2-硝基-5-哌啶基苯酚 | 157831-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-硝基-5-哌啶基苯酚
• 中文别名: 2-硝基-5-哌啶苯酚
• 英文名称: 2-nitro-5-(piperidin-1-yl)phenol
• 英文别名: 2-Nitro-5-piperidinophenol；2-nitro-5-piperidin-1-ylphenol
• CAS: 157831-75-9
• 化学式: C₁₁H₁₄N₂O₃
• mdl: MFCD00052663
• 分子量: 222.244
• InChiKey: DDKAQSBPHIORAR-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70°C
• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-硝基-5-哌啶基苯酚 在 palladium complexed dendrimer 、 potassium carbonate 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 20.0~80.0 ℃ 、689.47 kPa 条件下， 反应 44.0h， 生成 3-(1-piperidinyl)-6H-dibenz[b,f][1,4]oxazocin-11(12H)-one
  参考文献：
  名称：

  与可回收钯络合树枝状大分子在二氧化硅上的分子内羰基化反应：合成含氧、氮或硫的中环稠合杂环

  摘要：

  负载在二氧化硅上的钯络合树枝状大分子被评估为分子内羰基化反应的催化剂。结果表明，树枝状催化剂显示出高活性，以优异的产率提供含氧、氮或硫的七元或八元环稠合杂环。此外，这些催化剂具有竞争优势，因为它们可以通过在空气中简单过滤而轻松回收，并可重复使用多达 8 个循环，而活性仅有轻微损失。

  DOI：

  10.1021/ja053650h
• 作为产物：
  描述：

  哌啶 、 5-氟-2-硝基苯酚 反应 14.0h， 以54%的产率得到2-硝基-5-哌啶基苯酚
  参考文献：
  名称：

  Barlin, Gordon B.; Ireland, Stephen J.; Nguyen, Trang M. T., Australian Journal of Chemistry, 1994, vol. 47, # 6, p. 1143 - 1154

  摘要：

  DOI：

文献信息

• A mild and metal-free synthesis of chiral 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazines
  作者：Hongyi Zhao、Shengnan Li、Shihao Cheng、Ziyun Lin、Dongfeng Zhang、Haihong Huang

  DOI：10.1016/j.tet.2021.132304

  日期：2021.7

  Various functionalized enantiomerically pure 3-hydroxymethyl-1,4-benzoxazine derivatives, including four stereoisomers, were synthesized from chiral 2,3-epoxy-4-trityloxybutanol. The synthesis was mild and metal-free. Yields of 52%–94%, and stereoselectivities of 95% to >99% ee, were obtained. The mechanism was investigated using online Fourier-transform infrared spectroscopy. This revealed a base-promoted

  从手性 2,3-epoxy-4-trityloxybutanol 合成了各种功能化的对映体纯 3-hydroxymethyl-1,4-benzoxazine 衍生物，包括四种立体异构体。合成过程温和且不含金属。获得了 52%–94% 的产率和 95% 到 >99% ee 的立体选择性。使用在线傅里叶变换红外光谱研究了该机制。这揭示了碱促进的环化作用以原位形成三环稠合的苯并恶嗪基-恶唑烷酮中间体，然后是水解过程。该方法可以很容易地按比例缩放并以一锅法进行。通过进一步衍生形成独特的三环稠合苯并恶嗪，展示了所得手性 3-羟甲基-1,4-苯并恶嗪衍生物作为结构单元的有用性。
• Lead Optimization of Benzoxazolone Carboxamides as Orally Bioavailable and CNS Penetrant Acid Ceramidase Inhibitors
  作者：Simona Di Martino、Piero Tardia、Vincenzo Cilibrasi、Samantha Caputo、Marco Mazzonna、Debora Russo、Ilaria Penna、Natalia Realini、Natasha Margaroli、Marco Migliore、Daniela Pizzirani、Giuliana Ottonello、Sine Mandrup Bertozzi、Andrea Armirotti、Duc Nguyen、Ying Sun、Ernesto R. Bongarzone、Peter Lansbury、Min Liu、Renato Skerlj、Rita Scarpelli

  DOI：10.1021/acs.jmedchem.9b02004

  日期：2020.4.9

  Sphingolipids (SphLs) are a diverse class of molecules that are regulated by a complex network of enzymatic pathways. A disturbance in these pathways leads to lipid accumulation and initiation of several SphL-related disorders. Acid ceramidase is one of the key enzymes that regulate the metabolism of ceramides and glycosphingolipids, which are important members of the SphL family. Herein, we describe the lead optimization studies of benzoxazolone carboxamides resulting in piperidine 22m, where we demonstrated target engagement in two animal models of neuropathic lysosomal storage diseases (LSDs), Gaucher's and Krabbe's diseases. After daily intraperitoneal administration at 90 mg kg(-1), 22m significantly reduced the brain levels of the toxic lipids glucosylsphingosine (GluSph) in 4L;C* mice and galactosylsphingosine (GalSph) in Twitcher mice. We believe that 22m is a lead molecule that can be further developed for the correction of severe neurological LSDs where GluSph or GalSph play a significant role in disease pathogenesis.
• 2-Aminobenzoxazole ligands of the hepatitis C virus internal ribosome entry site
  作者：Kevin D. Rynearson、Brian Charrette、Christopher Gabriel、Jesus Moreno、Mark A. Boerneke、Sergey M. Dibrov、Thomas Hermann

  DOI：10.1016/j.bmcl.2014.05.088

  日期：2014.8

  2-Aminobenzoxazoles have been synthesized as ligands for the hepatitis C virus (HCV) internal ribosome entry site (IRES) RNA. The compounds were designed to explore the less basic benzoxazole system as a replacement for the core scaffold in previously discovered benzimidazole viral translation inhibitors. Structure-activity relationships in the target binding of substituted benzoxazole ligands were investigated. (C) 2014 Elsevier Ltd. All rights reserved.
• Barlin Gordon B., Ireland Stephen J., Nguyen Trang M. T., Kotecka Barbara+, Austral. J. Chem., 47 (1994) N 6, S 1143-1154
  作者：Barlin Gordon B., Ireland Stephen J., Nguyen Trang M. T., Kotecka Barbara+

  DOI：——

  日期：——
• ANTIBIOTIC COMPOUNDS
  申请人：DISCUVA LTD.

  公开号：US20190194179A1

  公开（公告）日：2019-06-27

  The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae .