(S)-benzyl 4-hydroxy-1-phenylbutan-2-ylcarbamate | 200267-80-7

• 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: (S)-benzyl 4-hydroxy-1-phenylbutan-2-ylcarbamate
• 英文别名: benzyl N-[(2S)-4-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 200267-80-7
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: VAFVBSLCFMPTKA-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 4-hydroxy-1-phenylbutan-2-ylcarbamate 在 过甲酸 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 甲酸 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-amino-4-phenylbutane-1-sulfonic acid
  参考文献：
  名称：

  Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

  摘要：

  Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.098
• 作为产物：
  描述：

  silver benzoate 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 6.67h， 生成 (S)-benzyl 4-hydroxy-1-phenylbutan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

  摘要：

  Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.098

文献信息

• Synthesis and Evaluation of Chirally Defined Side Chain Variants of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance in Malaria Chemotherapy
  作者：Vasantha Rao Dola、Awakash Soni、Pooja Agarwal、Hafsa Ahmad、Kanumuri Siva Rama Raju、Mamunur Rashid、Muhammad Wahajuddin、Kumkum Srivastava、W. Haq、A. K. Dwivedi、S. K. Puri、S. B. Katti

  DOI：10.1128/aac.01152-16

  日期：2017.3

  A novel 4-aminoquinoline derivative [( S )-7-chloro- N -(4-methyl-1-(4-methylpiperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

  摘要 一种新型 4-氨基喹啉衍生物 [( S )-7-氯- N -(4-甲基-1-(4-甲基哌嗪-1-基)戊烷-2-基)-喹啉-4-胺三磷酸酯]对耐氯喹的疟原虫具有治疗活性，已被确定作为血吸虫杀灭剂进行临床前开发。经过详细的结构-活性关系（SAR）研究后选出的先导分子具有良好的固态特性，对 体外 和 体内 实验疟疾模型具有良好的活性。体外 体外 吸收、分布、代谢和排泄（ADME）参数表明其具有良好的类药物特征。
• Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis
  作者：Simon B. Davies、M.Anthony McKervey

  DOI：10.1016/s0040-4039(98)02573-8

  日期：1999.2

  N-Z-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniie, (S)-(−)-coniceine and a pipecoline precursor is described.

  源自非外消旋β-氨基酸的N - Z -γ-氨基醇在乙腈中被二氧化锰平滑氧化，得到醛，这些醛可在Wittig反应中与羰基取代的磷烷原位捕获。描述了该方法在生物碱（S）-（+）- N -BOC-coniie，（S）-（-）-coniceine和胡椒碱前体的合成中的应用。