(R)-3-azido-1-phenylpropanol | 168465-69-8

• 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)-3-azido-1-phenylpropanol
• 英文别名: (R)-3-azido-1-phenylpropan-1-ol；(1R)-3-azido-1-phenylpropan-1-ol
• CAS: 168465-69-8
• 化学式: C₉H₁₁N₃O
• 分子量: 177.206
• InChiKey: LLAUTEBALZSNHB-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-azido-1-phenylpropanol 在 水 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.0h， 生成 2-[[(1R)-3-amino-1-phenylpropyl]oxy]-4-chloro-5-fluorobenzonitrile
  参考文献：
  名称：

  The discovery of novel, potent and highly selective inhibitors of inducible nitric oxide synthase (iNOS)

  摘要：

  By careful analysis of experimental X-ray ligand crystallographic protein data across several inhibitor series we have discovered a novel, potent and selective series of iNOS inhibitors exemplified by compound 8. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.061
• 作为产物：
  描述：

  (R)-(+)-3-氯-1-苯基-1-丙醇 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以99%的产率得到(R)-3-azido-1-phenylpropanol
  参考文献：
  名称：

  羟烷基叠氮化物与酮的不对称施密特反应

  摘要：

  Schmidt 反应的不对称等价物允许在对称环己酮的扩环中进行立体控制。该过程包括手性 1,2- 和 1,3- 羟烷基叠氮化物与酮在酸催化下的反应；初始反应提供亚胺醚，随后可以用碱打开。报道了对该反应的系统研究，其中酮底物、手性羟烷基叠氮化物和反应条件各不相同。选择性高达约。98:2 可用于合成取代的己内酰胺，整个过程中最多涉及 1,7-立体选择。任何一种可能的迁移碳在电子上是相同的，这一事实为研究完全由立体电子因素控制的扩环反应提供了一个不寻常的机会。

  DOI：

  10.1021/ja0348896

文献信息

• Novel use of phenylheteroakylamine derivatives
  申请人：——

  公开号：US20030158185A1

  公开（公告）日：2003-08-21

  There is disclosed the use of a compound of formula (I) wherein R 1 , R 2 , X, Y, V, W and Z are as defined in the specification, and pharmaceutically acceptable salts, enantiomers or racemates thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of nitric oxide synthase activity is beneficial. Certain novel compounds of formula (Ia) and pharmaceutically acceptable salts thereof, and enantiomers and racemates thereof are disclosed; together with processes for their preparation, compositions containing them and their use in therapy. The compounds of formulae (I) and (Ia) are inhibitors of the enzyme nitric oxide synthase and are thereby particularly useful in the treatment or prophylaxis of inflammatory disease.

  公开了使用式（I）的化合物，其中R1、R2、X、Y、V、W和Z如规范中定义，并且其药学上可接受的盐、对映体或消旋体，在制备药物时用于治疗或预防抑制一氧化氮合酶活性有益的疾病或症状。公开了式（Ia）的某些新化合物及其药学上可接受的盐，以及其对映体和消旋体；以及它们的制备方法、含有它们的组合物以及它们在治疗中的应用。式（I）和（Ia）的化合物是一氧化氮合酶酶的抑制剂，因此在治疗或预防炎症性疾病方面特别有用。
• Chemoselective asymmetric synthesis of C-3a-(3-hydroxypropyl)tetrahydropyrrolo[2,3-b]indole and C-4a-(2-aminoethyl)-tetrahydropyrano[2,3-b]indole derivatives
  作者：Sara Pellegrino、Francesca Clerici、Alessandro Contini、Samantha Leone、Tullio Pilati、Maria Luisa Gelmi

  DOI：10.1016/j.tet.2009.01.004

  日期：2009.3

  The asymmetric synthesis of new tetrahydropyrrolo[2,3-b]indole 19 and tetrahydropyrano[2,3-b]indole 20 rings, substituted in position C-3a and C-4a with a hydroxy- and an amino functionalized chain, respectively, was performed starting from the racemic spiro[cyclohexane-1,3′-indoline]-2′,4-diones 7. The enantiopure spiro oxo-azepinoindolinone (+)-10, obtained from (±)-7 by the way of an asymmetric

