(3R)-3-aminobutanenitrile | 1074021-93-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3R)-3-aminobutanenitrile
• 英文别名: (R)-3-aminobutyronitrile
• CAS: 1074021-93-4
• 化学式: C₄H₈N₂
• 分子量: 84.1209
• InChiKey: PPBSMPOYVPZOFM-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3-aminobutanenitrile 、 1-乙基-1-甲基-4-氧代哌啶-1-碘化物 以 乙醇 、 水 为溶剂， 反应 4.17h， 以97 g的产率得到(R)-3-(4-oxopiperidin-1-yl)butyronitrile
  参考文献：
  名称：

  Practical Convergent Laboratory-Scale Synthesis of a CCR5 Receptor Antagonist

  摘要：

  An efficient laboratory-scale synthesis has been developed for the selective CCR5 antagonist 1. The convergent route has a longest linear sequence of nine steps (Is steps overall), and has overall yields of 18-25%. The route has enabled the preparation of 550 g of 1.

  DOI：

  10.1021/op200259t
• 作为产物：
  描述：

  2-甲基-2-丙基[(2R)-1-氰基-2-丙基]氨基甲酸酯 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.83h， 生成 (3R)-3-aminobutanenitrile
  参考文献：
  名称：

  Practical Convergent Laboratory-Scale Synthesis of a CCR5 Receptor Antagonist

  摘要：

  An efficient laboratory-scale synthesis has been developed for the selective CCR5 antagonist 1. The convergent route has a longest linear sequence of nine steps (Is steps overall), and has overall yields of 18-25%. The route has enabled the preparation of 550 g of 1.

  DOI：

  10.1021/op200259t

文献信息

• Process Optimisation Studies and Aminonitrile Substrate Evaluation of <i>Rhodococcus erythropolis</i> SET1, A Nitrile Hydrolyzing Bacterium
  作者：Tatenda M. Mareya、Tracey M. Coady、Catherine O'Reilly、Michael Kinsella、Lee Coffey、Claire M. Lennon

  DOI：10.1002/open.202000088

  日期：2020.4

  enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo‐aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β‐aminonitriles, structural analogues of β‐hydroxynitriles was also investigated

  在具有底物3-羟基丁腈的腈水解红球菌SET1的腈水解反应中，完成了一系列全面的优化研究，包括pH，溶剂和温度。这些确定的温度为25°C，pH为7是保留对映选择性和活性的最佳条件。还确定了向有机转化混合物中添加有机溶剂的效果。研究结果表明，SET1仅适用于特定比例的所选有机水性介质。带有未保护和受保护的β-氨基腈（β的结构类似物）的分离物的官能团耐受性羟基腈的分离收率和选择性也很差，令人失望。分离物进一步用产生极佳收率和ee（> 99％（S）–异构体，收率50％）的α-氨基腈苯基甘氨腈生成酸进行评估。用该底物进行的一系列pH研究表明，pH 7是避免产物和底物降解的最佳p​​H。
• GLYOXAMIDE SUBSTITUTED PYRROLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICAMENTS FOR THE TREATMENT OF HEPATITIS B
  申请人：Janssen Sciences Ireland UC

  公开号：US20160176817A1

  公开（公告）日：2016-06-23

  Inhibitors of HBV replication of Formula (IA) including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein X and R 1 to R 6 have the meaning as defined herein. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HBV inhibitors, in HBV therapy.

  本发明涉及一种HBV复制的抑制剂Formula（IA），包括立体化学异构体形式和其盐、水合物、溶剂物，其中X和R1至R6的含义如本文所定义。本发明还涉及制备上述化合物的过程，含有它们的制药组合物及其在HBV治疗中的使用，单独或与其他HBV抑制剂结合使用。
• Design and synthesis of pyridin-2-ylmethylaminopiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication
  作者：Renato Skerlj、Gary Bridger、Yuanxi Zhou、Elyse Bourque、Ernest McEachern、Jonathan Langille、Curtis Harwig、Duane Veale、Wen Yang、Tongshong Li、Yongbao Zhu、Michael Bey、Ian Baird、Michael Sartori、Markus Metz、Renee Mosi、Kim Nelson、Veronique Bodart、Rebecca Wong、Simon Fricker、Ron Mac Farland、Dana Huskens、Dominique Schols

  DOI：10.1016/j.bmcl.2011.09.133

  日期：2011.12

  A series of CCR5 antagonists were optimized for potent inhibition of R5 HIV-1 replication in peripheral blood mononuclear cells. Compounds that met acceptable ADME criteria, selectivity, human plasma protein binding, potency shift in the presence of alpha-glycoprotein were evaluated in rat and dog pharmacokinetics. (C) 2011 Elsevier Ltd. All rights reserved.
• WO2024081311A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Practical Convergent Laboratory-Scale Synthesis of a CCR5 Receptor Antagonist
  作者：Jason B. Crawford、Gang Chen、Bryon Carpenter、Trevor Wilson、Jenny Ji、Renato T. Skerlj、Gary J. Bridger

  DOI：10.1021/op200259t

  日期：2012.1.20

  An efficient laboratory-scale synthesis has been developed for the selective CCR5 antagonist 1. The convergent route has a longest linear sequence of nine steps (Is steps overall), and has overall yields of 18-25%. The route has enabled the preparation of 550 g of 1.