1-[3,5-双(三氟甲基)苯基]戊-1-酮 | 30071-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[3,5-双(三氟甲基)苯基]戊-1-酮
• 英文名称: 1-(3,5-bis(trifluoromethyl)phenyl)pentan-1-one
• 英文别名: 3,5-bis(trifluoromethyl)phenyl n-butyl ketone；1-[3,5-Bis(trifluoromethyl)phenyl]pentan-1-one
• CAS: 30071-94-4
• 化学式: C₁₃H₁₂F₆O
• 分子量: 298.228
• InChiKey: JPABTPNXCBHZNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[3,5-双(三氟甲基)苯基]戊-1-酮 、 4-丁基苯硼酸频呢醇酯 在 [Rh(OH)(cod)]2 、 1,3-bis(2,6-dibenzhydryl-4-methylphenyl)-1H-imidazol-3-ium chloride 、 potassium tert-butylate 、 水 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 以94 %的产率得到1-(4-butylphenyl)pentan-1-one
  参考文献：
  名称：

  通过无应变 C−C 键的激活实现简单酮的无基形式铃木-宫浦偶联

  摘要：

  基于无应变 C-C 键的活化，在简单酮和芳基硼酸酯之间建立了 Rh 催化的无导向基团形式 Suzuki-Miyaura 偶联反应。该反应成功的关键是一个亲核加成/β-碳消除序列，它可以在没有导向基团帮助的情况下激活未应变的酮羰基 C-C 键。

  DOI：

  10.1002/anie.202211080
• 作为产物：
  描述：

  C₁₃H₁₄F₆O 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以71 %的产率得到1-[3,5-双(三氟甲基)苯基]戊-1-酮
  参考文献：
  名称：

  通过无应变 C−C 键的激活实现简单酮的无基形式铃木-宫浦偶联

  摘要：

  基于无应变 C-C 键的活化，在简单酮和芳基硼酸酯之间建立了 Rh 催化的无导向基团形式 Suzuki-Miyaura 偶联反应。该反应成功的关键是一个亲核加成/β-碳消除序列，它可以在没有导向基团帮助的情况下激活未应变的酮羰基 C-C 键。

  DOI：

  10.1002/anie.202211080

文献信息

• [EN] OPTICALLY ACTIVE 1-(FLUORO-,TRIFLUOROMETHYL-OR TRIFLUOROMETHOXY-SUBSTITUTED PHENYL)ALKYLAMINE N-MONOALKYL DERIVATIVES AND PROCESS FOR PRODUCING SAME<br/>[FR] DERIVES DE 1-( PHENYLE A SUBSTITUTION FLUORO,TRIFLUOROMETHYLE OU TRIFLUOROMETHOXY)ALKYLAMINE N-MONOALKYLE OPTIQUEMENT ACTIFS ET LEUR PROCEDE DE PRODUCTION
  申请人：CENTRAL GLASS CO LTD

  公开号：WO2004022521A1

  公开（公告）日：2004-03-18

  An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula [4] is produced by a process including (a) reacting an optically active secondary amine, represented by the formula [1], with an alkylation agent R2-X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula [3]; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative,wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1 and R2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.

  通过以下过程制备一种光学活性的1-(氟代、三氟甲基或三氟甲氧基取代的苯基)烷基胺N-单烷基衍生物，其化学式如下[4]：(a) 用碱存在下，将光学活性的二级胺（化学式[1]表示）与烷基化剂R2-X反应，从而将二级胺转化为光学活性的三级胺（化学式[3]表示）；(b) 将三级胺进行氢解作用，从而生成N-单烷基衍生物，其中R代表氟原子、三氟甲基基团或三氟甲氧基团，n代表1至5之间的整数，R1和R2分别代表具有1至6个碳原子的烷基基团，Me代表甲基基团，Ar代表苯基或1-或2-萘基，*代表一个手性碳，X代表一个离去基团。
• Optically active 1-(fluoro-, trifluoromethyl-or trifluoromethoxy-substituted phenyl) alkylamine n-monoalkyl derivatives and process for producing same
  申请人：——

  公开号：US20040235961A1

  公开（公告）日：2004-11-25

  An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R 2 —X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, 1 wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R 1 and R 2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.

  以式 4 为代表的光学活性 1-(氟、三氟甲基或三氟甲氧基取代苯基)烷基胺 N-单 烷基衍生物的制备方法包括 (a) 式 1 所代表的光学活性仲胺与烷基化剂 R 2 -X，在碱存在下反应，从而将仲胺转化为由式 3 表示的光学活性叔胺；以及 (b) 将叔胺进行氢解，从而生成 N-单烷基衍生物、 1 其中 R 代表氟原子、三氟甲基或三氟甲氧基，n 代表 1 至 5 的整数，每个 R 1 和 R 2 分别代表碳原子数为 1 至 6 的烷基，Me 代表甲基，Ar 代表苯基或 1 或 2-萘基，* 代表手性碳，X 代表离去基团。
• Methyl and -alkyl ketones from carboxylic acid chlorides and organocopper reagents
  作者：G.H. Posner、C.E. Whitten

  DOI：10.1016/s0040-4039(00)89398-3

  日期：1970.1
• OPTICALLY ACTIVE 1-(FLUORO-,TRIFLUOROMETHYL-OR TRIFLUOROMETHOXY-SUBSTITUTED PHENYL)ALKYLAMINE N-MONOALKYL DERIVATIVES AND PROCESS FOR PRODUCING SAME
  申请人：Central Glass Company, Limited

  公开号：EP1530562A1

  公开（公告）日：2005-05-18
• Optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy- substituted phenyl)alkylamine N-monoalkyl derivatives and process for producing same
  申请人：Ishii Akihiro

  公开号：US20070142670A1

  公开（公告）日：2007-06-21

  An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R 2 —X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative, wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R 1 and R 2 independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.