4-hydroxyphenyl N-tert-butylnitrone | 93376-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxyphenyl N-tert-butylnitrone
• 英文别名: (Z)-N-(4-hydroxybenzylidene)-2-methylpropan-2-amine oxide；α-(Z)-(4-hydroxyphenyl)-N-tert-butylnitrone；N-tert-butyl α-(4-hydroxyphenyl) nitrone；tert-butyl(4-hydroxybenzylidene)amine-N-oxide；C-(4-hydroxyphenyl)-N-tert-butylnitrone
• CAS: 93376-44-4；137957-43-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: PSYHRZCRICXGJJ-WQLSENKSSA-N

物化性质

• 沸点：
  340.6±44.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲基自由基 、 4-hydroxyphenyl N-tert-butylnitrone 以 水 为溶剂， 生成
  参考文献：
  名称：

  高静压会改变溶液中的自旋俘获率。取决于硝酮自旋阱的结构。

  摘要：

  使用竞争性自旋俘获方法，对各种短寿命自由基（甲基，乙基和苯基）的相对自旋俘获速率进行了定量。通过使用高压电子自旋共振（ESR）设备，将高静压应用于竞争性自旋捕集系统。在高压（490 bar）下，烷基和苯基自由基的自旋俘获速率常数增加了10％至40％，并且该增加取决于硝酮自旋阱的结构。当叔丁基（4-吡啶基亚甲基）胺N-氧化物（4-POBN）用作自旋阱时，可获得最大的增加。对于四个POBN系统，两个自旋捕获反应的激活体积（DeltaDeltaV（双匕首））计算为-17-（-9）cm（3）mol（-1）。

  DOI：

  10.1039/b515682c
• 作为产物：
  描述：

  N-叔丁基羟胺盐酸盐 、 对羟基苯甲醛 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以35%的产率得到4-hydroxyphenyl N-tert-butylnitrone
  参考文献：
  名称：

  Microwave-assisted synthesis of hydroxyphenyl nitrones with protective action against oxidative stress

  摘要：

  Oxidative stress plays an important role in neuronal death in neurodegenerative disorders such as Parkinson's disease (PD). Hydroxyphenyl nitrones, derivatives of the nitrone spin trap alpha-phenyl-N-tert-butylnitrone (PBN), were synthesized and their antioxidant, anti-inflammatory and neuroprotective activity in neural cells evaluated. These hydroxyphenyl nitrones 5-7 were synthesized by reaction of the corresponding hydroxybenzaldehyde with N-tert-butyl hydroxylamine under microwave irradiation. They showed good peroxyl free radical scavenger capacities, analyzed by oxygen radical absorbance capacity (ORAC). Also inhibited peroxynitrite-mediated tyrosine nitration of alpha-synuclein in vitro and protected human neuroblastoma (SH-SY5Y) cells against SIN-1 and 6-OHDA toxicity when micromolar concentrations were used. Besides, the hydroxyphenyl nitrones evaluated showed anti-inflammatory activity modulating nitrite production in primary neural cell cultures of astrocytes and microglia treated with lipopolysaccharide (LPS), a potent inflammatory agent. These experimental data suggest a potential therapeutic use of these hydroxyphenyl nitrones against oxygen and nitrogen reactive species involved in neurodegenerative pathology. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.044

文献信息

• Iridium(III)-Catalyzed C–H Amidation of Nitrones with Dioxazolones
  作者：Xia Mi、Weisheng Feng、Chao Pi、Xiuling Cui

  DOI：10.1021/acs.joc.9b00300

  日期：2019.5.3

  efficiently achieved through Ir(III)-catalyzed direct C–H amidation of nitrones with good to excellent yields and tolerance of broad functional groups. This reaction smoothly proceeded at room temperature in the absence of acid or base in a short reaction time. Carbon dioxide was generated as the sole byproduct, thus providing an environmentally benign amidation process. The title products could be efficiently

  通过Ir（III）催化的硝基甲烷的直接C–H酰胺化反应，可以高效地获得各种酰胺化的硝酮，并具有良好至优异的收率和宽泛的官能团耐受性。该反应在短时间内在室温下在不存在酸或碱的条件下平稳地进行。产生二氧化碳作为唯一的副产物，因此提供了对环境无害的酰胺化过程。标题产物可以有效地转化为取代的苯并异恶唑啉。
• NITRONE COMPOUNDS AND THEIR USE IN PERSONAL CARE
  申请人：Dow Global Technologies LLC

  公开号：US20150335546A1

  公开（公告）日：2015-11-26

  Provided are compounds and compositions thereof that are useful as antioxidants in personal care formulations. The compounds are of the formula I: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein.

