2,2,3,4,4-五氟-4-(1,1,2,2,3,3-六氟-3-三氟甲氧基丙氧基)丁酸 | 919005-27-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,2,3,4,4-五氟-4-(1,1,2,2,3,3-六氟-3-三氟甲氧基丙氧基)丁酸
• 英文名称: 2,2,3,4,4-pentafluoro-4-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxypropoxy)butyric acid
• 英文别名: 2,2,3,4,4-pentafluoro-4-[1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propoxy]butanoic acid；2,2,3,4,4-pentafluoro-4-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-butyric acid；2,2,3,4,4-Pentafluoro-4-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-butyric acid
• CAS: 919005-27-9
• 化学式: C₈H₂F₁₄O₄
• 分子量: 428.079
• InChiKey: KCCPNPRWYDZVOE-UHFFFAOYSA-N

物化性质

• 沸点：
  243.4±40.0 °C(Predicted)
• 密度：
  1.748±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  2,2,3,4,4-pentafluoro-4-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)butan-1-ol 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 potassium bromide 作用下， 以 水 、 乙腈 为溶剂， 以82%的产率得到2,2,3,4,4-五氟-4-(1,1,2,2,3,3-六氟-3-三氟甲氧基丙氧基)丁酸
  参考文献：
  名称：

  TEMPO mediated oxidation of fluorinated alcohols to carboxylic acids

  摘要：

  Fluorinated carboxylic acids (3a-f) have been prepared in good yield by oxidizing the corresponding alcohols (2a-f) in the presence of TEMPO (1) as catalyst, using oxidants like bleach and oxygen. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.002

文献信息

• [EN] METHOD OF PREPARING HIGHLY FLUORINATED CARBOXYLIC ACIDS AND THEIR SALTS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDES CARBOXYLIQUES HAUTEMENT FLUORÉS ET DE LEURS SELS
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2011066156A1

  公开（公告）日：2011-06-03

  A method for preparing highly fluorinated carboxylic acids and theirs salts and the precursors thereof comprising subjecting a highly fluorinated olefin of the general formula (I) : Rf(O)n-(CF2)m-CF=CF2 to a derivative of formic acid according to the general formula (II) HCOR in the presence of a radical initiator to form carboxylic acid precursor in the form of an O-ester, S-ester or an amide adduct of the general formula (III) and hydrolysing the adduct of formula (III) Rf-On-(CF2)m-CFH-CF2-COR to form the carboxylic acid or its salt of the general formula (IV) RfOn-(CF2)m-CFH-CF2-COO-M+ wherein in formulae (II) and (III) R represents a residue O-M+, S-M+, OR`, SR' or NR`R`` wherein R' and R'' are independent of each other linear or branched or cyclic aliphatic or aromatic residues that contain at least one carbon atom and that do not have an alpha-H-atom and Rf represents H or a perfluorinated or partially fluorinated, linear, branched, aliphatic or aromatic, carbon atoms containing residue or hydrogen, n is 1 or 0, m represents an integer between 0 and 6 and M+ represents a cation including H+.

  一种制备高度氟化羧酸及其盐和前体的方法，包括将通式（I）的高度氟化烯烃：Rf（O）n-（CF2）m-CF=CF2与通式（II）的甲酸衍生物在自由基引发剂的存在下反应，形成羧酸前体，其形式为通式（III）的O-酯，S-酯或酰胺加合物，并水解式（III）的加合物Rf-On-（CF2）m-CFH-CF2-COR，形成通式（IV）的羧酸或其盐：RfOn-（CF2）m-CFH-CF2-COO-M+，其中在式（II）和（III）中，R代表残基O-M+，S-M+，OR'，SR'或NR'R''，其中R'和R''独立于彼此，是线性或支链或环状的脂肪族或芳香族残基，其中至少含有一个碳原子，且不具有α-H-原子，Rf代表H或全氟化或部分氟化的线性，支链，脂肪族或芳香族，含碳原子的残基或氢，n为1或0，m代表0至6之间的整数，M+代表包括H+的阳离子。
• METHODS OF PREPARING FLUORINATED CARBOXYLIC ACIDS AND THEIR SALTS
  申请人：Hintzer Klaus

