(4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene | 159750-01-3

• 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: (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene
• 英文别名: (S)-4-benzyl-3-(3-(4-chlorophenyl)propanoyl)oxazolidin-2-one；(4S)-4-benzyl-3-[3-(4-chlorophenyl)propanoyl]-1,3-oxazolidin-2-one
• CAS: 159750-01-3
• 化学式: C₁₉H₁₈ClNO₃
• 分子量: 343.81
• InChiKey: SAVPPRKCTXPXRO-KRWDZBQOSA-N

物化性质

• 沸点：
  526.2±33.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 9.53h， 生成 BOC-L-4-氯苯丙氨酸
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009
• 作为产物：
  描述：

  对氯肉桂酸 在 palladium on activated charcoal 正丁基锂 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.33h， 生成 (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009

文献信息

• HYDROXAMIC ACIDS COMPRISING PYRAZOLE MOIETY AND USES THEREOF
  申请人：HAWAII BIOTECH, INC.

  公开号：US20200399223A1

  公开（公告）日：2020-12-24

  Compounds of Formula I are provided: R 1 is —OR 5 , m is an integer from 0 to 5, n is an integer from 0 to 2, each R 2 is independently selected from hydrogen, halogen, and alkyl, R 3 is selected from hydrogen, alkyl, cycloalkyl, aryl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkyloxyalkyl, aralkyl, alkylaminoalkyl, dialkylaminoalkyl, aralkylaminoalkyl, and heterocycloalkyl, R 5 is an alkyl, each R 4 is independently hydrogen or alkyl, and each of R 2 , R 3 , R 4 , and R 5 is independently optionally substituted. Compounds of Formula I are included in pharmaceutical compositions for the treatment of a subject exposed to a botulinum toxin.

  提供了化学式I的化合物： R1为—OR5，m为0到5之间的整数，n为0到2之间的整数，每个R2独立地选自氢、卤素和烷基，R3选自氢、烷基、环烷基、芳基、羟基烷基、烷氧基烷基、芳氧基烷基、芳基氧基烷基、芳基烷基、烷基氨基烷基、二烷基氨基烷基、芳基氨基烷基和杂环烷基，R5为烷基，每个R4独立地为氢或烷基，且R2、R3、R4和R5中的每一个都可以独立地被取代。化学式I的化合物包括在用于治疗暴露于肉毒杆菌毒素的受试者的药物组合物中。
• Hydroxamic acids comprising pyrazole moiety and uses thereof
  申请人：HAWAII BIOTECH, INC.

  公开号：US11046652B2

  公开（公告）日：2021-06-29

  Compounds of Formula I are provided: R1 is —OR5, m is an integer from 0 to 5, n is an integer from 0 to 2, each R2 is independently selected from hydrogen, halogen, and alkyl, R3 is selected from hydrogen, alkyl, cycloalkyl, aryl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkyloxyalkyl, aralkyl, alkylaminoalkyl, dialkylaminoalkyl, aralkylaminoalkyl, and heterocycloalkyl, R5 is an alkyl, each R4 is independently hydrogen or alkyl, and each of R2, R3, R4, and R5 is independently optionally substituted. Compounds of Formula I are included in pharmaceutical compositions for the treatment of a subject exposed to a botulinum toxin.

  提供了式 I 的化合物： R1是-OR5，m是0至5的整数，n是0至2的整数，每个R2独立地选自氢、卤素和烷基，R3选自氢、烷基、环烷基、芳基、羟基烷基、烷氧基烷基、芳氧基烷基、芳氧基烷基、芳烷氧基烷基、芳烷基、烷基氨基烷基、二烷基氨基烷基、芳烷基氨基烷基和杂环烷基，R5是烷基，每个R4独立地选自氢或烷基，R2、R3、R4和R5中的每个独立地任选取代。式 I 的化合物包含在药物组合物中，用于治疗暴露于肉毒杆菌毒素的受试者。
• [EN] HYDROXAMIC ACIDS COMPRISING PYRAZOLE MOIETY AND USES THEREOF<br/>[FR] ACIDES HYDROXAMIQUES COMPRENANT UNE FRACTION PYRAZOLE ET LEURS UTILISATIONS
  申请人：HAWAII BIOTECH INC

  公开号：WO2020263995A1

  公开（公告）日：2020-12-30

  Compounds of Formula I are provided:(I) R1 is -OR5, m is an integer from 0 to 5, n is an integer from 0 to 2, each R2 is independently selected from hydrogen, halogen, and alkyl, R3 is selected from hydrogen, alkyl, cycloalkyl, aryl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkyloxyalkyl, aralkyl, alkylaminoalkyl, dialkylaminoalkyl, aralkylaminoalkyl, and heterocycloalkyl, R5 is an alkyl, each R4 is independently hydrogen or alkyl, and each of R2, R3, R4, and R5 is independently optionally substituted. Compounds of Formula I are included in pharmaceutical compositions for the treatment of a subject exposed to a botulinum toxin.
• A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00088a009

  日期：1994.5

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.