(R)-N-(2-(o-methoxyphenoxy)-1-methylethyl)-phthalimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (R)-N-(2-(o-methoxyphenoxy)-1-methylethyl)-phthalimide
• 英文别名: 2-[(2R)-1-(2-methoxyphenoxy)propan-2-yl]isoindole-1,3-dione
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: XMSWTXSKQQKIHJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-(2-(o-methoxyphenoxy)-1-methylethyl)-phthalimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 以98.1%的产率得到(R)-1-(o-methoxyphenoxy)-2-aminopropane
  参考文献：
  名称：

  Optically active isocarbostyril derivatives and a method of preparing

  摘要：

  一种新化合物的四种不同光学异构体现已提供为新物质。这四种光学异构体现命名为(2R, 1'S)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇，(2S, 1'S)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇，(2S, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇和(2R, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇。这四种光学异构体对其β-肾上腺素受体阻滞效应和α-肾上腺素受体阻滞效应具有不同活性，并且与所述异构体混合物的光学不活性消旋混合物相比，它们可用作治疗各种心血管疾病的有价值的药剂。这四种光学异构体可以通过色谱法从(1'S)-或(1'R)-N-[2'-(o-甲氧基苯氧基)-1'-甲基乙基]-5-(4"-异卡波斯蒂利氧甲基)-2-噁唑烷二酮中分离生产和分离。将其(5R, 1'S)-异构体和其(5S, 1'S)-异构体，或其(5S, 1'R)-异构体和其(5R, 1'R)-异构体分离，然后在碱性条件下水解每个分离的异构体，以分别获得(2R, 1'S)-、(2S, 1'S)-、(2S, 1'R)-和(2R, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇。

  公开号：

  US04659833A1
• 作为产物：
  描述：

  (R)-N-(2-tosyloxy-1-methylethyl)-phthalimide 生成 (R)-N-(2-(o-methoxyphenoxy)-1-methylethyl)-phthalimide
  参考文献：
  名称：

  TAKAXASI, TOSIXIRO;SUEHDA, NORIFUDZI;TSUDZI, MASAXIRO;TAXARA, JOSIYUKI;OY+

  摘要：

  DOI：

文献信息

• Optically active isocarbostyril derivatives and a method of preparing the same
  申请人：NISSHIN FLOUR MILLING CO., LTD.

  公开号：EP0165110A1

  公开（公告）日：1985-12-18

  Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"- isocarbostyriloxy)-2-propanol are now provided as new substances. These four optical isomers are now nominated as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-propanol, (2S, 1'S)-1-[2'-(o-meth- oxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methyl- ethylaminol-3-(4"-isocarbostyriloxy)-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"- isocarbostyriloxy)-2-propanol, respectively. There four optical isomers have different activities for their β-adrenergic-blocking effect and α-adrenergic-blocking effect and are expectable to be more valuable agent for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)- or (1'R-N-[2'-(o-methoxyphenoxy)-1'-methylethyl]-5-(d'-iso- carbostyriloxymethyl)-2-oxalidones to isolate either its (5R; 1'S)-isomer and its (5S, 1'S)-isomer, or its (55, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately, and then hydrolysing each of these isolated isomers under alkaline conditions to obtain separately (2R,1'S)-, (2S, 1'S)-, (2S, 1'R)-and (2R, 1'R)-1-(2'-(methoxyphenoxy)-1'-methylethylamino) -3-(4"-isocarbostyriloxy)-2-propanols.

  一种新化合物--1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇的四种不同光学异构体现作为新物质提供。这四种光学异构体现命名为 (2R，1'S)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羰基吡咯烷酮氧基)-2-丙醇、(2S，1'S)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羰基吡咯烷酮氧基)-2-丙醇、(2S，1'R)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇，以及(2R，1'R)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇。这四种光学异构体的β-肾上腺素能阻断作用和α-肾上腺素能阻断作用具有不同的活性，与上述异构体化合物的光学非活性外消旋混合物相比，有望成为治疗各种心血管疾病的更有价值的药物。这四种光学异构体可通过色谱法制备并相互分离出(1'S)-或(1'R-N-[2'-(邻甲氧基苯氧基)-1'-甲基乙基]-5-(d'-异羧基吡咯氧甲基)-2-恶唑烷酮，从而分离出其(5R；1'S)-异构体和它的(5S, 1'S)-异构体，或它的(55, 1'R)-异构体和它的(5R, 1'R)-异构体，然后在碱性条件下水解这些分离出的异构体，分别得到(2R、1'S)-、(2S，1'S)-、(2S，1'R)-和(2R，1'R)-1-(2'-(甲氧基苯氧基)-1'-甲基乙基氨基)-3-(4"-异碳酸基吡咯烷酮氧基)-2-丙醇。
• TAKAXASI, TOSIXIRO;SUEHDA, NORIFUDZI;TSUDZI, MASAXIRO;TAXARA, JOSIYUKI;OY+
  作者：TAKAXASI, TOSIXIRO、SUEHDA, NORIFUDZI、TSUDZI, MASAXIRO、TAXARA, JOSIYUKI、OY+

  DOI：——

  日期：——
• US4659833A
  申请人：——

  公开号：US4659833A

  公开（公告）日：1987-04-21
• Optically active isocarbostyril derivatives and a method of preparing
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04659833A1

  公开（公告）日：1987-04-21

  Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-p ropanol are now provided as new substances. These four optical isomers are now named as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, (2S, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, respectively. These four optical isomers have different activities for their .beta.-adrenergic-blocking effect and .alpha.-adrenergic-blocking effect and are useful as valuable agents for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)- or (1'R)-N-[2'-(o-methoxyphenoxy)-1'-methylethyl]-5-(4"-isocarbostyriloxymeth yl)-2-oxazolidones to isolate either its (5R, 1'S)-isomer and its (5S, 1'S)-isomer, or its (5S, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately and then hydrolyzing each of these isolated isomers under alkaline conditions to obtain separately (2R, 1'S)-, (2S, 1'S)-, (2S, 1'R)- and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanols.

  一种新化合物的四种不同光学异构体现已提供为新物质。这四种光学异构体现命名为(2R, 1'S)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇，(2S, 1'S)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇，(2S, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇和(2R, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇。这四种光学异构体对其β-肾上腺素受体阻滞效应和α-肾上腺素受体阻滞效应具有不同活性，并且与所述异构体混合物的光学不活性消旋混合物相比，它们可用作治疗各种心血管疾病的有价值的药剂。这四种光学异构体可以通过色谱法从(1'S)-或(1'R)-N-[2'-(o-甲氧基苯氧基)-1'-甲基乙基]-5-(4"-异卡波斯蒂利氧甲基)-2-噁唑烷二酮中分离生产和分离。将其(5R, 1'S)-异构体和其(5S, 1'S)-异构体，或其(5S, 1'R)-异构体和其(5R, 1'R)-异构体分离，然后在碱性条件下水解每个分离的异构体，以分别获得(2R, 1'S)-、(2S, 1'S)-、(2S, 1'R)-和(2R, 1'R)-1-[2'-(o-甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异卡波斯蒂利氧基)-2-丙醇。