5-(3-氯丙基)-3-甲基异噁唑 | 130800-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3-氯丙基)-3-甲基异噁唑
• 英文名称: 3-(3-methylisoxazol-5-yl)propyl chloride
• 英文别名: 5-(3-chloropropyl)-3-methylisoxazole；5-(3-chlorpropyl)-3-methylisoxazole；5-(3-chloropropyl)-3-methyl-1,2-oxazole
• CAS: 130800-76-9
• 化学式: C₇H₁₀ClNO
• 分子量: 159.615
• InChiKey: WKCCXMQDJNSMOT-UHFFFAOYSA-N

物化性质

• 沸点：
  249.3±25.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(3-氯丙基)-3-甲基异噁唑 在 盐酸羟胺 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 78.0h， 生成 N-hydroxy-3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>benzenecarboxamide imine
  参考文献：
  名称：

  Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity

  摘要：

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.

  DOI：

  10.1021/jm00041a022
• 作为产物：
  描述：

  3-甲基-5-异噁唑丙醇 生成 5-(3-氯丙基)-3-甲基异噁唑
  参考文献：
  名称：

  1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  式为##STR1##的化合物，其中：R.sub.1是烷基、烷氧基、羟基、环烷基、羟基烷基、烷氧基烷基或羟基烷氧基；Y是3至9个碳原子的脂肪基；R.sub.2和R.sub.3独立地是氢、烷基、烷氧基、卤素、三氟甲基和硝基；R.sub.4是烷氧基、羟基、卤代甲基、二卤代甲基、三卤代甲基、环烷基、烷氧羰基、羟基烷基、烷氧基烷基、烷基羧酸酯氧基烷基、氰基、2,2,2-三氟乙基、(4-甲基苯基)磺酰氧甲基、N.dbd.Q或CON.dbd.Q，其中N.dbd.Q是氨基、烷基氨基或二烷基氨基；或其药学上可接受的酸加成盐可用作抗病毒剂。

  公开号：

  US05349068A1

文献信息

• Conformationally restricted analogs of disoxaril: a comparison of the activity against human rhinovirus type 14 and 1A
  作者：John P. Mallamo、Guy D. Diana、Daniel C. Pevear、Frank J. Dutko、Michael S. Chapman、Kyung H. Kim、Iwona Minor、Marcos Oliveira、Michael G. Rossmann

  DOI：10.1021/jm00103a006

  日期：1992.12

  A series of conformationally restricted analogs of disoxaril has been synthesized and evaluated against human rhinovirus types (HRV) 14 and 1A. The sensitivity of these serotypes to this series varied and was dependent upon the length of the molecule as well as upon the flexibility of the aliphatic chain. Minimum energy conformations of these compounds were overlaid with the X-ray structure of a closely

  已经合成了一系列二恶草腈的构象受限的类似物，并针对人鼻病毒类型（HRV）14和1A进行了评估。这些血清型对该系列的敏感性变化并且取决于分子的长度以及脂族链的柔性。这些化合物的最小能量构象被与HRV-14和-1A的衣壳蛋白结合的密切相关类似物9的X射线结构重叠，然后在两种血清型的化合物结合位点建模。这些化合物在异恶唑环周围的相对吹扫体积显示出顺式烯烃8b的空间不可及，而反式烯烃8a或乙炔5都不是。
• 1,3,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral
  申请人：Sterling Drug Inc.

  公开号：US04945164A1

  公开（公告）日：1990-07-31

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; R' is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is selected from 1,3,4-oxadiazol-2-yl and 5-alkylated derivatives thereof, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；R'是1-5个碳原子的低烷基或羟基低烷基；R.sub.1和R.sub.2是氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；而Het是选自1,3,4-噁二唑-2-基和其5-烷基衍生物，可用作抗病毒剂，特别是对抗许多种鼻病毒的畸变病毒。
• Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0413289A2

