(R)-N-pivaloyl-p-bromo-α-phenylethylamine | 197847-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-pivaloyl-p-bromo-α-phenylethylamine
• 英文别名: N-[(1R)-1-(4-bromophenyl)ethyl]-2,2-dimethylpropanamide
• CAS: 197847-12-4
• 化学式: C₁₃H₁₈BrNO
• 分子量: 284.196
• InChiKey: ZLUNJWQJXQFSAM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-N-pivaloyl-p-bromo-α-phenylethylamine 、 苯基锂 、 聚合甲醛 、 水 在 magnesium sulfate 、 silica gel 、 正己烷 、 乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以to obtain 1.48 g (yield: 66.9%) of 5-bromo-2-{(1R)-1-[(2.2-dimethylpropanoyl)amino]-ethyl}benzyl alcohol的产率得到5-bromo-2-{(1R)-1-[(2,2-dimethylpropanoyl)amino]ethyl}benzyl alcohol
  参考文献：
  名称：

  Processes for producing 7-isoindoline-quinolonecarboxylic acid derivative and its intermediate, as well as salt of 7-isoindoline-quinolonecarboxylic acid derivative, its hydrate and composition comprising the same as active ingredient

  摘要：

  制备一种具有抗菌活性的7-异吲哚喹啉羧酸衍生物（通式［1］），以及其中间体的方法：包括在金属钯的存在下，以钯催化剂为催化剂，将异吲哚-5-硼酸或5-卤代异吲哚与二烷氧基硼烷或烷氧基二硼烷反应。

  公开号：

  US20020049328A1
• 作为产物：
  描述：

  N-[(4-bromophenyl)ethyl]-2,2-dimethylpropanamide 在 dinitrobenzamide-based chiral stationary phase 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以72 mg的产率得到(S)-N-[1-(4-bromophenyl)-ethyl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Chiral recognition in the solid state: crystallographically characterized diastereomeric co-crystals between a synthetic chiral selector (Whelk-O1) and a representative chiral analyte

  摘要：

  Designed to distinguish between the enantiomers of compounds possessing commonly occurring structural features, the chiral selector used in the chiral stationary phase (CSP) 1 (Whelk-O1) is broadly applicable. In an effort to further the understanding of the mechanism of chiral recognition with this chiral selector, both diastercomeric combinations of selector 1 and a representative analyte, the pivalamide of p-bromo-alpha-phenylethylamine, 2, were successfully co-crystallized and characterized by single crystal Xray diffraction. The crystal corresponding to the complex that is more stable in solution is consistent with our previously reported chiral recognition model. The aromatic portion of 2 is in the cleft of selector 1, displaying both face-to-face and face-to-edge pi-pi interactions as well as a hydrogen bond between the benzamide proton of the selector and the carbonyl oxygen of the analyte. For the crystal corresponding to the complex, which is less stable in solution, the aromatic portion of 2 is not in the cleft of selector 1, having approached from the opposite face of the pi-acidic dinitrobenzamide moiety so as to undergo face-to-face pi-pi and hydrogen bonding interactions. Comparisons of these structures and their relevance to enantioselective chromatography are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.027

文献信息

• Processes for producing 7-isoindolinequinolonecarboxylic derivatives and intermediates therefor, salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and composition containing the same as active ingredient
  申请人：Toyama Chemical Co., Ltd.

  公开号：US06337399B1

  公开（公告）日：2002-01-08

  This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1 represents a hydrogen atom or a carboxyl-protecting group; R2 represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4 bonds; R5 represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C—R7 in which R7 represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.

