methyl 1,5-dioxa-9-thiaspiro[5.5]undecane-7-carboxylate | 189947-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1,5-dioxa-9-thiaspiro[5.5]undecane-7-carboxylate
• 英文别名: Methyl 1,5-dioxa-9-thiaspiro[5.5]undecane-11-carboxylate
• CAS: 189947-42-0
• 化学式: C₁₀H₁₆O₄S
• 分子量: 232.301
• InChiKey: ZGJPNQSNNUHPAU-UHFFFAOYSA-N

物化性质

• 沸点：
  333.7±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1,5-dioxa-9-thiaspiro[5.5]undecane-7-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1,5-dioxa-9-thiaspiro[5.5]undecane-7-carboxylic acid
  参考文献：
  名称：

  Using the Electrostatic Field Effect to Design a New Class of Inhibitors for Cysteine Proteases

  摘要：

  A new class of competitive inhibitors for the cysteine protease papain is described. These inhibitors are based upon a 4-heterocyclohexanone ring and are designed to react with the enzyme active site nucleophile to give a reversibly formed hemithioketal. The electrophilicity of the ketone in these inhibitors is enhanced by ring strain and by through-space electrostatic repulsion with the heteroatom at the 1-position of the ring. Equilibrium constants for addition of water and 3-mercaptopropionic acid to several 4-heterocyclohexanones were measured by H-1 NMR spectroscopy. These reactions model addition of the active site nucleophile to the corresponding inhibitors. The equilibrium constants give a linear correlation with the field substituent constant F for the functional group at the 1-position of the heterocyclohexanone. These equilibrium constants also correlate well with the inhibition constants for the 4-heterocyclohexanone-based inhibitors, which range from 11 to 120 mu M. Thus, the model system can be used to predict the potency of structurally related enzyme inhibitors.

  DOI：

  10.1021/ja9641867
• 作为产物：
  描述：

  四氢-4-氧代-2H-噻喃-3-甲酸甲酯 、 1,3-丙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 10.0h， 以52%的产率得到methyl 1,5-dioxa-9-thiaspiro[5.5]undecane-7-carboxylate
  参考文献：
  名称：

  [EN] NOVEL TRICYCLIC DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  [FR] NOUVEAUX DÉRIVÉS TRICYCLIQUES OU LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES, PROCÉDÉ DE PRÉPARATION DE CES DERNIERS ET COMPOSITION PHARMACEUTIQUE LES CONTENANT

  摘要：

  公开号：

  WO2009061131A3