dimethyl(dimethylethyl)<<(5-methyl-3-isoxazolyl)methyl>oxy>silane | 153168-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl(dimethylethyl)<<(5-methyl-3-isoxazolyl)methyl>oxy>silane
• 英文别名: 3-((tert-butyldimethylsilyloxy)methyl)-5-methylisoxazole；3-(tert-butyl-(dimethyl)silanyloxymethyl)-5-methyl-isoxazole；3-(tert-Butyldimethylsilyloxymethyl)-5-methylisoxazole；tert-butyl-dimethyl-[(5-methyl-1,2-oxazol-3-yl)methoxy]silane
• CAS: 153168-60-6
• 化学式: C₁₁H₂₁NO₂Si
• 分子量: 227.379
• InChiKey: RABAVWHHTGIPHO-UHFFFAOYSA-N

物化性质

• 沸点：
  270.1±25.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl(dimethylethyl)<<(5-methyl-3-isoxazolyl)methyl>oxy>silane 在 正丁基锂 、 四甲基乙二胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 19.92h， 生成 <<3-<5-<3-<2,6-dimethyl-4-<3-(5-methyl-1,2,4-oxaadiazolyl)>phenoxy>propyl>isoxazolyl>>methoxy>dimethyl(dimethylethyl)silane
  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-羟甲基-5-甲基异恶唑 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到dimethyl(dimethylethyl)<<(5-methyl-3-isoxazolyl)methyl>oxy>silane
  参考文献：
  名称：

  通过铑卡宾诱导异恶唑的环扩展一锅法合成高度官能化的吡啶

  摘要：

  已开发出高度官能化吡啶的简洁一锅法合成。反应序列中的第一步是将乙烯基卡宾铑正式插入到异恶唑的 NO 键上。加热后，插入产物发生重排，得到 1,4-二氢吡啶。然后DDQ氧化以31-84%的产率提供相应的吡啶。该过程已被证明适用于一系列类卡宾和异恶唑组分，并代表了合成功能化吡啶的独特断开策略。

  DOI：

  10.1021/ja803139k

文献信息

• 1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral
  申请人：Sterling Winthrop Inc.

  公开号：US05464848A1

  公开（公告）日：1995-11-07

  Compounds of the formula ##STR1## wherein: R.sub.1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, or cyanomethyl; Y is alkylene of 3 to 9 carbon atoms, R.sub.2 and R.sub.3 independently are hydrogen, alkyl, alkoxy, halo, cyano, trifluoromethyl and nitro; R.sub.4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, dihaloethyl, cycloalkyl, heterocyclyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, halo, thioalkyl, alkylthioalkyl, alkylthio, thio, 2,2,2-trifluoro-ethyl, (4-methylphenyl)sulfonyloxymethyl, N.dbd.Q or CON.dbd.Q, where N.dbd.Q is amino, alkylamino or dialkylamino; R.sub.5 is hydrogen or halo or alkyl.

  公式为##STR1##的化合物，其中：R.sub.1为烷基，烷氧基，羟基，环烷基，羟基烷基，烷氧基烷基，羟基烷氧基，烷基硫代烷基，烷基亚砜基烷基，烷基磺酰基烷基，氨基烷基，烷基氨基烷基，二烷基氨基烷基，烷氧羰基，羧基或氰甲基；Y为碳原子数为3至9的烷基，R.sub.2和R.sub.3独立地为氢，烷基，烷氧基，卤素，氰基，三氟甲基和硝基；R.sub.4为烷氧基，羟基，卤甲基，二卤甲基，三卤甲基，二卤乙基，环烷基，杂环烷基，烷氧羰基，羟基烷基，烷氧基烷基，烷基羧酸酯氧基烷基，氰基，卤素，硫代烷基，烷基硫代烷基，烷基硫，硫，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为氨基，烷基氨基或二烷基氨基；R.sub.5为氢或卤素或烷基。
• [EN] QUINOLINONE DERIVATIVES AS INHIBITORS OF C-FMS KINASE<br/>[FR] DERIVES DE QUINOLINONE EN TANT QU'INHIBITEURS DE C-FMS KINASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005009967A3

  公开（公告）日：2005-03-24
• Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity
  作者：Guy D. Diana、Deborah L. Volkots、Theodore J. Nitz、Thomas R. Bailey、Melody A. Long、Niranjan Vescio、Suzanne Aldous、Daniel C. Pevear、Frank J. Dutko

  DOI：10.1021/jm00041a022

  日期：1994.7

  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.
• One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium Carbenoid Induced Ring Expansion of Isoxazoles
  作者：James R. Manning、Huw M. L. Davies

  DOI：10.1021/ja803139k

  日期：2008.7.1

  A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-dihydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general

  已开发出高度官能化吡啶的简洁一锅法合成。反应序列中的第一步是将乙烯基卡宾铑正式插入到异恶唑的 NO 键上。加热后，插入产物发生重排，得到 1,4-二氢吡啶。然后DDQ氧化以31-84%的产率提供相应的吡啶。该过程已被证明适用于一系列类卡宾和异恶唑组分，并代表了合成功能化吡啶的独特断开策略。