  提供了化合物及其组合物，可作为个人护理配方中的抗氧化剂。该化合物的化学式如下：其中R、R1、R2、R3、R4、R5和R6的定义如本文所述。
• 1H and13C NMR Spectra of (Z)-C-arylN-tert-butyl nitrones
  作者：Robert W. Murray、Megh Singh

  DOI：10.1002/mrc.1260290917

  日期：1991.9

  The 1H and 13C NMR spectra of 12 (Z)‐C‐aryl N‐tert‐butyl nitrones were measured and proton and carbon assignments made. The nitrones were synthesized by the dimethyldioxirane method.

  测量了 12 (Z)-C-芳基 N-叔丁基硝酮的 1H 和 13C NMR 谱，并进行了质子和碳分配。硝酮通过二甲基二环氧乙烷法合成。
• Nitrone inhibition of oxidation of unsaturated fats
  申请人：Dow Global Technologies LLC

  公开号：US10130574B2

  公开（公告）日：2018-11-20

  Provided are compositions useful for inhibiting oxidation of unsaturated fats comprising an antioxidant compound of Formula I: wherein R, R1, R2, R3, R4, R5 and R6 are as defined herein.

  本发明提供了用于抑制不饱和脂肪氧化的组合物，其中包含式 I 的抗氧化剂化合物： 其中 R、R1、R2、R3、R4、R5 和 R6 如本文所定义。
• Nitrone inhibition of cancer development
  申请人：OKLAHOMA MEDICAL RESEARCH FOUNDATION

  公开号：US20020004531A1

  公开（公告）日：2002-01-10

  PBN (&agr;-phenyl-tert-butylnitrone), and its derivatives nitrone-based free radical traps, significantly reduce preneoplastic nodule development as well as inhibit hepatocellular carcinoma (HCC) formation at very low levels. The involvement of reactive oxygen species (ROS) in cancer development has been strongly implicated for many years. The involvement of ROS has been strongly implicated in cancer development is a model system where feeding a choline deficiency (CD) diet to rats leads to hepatocellular carcinoma (HCC) development. Administering PBN in the drinking water inhibits HCC formation. Preneoplastic nodule growth in the liver is significantly suppressed by administering PBN, or some ofits natural metabolites, in the diet. The effectiveness of PBN in preventing HCC development in the CD liver model is considered due to its prevention of tumor development after the target cells have already been initiated, i.e.genetically changed into tumor cells. Administration of PBN (or its potent derivatives) to humans that may already have microscopic tumor preneoplastic nodules should prevent the eventual frank tumor formation.

  PBN（&agr;-phenyl-tert-butylnitrone，苯基叔丁基硝酮）及其衍生物硝基自由基捕获剂可显著减少肿瘤前结节的发展，并在极低水平上抑制肝细胞癌（HCC）的形成。多年来，活性氧（ROS）与癌症发展的关系一直很密切。在一个模型系统中，给大鼠喂食胆碱缺乏（CD）饮食会导致肝细胞癌（HCC）的发生，ROS 与癌症的发生发展有着密切的关系。在饮用水中添加 PBN 可抑制 HCC 的形成。在饮食中添加 PBN 或其某些天然代谢物可显著抑制肝脏中肿瘤前结节的生长。在 CD 肝脏模型中，多肽萘能有效防止 HCC 的发展，这是因为多肽萘能在靶细胞已经开始生长（即基因改变为肿瘤细胞）后防止肿瘤的发展。对已经出现微小肿瘤前瘤结节的人体施用 PBN（或其强效衍生物），应能防止肿瘤最终形成。