5-bromo-2,2,6-trimethyl-1,3-diox-5-in-4-one | 104687-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-2,2,6-trimethyl-1,3-diox-5-in-4-one
• 英文别名: 2,2,6-trimethyl-5-bromo-1,3-dioxin-4-one；5-bromo-2,2,6-trimethyl-4H-1,3-dioxin-4-one；4H-1,3-Dioxin-4-one, 5-bromo-2,2,6-trimethyl-；5-bromo-2,2,6-trimethyl-1,3-dioxin-4-one
• CAS: 104687-80-1
• 化学式: C₇H₉BrO₃
• 分子量: 221.051
• InChiKey: BUYXYSZFWWMPCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  5-bromo-2,2,6-trimethyl-1,3-diox-5-in-4-one 、 苯基三氟硼酸钾 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氢氧化铵 作用下， 以 水 为溶剂， 以35%的产率得到5-phenyl-2,2,6-trimethyl-2h,4h-1,3-dioxin-4-one
  参考文献：
  名称：

  Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters

  摘要：

  The high efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a-b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a-n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.027
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 在 溴 作用下， 以 二氯甲烷 为溶剂， 以16.5 g (75%)的产率得到5-bromo-2,2,6-trimethyl-1,3-diox-5-in-4-one
  参考文献：
  名称：

  5-halo-4H-1,3-dioxin-4-one compounds

  摘要：

  披露了新型的5-卤代-4H-1,3-二噁烷-4-酮及其制备方法，通过将具有以下分子式的化合物进行处理得到：##STR1## 其中X为Cl或Br，处理剂为X.sub.2或SO.sub.2 X.sub.2。

  公开号：

  US04582913A1

文献信息

• Preparation of .alpha.-haloacetoacetic esters
  申请人：Eastman Kodak Company

  公开号：US04633013A1

  公开（公告）日：1986-12-30

  Disclosed is a process for the preparation of .alpha.-haloacetoacetic esters by the reaction of an alkali metal alkoxide with a 5-halo-4H-1,3-dioxin-4-one compound, the desired product being obtained as an alkali metal salt which may be converted to the corresponding free ester by treating with acid.

  本发明公开了一种制备.alpha.-卤代乙酰乙酸酯的方法，该方法通过将碱金属烷氧化物与5-卤代-4H-1,3-二噁烷-4-酮化合物反应得到所需的产物，所得的产物为碱金属盐，可以通过用酸处理转化为相应的自由酯。
• [EN] 5-HALO-4H-1,3-DIOXIN-4-ONE COMPOUNDS, alpha -HALO-ACETOACETIC ESTERS PREPARED FROM SUCH COMPOUNDS AND PROCESS FOR THEIR PREPARATION
  申请人：EASTMAN KODAK COMPANY

  公开号：WO1986000068A1

  公开（公告）日：1986-01-03

  (EN) 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having formula (I), with X2 or SO2X2 wherein X is Cl or Br. The 5-halo-4H-1,3-dioxin-4-ones can then be reacted with an alkali metal alkoxide at a temperature of about -40oC. to about 50oC. to provide an $g(a)-haloaceto-acetic ester.(FR) L'invention concerne des 5-halo-4H-1,3-dioxine-4-ones et leur préparation en traitant un composé ayant la formule (I) avec X2 ou SO2X2, dans laquelle X représente Cl ou Br. Il est alors possible de faire réagir les 5-halo-4H-1,3-dioxine-4-ones avec un alkoxide de métal alcalin à une température d'environ -40oC jusqu'à environ 50oC, afin d'obtenir un ester $g(a)-haloacétoacétique.

  涉及的物质是5-卤代-1,3-二ioxin-4-酮类化合物及其制备方法。制备该类物质的方法是采用标有公式(I)的化合物，与X2或SO2X2（其中X代表Cl或Br）进行处理。随后，所述5-卤代-4H-1,3-二ioxin-4-酮可以与碱金属氧化物在-40°C至50°C之间进行反应，以获得g(a)-卤代乙酸乙酯。
• Bromination of 2,2,6-trialkyl-1,3-dioxan-4-ones. Application of the deuterium isotope effect to the synthesis of a chiral trialkyldioxinone
  作者：Gordon L. Lange、Michael G. Organ、Michael R. Roche

  DOI：10.1021/jo00048a039

  日期：1992.10

  Free-radical bromination (2 equiv of NBS) of 2-tert-butyl-2,6-dimethyl-1,3-dioxan-4-one (6a) gives the 2-bromomethyl product 7a. By contrast, bromination of 2-tert-butyl-2-methyl-1,3-dioxan-4-one (1) is reported to occur at the 6-position. Deuterium-labeling experiments established that 7a is formed by direct substitution at the 2-methyl group of 6a and not by abstraction of H-6 followed by hydrogen atom transfer from the 2-methyl group and bromination of the resultant primary radical 12. When 2-tert-butyl-6-methyl-2-(methyl-d3)-1,3-dioxan-4-one (13) is reacted with 4 equiv of NBS, the course of the reaction is altered dramatically and the major product formed in high yield is dioxinone 16. Thus, a trideuteriomethyl group directs bromination away from the 2-methyl site to H-6. Bromination at the 6-position followed by loss of HBr, addition of Br2, and loss of a second HBr gives 16. Dioxinone 14, a valuable substrate for asymmetric induction studies, is formed in high yield by reductive debromination of 16. When (R)-3-hydroxybutyric acid is used in the preparation of 13, optically pure (-)-14 is obtained using the sequence described.
• CLEMEENS, R. J.
  作者：CLEMEENS, R. J.

  DOI：——

  日期：——
• 5-HALO-4H-1,3-DIOXIN-4-ONE COMPOUNDS, $g(a)-HALO-ACETOACETIC ESTERS PREPARED FROM SUCH COMPOUNDS AND PROCESS FOR THEIR PREPARATION
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0183797A1

  公开（公告）日：1986-06-11