1-bromo-3,3-dimethoxy-butan-2-one | 69924-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-3,3-dimethoxy-butan-2-one
• 英文别名: 1-Bromo-3,3-dimethoxybutan-2-one
• CAS: 69924-69-2
• 化学式: C₆H₁₁BrO₃
• 分子量: 211.056
• InChiKey: HLMDBKPFKQTVIT-UHFFFAOYSA-N

物化性质

• 沸点：
  249.3±25.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-3,3-dimethoxy-butan-2-one 、 半胱胺盐酸盐 以 乙腈 为溶剂， 反应 3.0h， 以56%的产率得到1-(3,4-二氢-2H-1,4-噻嗪-5-基)乙酮
  参考文献：
  名称：

  Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant

  摘要：

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.

  DOI：

  10.1021/jf971004z
• 作为产物：
  描述：

  N-(3,3,-dimethoxy-2-butylidene)isopropylamine 在 N-溴代丁二酰亚胺(NBS) 、 草酸 作用下， 以 四氯化碳 、 乙醚 、 水 为溶剂， 反应 6.0h， 生成 1-bromo-3,3-dimethoxy-butan-2-one
  参考文献：
  名称：

  Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant

  摘要：

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.

  DOI：

  10.1021/jf971004z

文献信息

• Fluorescent and phosphorescent pyrimidine labels
  作者：Yong J. Lee、William A. Summers、John G. Burr

  DOI：10.1016/0040-4020(78)88003-x

  日期：1978.1

  syntheses of 1-(3,4-dioxopentyl)uracil (V), 1-(2,3-dioxobutyl)uracil (XIIa), 1-(2,3-dioxobutyl)-3-methyluracil (XIIb) and 1-(2,3-dioxobutyl)thymine (XIIc) are described. These are the first compounds to be prepared which have α-diketone functions attached to biologically important pyrimidines. Preparation of the dioxopentyluracil was by oximation of 1-(4-oxopentyl)uracil, and of the dioxobutyl compounds

  1-（3,4-二氧戊基）尿嘧啶（V），1-（2,3-二氧丁基）尿嘧啶（XIIa），1-（2,3-二氧丁基）-3-甲基尿嘧啶（XIIb）和1-的合成描述了（2，3-二氧丁基）胸腺嘧啶（XIIc）。这些是首先制备的具有与生物重要的嘧啶连接的α-二酮功能的化合物。二氧戊基尿嘧啶的制备是通过对1-（4-氧戊基）尿嘧啶的肟化来进行的，二氧丁基化合物是通过适当的嘧啶与溴联乙酰基的二甲氧基缩酮的烷基化，然后在特殊条件下进行水解而制备的。介绍并讨论了在各种溶剂中的吸收和发射光谱的特征。二氧戊环尿嘧啶在室温下既显示磷光又显示荧光。在相同条件下，二氧丁基嘧啶是荧光的，但不是磷光的。
• Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant
  作者：Norbert G. De Kimpe、Maria Teresa Rocchetti

  DOI：10.1021/jf971004z

  日期：1998.6.1

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.