4-Bromo-2-diazo-4,4-difluoro-3-oxo-butyric acid ethyl ester | 347341-06-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Bromo-2-diazo-4,4-difluoro-3-oxo-butyric acid ethyl ester
• 英文别名: Ethyl 4-bromo-2-diazo-4,4-difluoro-3-oxobutanoate
• CAS: 347341-06-4
• 化学式: C₆H₅BrF₂N₂O₃
• 分子量: 271.018
• InChiKey: WNCINRKUFUETKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Bromo-2-diazo-4,4-difluoro-3-oxo-butyric acid ethyl ester 在 Ph₂(OAc)4 硫酸 作用下， 以 四氯化碳 为溶剂， 生成 ethyl 3-bromodifluoromethyl-2-furancarboxylate
  参考文献：
  名称：

  A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions

  摘要：

  The rhodium(II)-catalyzed reactions of ethyl 2-diazo-fluoroalkylacetoacetate 1 with vinyl ethers have been studied. The reactions of 1a-e with isobutyl vinyl ethers afforded dihydrofuroates 3a-e in good to excellent yields. Further transformation of the dihydrofuroates by acid-catalyzed alcohol elimination could give alpha -fluoroalkyl-beta -furoates readily. Similarly, stable diazo compounds 1a and b reacted with cyclic vinyl ethers to give 1,3-dipolar cycloaddition products. Interestingly, only vinyl C-H insertion compound was obtained concerning the reaction of la with 2,5-dimethylfuran. The reaction mechanism was also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00183-1
• 作为产物：
  描述：

  ethyl 4-bromo-4,4-difluoro-3-oxo-butanoate 在 对甲苯磺酰叠氮 作用下， 生成 4-Bromo-2-diazo-4,4-difluoro-3-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions

  摘要：

  The rhodium(II)-catalyzed reactions of ethyl 2-diazo-fluoroalkylacetoacetate 1 with vinyl ethers have been studied. The reactions of 1a-e with isobutyl vinyl ethers afforded dihydrofuroates 3a-e in good to excellent yields. Further transformation of the dihydrofuroates by acid-catalyzed alcohol elimination could give alpha -fluoroalkyl-beta -furoates readily. Similarly, stable diazo compounds 1a and b reacted with cyclic vinyl ethers to give 1,3-dipolar cycloaddition products. Interestingly, only vinyl C-H insertion compound was obtained concerning the reaction of la with 2,5-dimethylfuran. The reaction mechanism was also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00183-1

文献信息

• Rhodium(II)-catalyzed addition of 2-diazo(fluoroalkyl)acetoacetates to sulfides: a simple synthesis of stable sulfonium ylides
  作者：Shizheng Zhu、Shifa Zhu、Yuanxi Liao

  DOI：10.1016/j.jfluchem.2004.01.012

  日期：2004.7

  to the corresponding sulfonium ylides. While thianthrene gave trans-thianthrenium 5,10-di(fluoroalkylacetoethoxycarbonyl)methylides (7a and 7b) under the same reaction condition, the structure of 7btrans-thianthrenium 5,10-di(bromodifluoroacetoethoxy-carbonyl)methylides was fully confirmed by spectral methods and X-ray single crystal diffraction analysis. All the ylide products obtained are fairly stable

  2-重氮（氟烷基）乙酰乙酸酯1在催化Rh 2（OAc）4的存在下，在温和的反应条件下容易与许多硫化物反应，得到相应的。在相同反应条件下，噻吩制得反式噻吨5,10-二（氟代烷基乙氧基乙氧基羰基）甲基化物（7a和7b），而光谱法已完全证实了7b式反噻吨5,10-二（溴代二氟乙酰乙氧基羰基）甲基化物的结构。和X射线单晶衍射分析。由于氟原子具有很强的吸电子性能，因此获得的所有叶立德产物都相当稳定。
• Rh2(OAc)4 catalyzed formation of fluorine-containing polysubstituted furans from diazocompounds and aromatic alkynes
  作者：Wan Pang、Shifa Zhu、Yong Xin、Huanfeng Jiang、Shizheng Zhu

  DOI：10.1016/j.tet.2009.12.015

  日期：2010.2

  A new building block strategy for the synthesis Of fluorine-containing 1,2,4-trisubstituted furan was reported The 1,2,4-trisubstituted furan was constructed through [3+2] cycloaddition reaction of fluoroacetyl-containing diazocompound and aromatic alkyne, catalyzed by Rh-2(OAc)(4) (C) 2009 Elsevier Ltd All rights reserved