tert-butylacetyl fluoride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: tert-butylacetyl fluoride
• 英文别名: 3,3-dimethylbutanoyl fluoride；3,3-Dimethylbutanoyl fluoride
• 化学式: C₆H₁₁FO
• 分子量: 118.151
• InChiKey: LRYPAKRVVSUOJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butylacetyl fluoride 、 苯甲醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3,3-二甲基丁酸苄酯
  参考文献：
  名称：

  Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro(aryl)-λ³-bromane

  摘要：

  Oxidation of primary aliphatic aldehydes with p-trifluoromethylphenyl(difluoro)-lambda(3)-bromane in dichloromethane at 0 degrees C afforded acid fluorides selectively In good yields, while that of aromatic aldehydes In chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.

  DOI：

  10.1021/ol202248x
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 sodium decatungstate 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以69%的产率得到tert-butylacetyl fluoride
  参考文献：
  名称：

  通过醛键的C–H键的光催化氟化 合成酰基氟†

  摘要：

  酰氟由于其独特的稳定性而成为通用的酰化剂。然而，它们的合成可能带来挑战，并且通常通过羧酸的脱氧氟化来完成。在这里，我们证明了酰氯可以直接由醛类通过C（sp 2）-H氟化反应制备，该反应涉及廉价的光催化剂脱卡酸钠和亲电氟化剂N-氟苯磺酰亚胺。这种方便的氟化策略可将脂族和芳族醛直接转化为酰化剂。

  DOI：

  10.1039/c8cc06375c

文献信息

• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE alpha-HALO-CARBONYL COMPOUNDS<br/>[FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES DE DOLLAR G(A)-HALO-CARBONYLE OPTIQUEMENT ACTIFS
  申请人：HALLAND NIS

  公开号：WO2005080298A1

  公开（公告）日：2005-09-01

  A process for the catalytic asymmetric synthesis of an optically active compound of the formula (la) or (lb): wherein R is an organic group; X is halogen; Rl and R2which may the same or different represents H, or an organic group or Rl and R2 may be bridged together forming part of a ring system; R and R2 may be bridged together forming part of a ring system; with the provisio that R and Rl are different and R2, when different from H, is attached though a carbon-carbon bond, comprising the step of reacting a compound of the formula (2): with a halogenation agent in the presence of a catalytic amount of a chiral nitrogen containing organic compound.

  一种用于催化不对称合成光学活性化合物的方法，其化学式为(la)或(lb)：其中R是有机基团；X是卤素；R1和R2可以相同也可以不同，分别代表H，或者是有机基团，或者R1和R2可以通过形成环系统的桥连接在一起；R和R2可以通过形成环系统的桥连接在一起；在R和R1不同且R2与H不同时通过碳-碳键连接时，包括以下步骤：将化合物(2)与卤化试剂在含有含有手性氮的有机化合物的催化剂量的情况下反应。
• Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations
  作者：Yi Liu、Cuihan Zhou、Meijing Jiang、Bruce A. Arndtsen

  DOI：10.1021/jacs.2c01951

  日期：2022.6.1

  We describe the development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides from aryl, heteroaryl, alkyl, and functionalized organic halides. Mechanistic analysis suggests that the reaction proceeds via the synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create

  我们描述了从芳基、杂芳基、烷基和官能化有机卤化物合成酰基氟化物的一般钯催化羰基化方法的发展。机理分析表明，反应通过Pd(0) 的可见光光激发的协同组合进行，以诱导氧化加成和配体有利的还原消除。这些共同创造了一个单向催化循环，不受一氧化碳配位的经典效应的抑制。将酰氟的催化形成与其随后的亲核反应相结合，开辟了一种以前所未有的广度进行羰基化反应的方法，包括高度官能化的含羰基产物的组装。
• CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HALO-CAR BONYL COMPOUNDS
  申请人：Cheminova A/S

  公开号：EP1716088A1

  公开（公告）日：2006-11-02
• Catalytic Asymmetric Synthesis of Optically Active Alpha-Halo-Carbonyl Compounds
  申请人：Halland Nis

  公开号：US20070276142A1

  公开（公告）日：2007-11-29

  A process for the catalytic asymmetric synthesis of an optically active compound of the formula (1a) or (1b) wherein R is an organic group; X is halogen; R 1 and R 2 which may the same or different represents H, or an organic group or R 1 and R 2 may be bridged together forming part of a ring system; R and R 2 may be bridged together forming part of a ring system; with the provisio that R and R 1 are different and R 2 , when different from H, is attached though a carbon-carbon bond, comprising the step of reacting a compound of the formula (2) with a halogenation agent in the presence of a catalytic amount of a chiral nitrogen containing organic compound.
• Oxidation of Primary Aliphatic and Aromatic Aldehydes with Difluoro(aryl)-λ³-bromane
  作者：Masahito Ochiai、Akira Yoshimura、Md. Mahbubul Hoque、Takuji Okubo、Motomichi Saito、Kazunori Miyamoto

  DOI：10.1021/ol202248x

  日期：2011.10.21

  Oxidation of primary aliphatic aldehydes with p-trifluoromethylphenyl(difluoro)-lambda(3)-bromane in dichloromethane at 0 degrees C afforded acid fluorides selectively In good yields, while that of aromatic aldehydes In chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.