5-tert-Butyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester | 154153-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-tert-Butyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-tert-butyl-4,5-dihydro-1,2-oxazole-3-carboxylate
• CAS: 154153-43-2
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: MFHUUSLUMNUDET-UHFFFAOYSA-N

物化性质

• 沸点：
  241.4±23.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-tert-Butyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.0h， 生成 5-tert-Butyl-3-chloromethyl-4,5-dihydro-isoxazole
  参考文献：
  名称：

  Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

  摘要：

  A series of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides and related compounds were synthesized and their antiviral activities against human influenza A virus were assessed. Studies of the structure-activity relationships revealed the strongest antiviral activity when position-5 of the isoxazoline ring was substituted with a tert-butyl group. When the alkoxyimino moiety was substituted with a methyl, ethyl, isopropyl or allyl group, good antiviral activity was obtained. Among the geometrical isomers at the oxime moiety, the E-isomers were more active than the Z-isomers. Among the compounds examined, (E)-2-allyloxyimino-2-cyano-N-(5-tert-butyl-2-iosaxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC50 of 3 mug/mL in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00362-6
• 作为产物：
  描述：

  ethyl chlorooximidoacetate 、 3,3-二甲基-1-丁烯 在 碳酸氢钠 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 生成 5-tert-Butyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Anti-influenza Virus Activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides

  摘要：

  A series of 2-alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides and related compounds were synthesized and their antiviral activities against human influenza A virus were assessed. Studies of the structure-activity relationships revealed the strongest antiviral activity when position-5 of the isoxazoline ring was substituted with a tert-butyl group. When the alkoxyimino moiety was substituted with a methyl, ethyl, isopropyl or allyl group, good antiviral activity was obtained. Among the geometrical isomers at the oxime moiety, the E-isomers were more active than the Z-isomers. Among the compounds examined, (E)-2-allyloxyimino-2-cyano-N-(5-tert-butyl-2-iosaxazolin-3-ylmethyl)acetamide (1j) was the most active inhibitor with an EC50 of 3 mug/mL in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00362-6

文献信息

• Silyl isoxazolines-2: synthesis, structure and properties
  作者：E. Lukevics、V. Dirnens、A. Kemme、J. Popelis

  DOI：10.1016/0022-328x(96)06358-9

  日期：1996.8

  Silyl isoxazolines have been synthesized by [2 + 3] cycloaddition reaction of nitrile oxides and silylnitronates to vinyl- and allylsilanes. The direction of the cycloaddition reaction of nitrile oxides to trialkoxyvinylsilanes has been shown to depend on the nature of the substituents on silicon and on the method used to generate the nitrile oxides. The addition of silyl esters of aci-nitromethane

  甲硅烷基异恶唑啉是通过腈氧化物和甲硅烷基亚硝酸盐的[2 + 3]环加成反应合成乙烯基硅烷和烯丙基硅烷而合成的。已显示腈氧化物与三烷氧基乙烯基硅烷的环加成反应的方向取决于硅上取代基的性质以及用于产生腈氧化物的方法。将三硝基硝基甲烷的甲硅烷基酯加到三乙氧基乙烯基硅烷中，得到5-甲硅烷基和4-甲硅烷基异构体。讨论了甲硅烷基异恶唑啉的结构。