  这项发明涉及生产一种表示为通用式[1]的7-异吲哚喹喔酸衍生物的过程，该衍生物可用作抗菌剂，以及其中间体：其中R1代表氢原子或羧基保护基；R2代表取代或未取代的烷基、烯基、环烷基、芳基或杂环基；R3代表氢原子、卤原子、取代或未取代的烷基、烯基、环烷基、芳基、烷氧基或烷硫基、硝基、氰基、酰基、保护或未保护的羟基和保护或未保护或取代或未取代的氨基中至少选择一种基团；R4代表氢原子、卤原子、取代或未取代的烷基、烯基、环烷基、芳基、芳基烷基、烷氧基或烷硫基、保护或未保护的羟基或亚胺基、保护或未保护或取代或未取代的氨基、烷基亚甲基基、氧代基团和每个与R4键合的碳原子一起形成环烷基的基团中至少选择一种基团；R5代表氢原子、氨基保护基、取代或未取代的烷基、环烷基、烷基磺酰基、芳基磺酰基、酰基或芳基；R6代表氢原子、卤原子、取代或未取代的烷基、烷氧基或烷硫基、保护或未保护的羟基或氨基或硝基；A代表CH或C—R7，其中R7代表卤原子、取代或未取代的烷基、烷氧基或烷硫基或保护或未保护的羟基，以及一种7-异吲哚喹喔酸盐，其通用式为[1]，以及其水合物和包含它们作为活性成分的组合物。
• Processes for producing 7-isoindoline-quinolonecarboxylic acid derivative and its intermediate, as well as salt of 7-isoindoline-quinolonecarboxylic acid derivative, its hydrate and composition comprising the same as active ingredient
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：US20020049328A1

  公开（公告）日：2002-04-25

  Processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: 1 comprising reacting, in the presence of metallic palladium, an isoindoline-5-boronic acid, or of a 5-halogenoisoindoline, in the presence of a palladium catalyst, with a dialkoxyborane or an alkoxydiborane.

  制备一种具有抗菌活性的7-异吲哚喹啉羧酸衍生物（通式［1］），以及其中间体的方法：包括在金属钯的存在下，以钯催化剂为催化剂，将异吲哚-5-硼酸或5-卤代异吲哚与二烷氧基硼烷或烷氧基二硼烷反应。
• Processes for producing 7-isoindoline-quinolone carboxylic acid derivative and its intermediate, as well as salt of 7-isoindoline-quinolonecarboxylic acid derivative, its hydrate and composition comprising the same as active ingredient
  申请人：Ojima Katsuji

  公开号：US20050203301A1

  公开（公告）日：2005-09-15

  Process for producing a 7-bromoquinolone-carboxylic acid derivative of the following formula or its salt by reacting a 2,4-dibromo-3-hydroxybenzoic acid ester compound of the formula R 7a -x to obtain a 3-alkoxy-2,4-dibromobenzoic acid ester, subjecting the 3-alkoxy-2,4-dibromobenzoic acid ester to elimination reaction of the carboxyl-protecting group to obtain a 3-alkoxy-2,4-dibromobenzoic acid, subjecting the 3-alkoxy-2,4-dibromobenzoic acid to ketoesterification reaction to obtain a 3-alkoxy-2,4-dibromobenyolacetic acid ester, reacting the 3-alkoxy-2,4-dibromobenzoylacetic acid ester with an orthoester or an acetal, then reacting the reaction product with a compound of the formula R 2a —NH or its salt to obtain a 2-(3-alkoxy-2,4-dibromobenzoyl)-3-substituted aminoacrylic acid ester and subjecting the 2-(3-alkoxy-2,4-dibromobenzoyl)-3-substituted aminoacrylic acid ester to ring-closing reaction, and products thereof.

  通过将公式如下的2,4-二溴-3-羟基苯甲酸酯化合物R7a-x与反应，得到一种3-烷氧基-2,4-二溴苯甲酸酯；将3-烷氧基-2,4-二溴苯甲酸酯进行羧基保护基的消除反应，得到3-烷氧基-2,4-二溴苯甲酸；将3-烷氧基-2,4-二溴苯甲酸进行酮酯化反应，得到3-烷氧基-2,4-二溴苯基乙酸酯；将3-烷氧基-2,4-二溴苯基乙酸酯与正酯或缩醛反应，然后将反应产物与公式为R2a—NH或其盐的化合物反应，得到一种2-(3-烷氧基-2,4-二溴苯甲酰)-3-取代氨基丙烯酸酯；将2-(3-烷氧基-2,4-二溴苯甲酰)-3-取代氨基丙烯酸酯进行环闭合反应，得到公式如下的7-溴喹啉羧酸衍生物或其盐，以及其制备方法。
• PROCESSES FOR PRODUCING 7-ISOINDOLINE-QUINOLONECARBOXYLIC ACID DERIVATIVE AND ITS INTERMEDIATE, AS WELL AS SALT OF 7-ISOINDOLINE-QUINOLONECARBOXYLIC ACID DERIVATIVE, ITS HYDRATE AND COMPOSITION COMPRISING THE SAME AS ACTIVE INGREDIENT
  申请人：Yamada Minoru