  公开（公告）日：1991-02-20

  Compounds of the formulas wherein: Y is an alkylene bridge of 3-9 carbon atoms; R′ is lower-alkyl or hydroxy-lower-alkyl of 1-5 carbon atoms; R₁ and R₂ are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and R₈ is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when R₈ is hydrogen R′ is hydroxy-­lower-alkyl, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  分子式如下的化合物 其中 Y 是 3-9 个碳原子的烯桥； R′ 是 1-5 个碳原子的低级烷基或羟基低级烷基； R₁ 和 R₂ 是氢、卤素、低级烷基、低级烷氧基、硝基、低级烷氧羰基或三氟甲基；以及 R₈ 是氢或 1-5 个碳原子的低级烷基，但当 R₈ 是氢时，R′ 是羟基-低级烷基、 可用作抗病毒剂，尤其是抗皮卡病毒，包括多种鼻病毒。
• 1,2,4-Oxadiazolyl-phenoxy-alkylisoxazoles and their use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0523803A1

  公开（公告）日：1993-01-20

  Compounds of the formula wherein:    Y is alkylene of 3 to 9 carbon atoms;    R₁ is lower-alkyl, lower-alkoxy-(C₁₋₃-alkyl), lower-alkoxycarbonyl, cyclopropyl or trifluoromethyl;    R₂ and R₃ independently are hydrogen, lower-alkyl, halogen, lower-alkoxy, nitro, trifluoromethyl or hydroxy; and    R₄ is hydrogen or lower-alkyl; where lower-alkyl and lower-alkoxy, each occurrence, have from 1-5 carbon atoms;    with the proviso that when R₁ is lower-alkyl, at least one of R₂ and R₃ is hydroxy; or pharmaceutically acceptable acid-addition salts thereof, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  式中的化合物 其中 Y 是 3 至 9 个碳原子的亚烷基； R₁ 是低级烷基、低级烷氧基（C₁₋₃-烷基）、低级烷氧基羰基、环丙基或三氟甲基； R₂ 和 R₃ 独立地为氢、低级烷基、卤素、低级烷氧基、硝基、三氟甲基或羟基；以及 R₄ 是氢或低级烷基；其中低级烷基和低级烷氧基各自具有 1-5 个碳原子； 但当 R₁ 是低级烷基时，R₂ 和 R₃ 中至少有一个是羟基；或其药学上可接受的酸加成盐、 可用作抗病毒剂，尤其是抗皮卡病毒，包括多种鼻病毒株。
• 1,2,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use a s antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0566199A1

  公开（公告）日：1993-10-20

  Compounds of the formula wherein : R1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl or hydroxyalkoxy ; Y is alkylene of 3 to 9 carbon atoms, R2 and R3 independently are hydrogen, alkyl, alkoxy, halo, trifluoromethyl or nitro ; R4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, cycloalkyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, 2,2,2-trifluoroethyl, (4-methylphenyl)sulfonyloxymethyl, N=Q or CON=Q, where N=Q is amino, alkylamino or dialkylamino; or pharmaceutically acceptable acid-addition salts thereof are useful as antiviral agents. Preferred compounds are those wherein Y is alkylene of 3 to 5 carbon atoms and especially when R2 and R3 are in the 2- and 6- positions of the phenyl ring.

  式中的化合物 其中： R1 是烷基、烷氧基、羟基、环烷基、羟基烷基、烷氧基烷基或羟基烷氧基； Y 是 3 至 9 个碳原子的亚烷基、 R2 和 R3 分别是氢、烷基、烷氧基、卤代、三氟甲基或硝基； R4 是烷氧基、羟基、卤代甲基、二卤代甲基、三卤代甲基、环烷基、烷氧基羰基、羟基烷基、烷氧基烷基、烷羰氧基烷基、氰基、2,2,2-三氟乙基、（4-甲基苯基）磺酰氧基甲基、N=Q 或 CON=Q，其中 N=Q 是氨基、烷基氨基或二烷基氨基；或其药学上可接受的酸加成盐可用作抗病毒剂。 优选的化合物是其中 Y 为 3 至 5 个碳原子的亚烷基，特别是当 R2 和 R3 位于苯基环的 2- 和 6- 位时。