted analogs of influenza neuraminidase inhibitor GS 4071

  摘要：

  The influence of C-2-substitution of GS 4071 on the influenza neuraminidase inhibitory activity was investigated. The introduction of lipophilic substituents (chloro, methyl, and methylthio) at the C-2 position resulted in a significant decrease of the activity. This result indicates that at the enzyme active site there is limited hydrophobic pocket for a group at the C-2 position of GS 4071. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00331-4

文献信息

• Synthesis and activity of C2-substituted analogs of influenza neuraminidase inhibitor GS 4071
  作者：Lijun Zhang、Matthew A. Williams、Dirk B. Mendel、Paul A. Escarpe、Choung U. Kim

  DOI：10.1016/s0960-894x(97)00331-4

  日期：1997.7

  The influence of C-2-substitution of GS 4071 on the influenza neuraminidase inhibitory activity was investigated. The introduction of lipophilic substituents (chloro, methyl, and methylthio) at the C-2 position resulted in a significant decrease of the activity. This result indicates that at the enzyme active site there is limited hydrophobic pocket for a group at the C-2 position of GS 4071. (C) 1997 Elsevier Science Ltd.