4-t-butylbenzyl bromoacetate | 405521-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-t-butylbenzyl bromoacetate
• 英文别名: (4-tert-butylphenyl)methyl 2-bromoacetate
• CAS: 405521-74-6
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: VQTHCXQMDFKFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-t-butylbenzyl bromoacetate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以1.1 g的产率得到4-(tert-butyl)benzyl 2-azidoacetate
  参考文献：
  名称：

  A Photoinduced, Benzyne Click Reaction

  摘要：

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.

  DOI：

  10.1021/ol500389t
• 作为产物：
  描述：

  4-叔丁基苄醇 、 溴乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 4-t-butylbenzyl bromoacetate
  参考文献：
  名称：

  A Photoinduced, Benzyne Click Reaction

  摘要：

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.

  DOI：

  10.1021/ol500389t

文献信息

• 2,3-Dihydro-4H-1,3-oxazin-4-ones, Novel Auxiliaries for the Stereoselective Synthesis of 1β-methylcarbapenems
  作者：Do K. Pyun、Won J. Jeong、Hee J. Jung、Jae H. Kim、Jin S. Lee、Cheol H. Lee、Bong J. Kim

  DOI：10.1055/s-2001-18778

  日期：——

  as efficient auxiliaries for the stereoselective synthesis of β-methylcarbapenem intermediate 2. Reformatsky-type reactions of 4-acetoxyazetidinone with α-bromopropionyl dihydrooxazinone 10 provided β-methylazetidinones 4 in high diastereoselectivities. The auxiliaries 9 were also easily removed in the Dieckmann cyclization leading to β-methylcarbapenem skeletons. Practical synthesis of β-methylenolphosphates

  二氢恶嗪酮 9 由苄基氰分两步制备，可作为立体选择性合成 β-甲基碳青霉烯中间体 2 的有效助剂。 4-乙酰氧基氮杂环丁酮与 α-溴丙酰二氢恶嗪酮 10 的 Reformatsky 型反应提供了具有高非对映选择性的 β-甲基氮杂环丁酮 4。在导致β-甲基碳青霉烯骨架的Dieckmann环化中，助剂9也很容易去除。从 4-乙酰氧基氮杂环丁酮 3 实际合成 β-亚甲基磷酸酯 2 分三步完成（总产率为 61-77%）。