  公开号：US20120184770A1

  公开（公告）日：2012-07-19

  A method for preparing fluorinated carboxylic acids and theirs salts is described comprising subjecting a fluorinated alcohol of the general formula (A): A-CH 2 —OH to at least one first and at least one second oxidizing agent to produce a highly fluorinated carboxylic acid or their salts of the general formula (B): A-COO M + , wherein M+ represents a cation and wherein A in formulas (A) and (B) is the same and A represents the residue: Rf-[0] p -CX″Y″-[0] m -CX′Y′-[0] n -CXY— wherein Rf represents a fluorinated alkyl residue which may or may not contain one or more catenary oxygen atoms, p, m and n are independently from each other either 1 or O, X, X′, X″, Y, Y′ and Y″ are independently from each other H, F, CF 3 , or C 2 F 5 with the proviso that not all of X, X′, X″, Y, Y′ and Y″ are H; or A represents the residue: R—CFX— wherein X and R are independently selected from a hydrogen, a halogen, or an alkyl, alkenyl, cycloalkyl, or aryl residue, which may or may not contain one or more fluorine atoms and which may or may not contain one or more catenary oxygen atoms; wherein said at least one first oxidizing agent is a compound that can be converted, by action of the second oxidizing agent, into a reactive species capable of oxidizing the fluorinated alcohol.

  本发明涉及一种制备氟代羧酸及其盐的方法，包括将通式（A）的氟代醇A-CH2-OH经过至少一种第一氧化剂和至少一种第二氧化剂处理，以产生通式（B）的高度氟化的羧酸或其盐，其中M+代表阳离子，A在式（A）和（B）中相同，A代表残基：Rf-[0]p-CX″Y″-[0]m-CX′Y′-[0]n-CXY—，其中Rf代表可能含有一个或多个链氧原子的氟代烷基残基，p、m和n彼此独立，均为1或O，X、X′、X″、Y、Y′和Y″彼此独立，为H、F、CF3或C2F5，但不是所有的X、X′、X″、Y、Y′和Y″都是H；或者A代表残基：R—CFX—，其中X和R独立选择氢、卤素或含有一个或多个氟原子和一个或多个链氧原子的烷基、烯基、环烷基或芳基残基。其中，所述至少一种第一氧化剂是一种化合物，可以通过第二氧化剂的作用转化为能够氧化氟代醇的反应性物种。
• Methods of preparing fluorinated carboxylic acids and their salts
  申请人：Hintzer Klaus

  公开号：US08809580B2

  公开（公告）日：2014-08-19

  A method for preparing fluorinated carboxylic acids and theirs salts is described comprising subjecting a fluorinated to at least one first and at least one second oxidizing agent to produce a highly fluorinated carboxylic acid or their salts. The first oxidizing agent is a compound that can be converted, by action of the second oxidizing agent, into a reactive species capable of oxidizing the fluorinated alcohol.

  本发明涉及一种制备氟代羧酸及其盐的方法，包括将氟代化合物暴露于至少一种第一氧化剂和至少一种第二氧化剂中，以产生高度氟代羧酸或其盐。第一氧化剂是一种化合物，可通过第二氧化剂的作用转化为能够氧化氟代醇的反应性物种。
• [EN] METHODS OF PREPARING FLUORINATED CARBOXYLIC ACIDS AND THEIR SALTS<br/>[FR] PROCÉDÉS DE PRÉPARATION D'ACIDES CARBOXYLIQUES FLUORÉS ET DE LEURS SELS
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2011050131A3

  公开（公告）日：2011-08-25
• METHOD OF PREPARING HIGHLY FLUORINATED CARBOXYLIC ACIDS AND THEIR SALTS
  申请人：3M Innovative Properties Company

  公开号：EP2504306B1

  公开（公告）日：2016-12-21