(-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-3-chloromandelamide | 121251-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-3-chloromandelamide
• 英文别名: [(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamide；N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamide；(2S)-2-(3-chlorophenyl)-2-hydroxy-N-[(2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide
• CAS: 121251-86-3
• 化学式: C₁₈H₁₈ClNO₃
• 分子量: 331.799
• InChiKey: KEQMMBZHOCRYBI-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-3-chloromandelamide 在 dimethyl sulfide borane 、 TEA 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 [(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethyl]-((S)-7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7
• 作为产物：
  描述：

  2-氨基-7-甲氧基四氢萘 在 ammonium hydroxide 、 TEA 、 氢溴酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-3-chloromandelamide
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7

文献信息

• Process for the O-alkylation of N-(hydroxy)aralkylphenylethanolamines
  申请人：Sanofi

  公开号：US04927955A1

  公开（公告）日：1990-05-22

  A process for the preparation of a compound of formula ##STR1## wherein X represents hydrogen, halogen, trifluoromethyl or lower alkyl group; W represents methyl, Q represents hydrogen or W and Q, together, form an ethylene group and R' represents a lower alkyl group which comprises protecting the amino group of the phenol corresponding to the compound of formula I, submitting the compound thus obtained to an alkylation (with a compound of formula Hal--CH.sub.2 --COOR', wherein R' is as defined hereinabove for the formula I and Hal is chlorine, bromine or iodine) and then releasing the amino group of the product thus obtained.

  一种制备公式##STR1##中化合物的方法，其中X代表氢、卤素、三氟甲基或较低的烷基；W代表甲基，Q代表氢或W和Q一起形成乙烯基，R'代表较低的烷基，该方法包括保护与公式I相应的苯酚的氨基，将所得化合物进行烷基化（使用公式Hal--CH.sub.2 --COOR'的化合物进行烷基化，其中R'如上述公式I所定义，Hal是氯、溴或碘），然后释放所得产物的氨基基团。
• (RR) and (RS stereoisomers of
  申请人：Sanofi

  公开号：US05347037A1

  公开（公告）日：1994-09-13

  A process for the preparation of a compound of formula (I) ##STR1## which is a (RR) and (RS) stereoisomer of N-(7-ethoxycarbonylmethoxy-1,2,3,4,-tetrahydronaphth-2-yl)-2-(3-chlorophen yl)-2-hydroxyethanamine and their pharmaceutically acceptable salts.

  一种制备式（I）的化合物的方法，式中化合物为N-（7-乙氧羰基甲氧基-1,2,3,4-四氢萘-2-基）-2-（3-氯苯基）-2-羟基乙胺的（RR）和（RS）立体异构体及其药学上可接受的盐。
• Procédé pour la préparation de phényléthanolaminotétralines
  申请人：ELF SANOFI

  公开号：EP0303545B1

  公开（公告）日：1992-06-17
• Procédé pour la O-alkylation de N-(hydroxy)aralkylphényléthanolamines
  申请人：SANOFI

  公开号：EP0303546B1

  公开（公告）日：1994-12-28
• US4927955A
  申请人：——

  公开号：US4927955A

  公开（公告）日：1990-05-22