  公开号：US20070225506A1

  公开（公告）日：2007-09-27

  Process for producing a 7-bromoquinolone-carboxylic acid derivative of the following formula or its salt by reacting a 2,4-dibromo-3-hydroxybenzoic acid ester compound of the formula R 7a - x to obtain a 3-alkoxy-2,4-dibromobenzoic acid ester, subjecting the 3-alkoxy-2,4-dibromobenzoic acid ester to elimination reaction of the carboxyl-protecting group to obtain a 3-alkoxy-2,4-dibromobenzoic acid, subjecting the 3-alkoxy-2,4-dibromobenzoic acid to ketoesterification reaction to obtain a 3-alkoxy-2,4-dibromobenyolacetic acid ester, reacting the 3-alkoxy-2,4-dibromobenzoylacetic acid ester with an orthoester or an acetal, then reacting the reaction product with a compound of the formula R 2 — NH or its salt to obtain a 2-(3-alkoxy-2,4-dibromobenzoyl)-3-substituted aminoacrylic acid ester and subjecting the 2-(3-alkoxy-2,4-dibromobenzoyl)-3-substituted aminoacrylic acid ester to ring-closing reaction, and products thereof.

  通过反应公式为R7a-x的2,4-二溴-3-羟基苯甲酸酯化合物以获得3-烷氧基-2,4-二溴苯甲酸酯，将3-烷氧基-2,4-二溴苯甲酸酯进行羧基保护基的消除反应以获得3-烷氧基-2,4-二溴苯甲酸，将3-烷氧基-2,4-二溴苯甲酸进行酮酯化反应以获得3-烷氧基-2,4-二溴苯乙酸酯，将3-烷氧基-2,4-二溴苯乙酸酯与orthoester或缩醛反应，然后将反应产物与公式为R2-NH或其盐的化合物反应以获得2-(3-烷氧基-2,4-二溴苯甲酰)-3-取代氨基丙烯酸酯，将2-(3-烷氧基-2,4-二溴苯甲酰)-3-取代氨基丙烯酸酯进行环闭合反应，从而获得以下公式或其盐的7-溴喹啉羧酸衍生物的制备方法和产物。
• PROCESSES FOR PRODUCING 7-ISOINDOLINEQUINOLONECARBOXYLIC DERIVATIVES AND INTERMEDIATES THEREFOR, SALTS OF 7-ISOINDOLINEQUINOLONECARBOXYLIC ACIDS, HYDRATES THEREOF, AND COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP1031569A1

  公开（公告）日：2000-08-30

  This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1 represents a hydrogen atom or a carboxyl-protecting group; R2 represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4 bonds; R5 represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C-R7 in which R7 represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.

  本发明涉及生产由通式[1]表示的可用作抗菌剂的7-异吲哚啉-喹啉羧酸衍生物及其中间体的工艺： 其中 R1 代表氢原子或羧基保护基团；R2 代表取代或未取代的烷基、烯基、环烷基、芳基或杂环基团；R3 代表至少一个选自氢原子、卤素原子、取代或未取代的烷基、烯基、环烷基、芳基、烷氧基或硫代烷基、硝基、氰基、酰基、受保护或未受保护的羟基和受保护或未受保护或取代或未取代的氨基的基团；R4 代表至少一个选自氢原子、卤素原子、取代或未取代的烷基、烯基、环烷基、芳基、烷氧基或烷硫基、受保护或未受保护的羟基或亚氨基、受保护或未受保护的或取代或未取代的氨基、亚烷基、氧代基团和与 R4 键合的碳原子一起形成环烷基团的基团的基团；R5 代表氢原子、氨基保护基团、取代或未取代的烷基、环烷基、烷基磺酰基、芳基磺酰基、酰基或芳基； R6 代表氢原子、卤素原子、取代或未取代的烷基、烷氧基或硫代烷基、受保护或未受保护的羟基或氨基或硝基；和 A 代表 CH 或 C-R7，其中 R7 代表卤素原子、取代或未取代的烷基、烷氧基或烷硫基或受保护或未受保护的羟基，以及通式[1]代表的 7-异吲哚啉-喹啉羧酸的盐、其水合物和包含它们作为活性成分的组合物。