  新的四氢吡咯并[2,3- b ]吲哚19和四氢吡喃并[2,3- b ]吲哚20环的不对称合成，分别在C-3a和C-4a位被羟基和氨基官能化的链取代，从外消旋螺[环己烷-1,3'-二氢吲哚] -2'，4-二酮7开始。制备了通过不对称扩环从（±）-7获得的对映体螺氧基-氮杂叠氮吲哚酮（+）- 10和通过水解10得到的氨基酸（+）- 14作为关键中间体用于合成对映纯化合物（-）- 19和（-）-20。由于氨基酸14是化学衍生物制备衍生物19和20的常用中间体，因此进行了实验和计算研究，以选择性地获得这些化合物并为其形成提供机理上的合理化。
• Ring Opening and Rearrangement Reactions of Tricyclo[4.2.1.0^2,5]nonan-9-one
  作者：Thorsten Bach、Ingbert Braun、Florian Rudroff、Marko Mihovilovic

  DOI：10.1055/s-2007-990937

  日期：2007.12

  to synthesize bicyclo[4.2.0]octanes by a sequence of intramolecular copper(I)-catalyzed [2+2] photocycloaddition and subsequent fragmentation reactions. The concept was tested by subjecting the photochemically accessible tricyclo[4.2.1.0 2,5 ]nonan-9-one to four different ring-opening or rearrangement reactions, which allowed for the formation of functionalized bicyclo[4.2.0]octanes by cleavage of

  介绍了通过一系列分子内铜 (I) 催化的 [2+2] 光环加成和随后的碎裂反应合成双环 [4.2.0] 辛烷的一般概念。该概念通过对光化学可及的三环[4.2.1.0 2,5 ]nonan-9-one 进行四种不同的开环或重排反应进行测试，这允许通过裂解形成官能化的双环[4.2.0]辛烷。羰基桥。研究的所有四种方法，Haller-Bauer 裂解、Schmidt 反应、Baeyer-Villiger 氧化和铑 (II) 催化重排均适用于三环[4.2.1.0 2,5 ]nonan-9-one，但它们在方面有所不同对映选择性。酶促 Baeyer-Villiger 氧化是这些方法中最成功的，也比金属催化的 Baeyer-Villiger 氧化更成功，提供对映异构体富集的内酯，例如以 72% 的产率和 95% 的 ee。第二个最成功的方法是使用市售的铑催化剂，它以良好的总产率和适度的对映选择性（高达
• Use of phenylheteroakylamine derivatives
  申请人：Cheshire David

  公开号：US06887871B2

  公开（公告）日：2005-05-03

  There is disclosed the use of a compound of formula (I) wherein R 1 , R 2 , X, Y, V, W and Z are as defined in the specification, and pharmaceutically acceptable salts, enantiomers or racemates thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of nitric oxide synthase activity is beneficial. Certain novel compounds of formula (Ia) and pharmaceutically acceptable salts thereof, and enantiomers and racemates thereof are disclosed; together with processes for their preparation, compositions containing them and their use in therapy. The compounds of formulae (I) and (Ia) are inhibitors of the enzyme nitric oxide synthase and are thereby particularly useful in the treatment or prophylaxis of inflammatory disease.

  本发明揭示了使用化合物(I)的方法，其中R1、R2、X、Y、V、W和Z在说明书中有定义，并且其药学上可接受的盐、对映体或外消旋体，用于制造药物，用于治疗或预防抑制一氧化氮合酶活性对疾病或情况有益的疾病或情况。本发明揭示了某些新型化合物(Ia)及其药学上可接受的盐、对映体和外消旋体，以及它们的制备方法、含有它们的组合物以及它们在治疗中的应用。化合物(I)和(Ia)是一氧化氮合酶酶的抑制剂，因此在治疗或预防炎症性疾病方面特别有用。
• A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells
  作者：Narmada Muthineni、Manikanta Swamy Arnipally、Sridhar Bojja、Harshadas Mitaram Meshram、Ajay Kumar Srivastava、Bhaskar Rao Adari

  DOI：10.1016/j.molcatb.2016.10.016

  日期：2016.12

  The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalized alginate beads, catalyze the bio-reduction of prochiral ketones 1a-12a to their corresponding chiral alcohols 1b-12b in higher yields of 60-99% and.excellent optical purity 75-97%. The synthesized chiral azido alcohols 10b-12b were further subjected to hydrogenation using Palladium(Pd) nanoparticles (<= 5 nm), to obtain chiral amino alcohols 10c-12c of therapeutic importance. Thus, a simple, green and inexpensive continuous chemo-enzymatic process has been developed in the synthesis of chiral alcohols/amino alcohols to enhance the scope of the methodology towards industrial application. (C) 2016 Elsevier B.V. All rights reserved.