2-(3-aminophenyl)-Δ²-oxazoline | 81187-71-5

• 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: 2-(3-aminophenyl)-Δ²-oxazoline
• 英文别名: [3-(4,5-dihydrooxazol-2-yl)phenyl]amine；3-(4,5-dihydrooxazol-2-yl)aniline；3-(4,5-dihydro-oxazol-2-yl)-aniline；3-(4,5-Dihydro-oxazol-2-yl)-anilin；2-(3-aminophenyl)oxazoline；3-(4,5-dihydro-1,3-oxazol-2-yl)aniline
• CAS: 81187-71-5
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: ZMPALKWGZDRORH-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  348.2±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  储存温度应控制在2-8°C，并请避免光线直射。

反应信息

• 作为反应物：
  描述：

  2-(3-aminophenyl)-Δ²-oxazoline 、 5-(4-chloro-phenyl)-furan-2-carbonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-(4-chlorophenyl)-N-[3-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]furan-2-carboxamide
  参考文献：
  名称：

  Discovery and Biological Evaluation of 5-Aryl-2-furfuramides, Potent and Selective Blockers of the Na_v1.8 Sodium Channel with Efficacy in Models of Neuropathic and Inflammatory Pain

  摘要：

  Na(v)1.8 (also known as PN3) is a tetrodotoxin-resistant (TTx-r) voltage-gated sodium channel (VGSC) that is highly expressed on small diameter sensory neurons and has been implicated in the pathophysiology of inflammatory and neuropathic pain. Recent studies using an Na(v)1.8 antisense oligonucleotide in an animal model of chronic pain indicated that selective blockade of Na(v)1.8 was analgesic and could provide effective analgesia with a reduction in the adverse events associated with nonselective VGSC blocking therapeutic agents. Herein, we describe the preparation and characterization of a series of 5-substituted 2-furfuramides, which are potent, voltage-dependent blockers (IC50 < 10 nM) of the human Na(v)1.8 channel. Selected derivatives, such as 7 and 27, also blocked TTx-r sodium currents in rat dorsal root ganglia (DRG) neurons with comparable potency and displayed > 100-fold selectivity versus human sodium (Na(v)1.2, Na(v)1.5, Na(v)1.7) and human ether-a-go-go (hERG) channels. Following systemic administration, compounds 7 and dose-dependently reduced neuropathic and inflammatory pain in experimental rodent models.

  DOI：

  10.1021/jm070637u
• 作为产物：
  描述：

  4,5-二氢-2-苯基恶唑 在 乙醇 、 铂 作用下， 生成 2-(3-aminophenyl)-Δ²-oxazoline
  参考文献：
  名称：

  Aminophenyl-2-oxazolines as Local Anesthetics

  摘要：

  DOI：

  10.1021/ja01290a042

文献信息

• A simple synthesis of Δ2-oxazines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles
  作者：Helmut Vorbrüggen、Konrad Krolikiewicz

  DOI：10.1016/0040-4020(93)80021-k

  日期：1993.1

  Carboxylic acids react readily at O°→+24°C with amino alcohols, amino mercaptans and o-aminophenols in the presence of triphenylphosphine- or tributylphosphine dichloride (generated from the reaction of the phosphines with hexachloroethane or CCl4) and triethylamine in acetonitrile to form the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and 2-substituted benzoxazoles in reaction step in

  羧酸在三苯基膦或三丁基膦二氯化物（由膦与六氯乙烷或CCl 4的反应生成）和三乙胺在乙腈中的存在下，于0°→+ 24°C易与氨基醇，氨基硫醇和邻氨基酚反应形成相应的Δ 2个-oxazolines，Δ 2个-oxazines，Δ 2 -thiazolines和在2-取代苯并恶唑在高达80％的产率反应步骤。
• S–Co(II) cascade catalysis: cyclocondensation of aromatic nitriles with alkamine
  作者：Haixia Ge、Ping Liu、Xiangnan Li、Wei Sun、Jianli Li、Bingqin Yang、Zhen Shi

  DOI：10.1016/j.tet.2013.05.132

  日期：2013.8

  A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent

  在热和微波条件下，已成功开发了无溶剂的S / Co（NO 3）2芳族腈与3-氨基-1-丙醇或2-氨基乙醇的级联催化环缩合反应。通过这种两组分方案，可以以良好至极佳的收率和较短的反应时间选择性地合成单-和双-恶嗪和恶唑啉。该催化系统具有出色的化学选择性，可以重复使用至少7次，而不会在后续反应中显着降低活性。
• A simple synthesis of Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and Δ2-imidazolines
  作者：Helmut Vorbrüggen、Konrad Krolikiewicz

  DOI：10.1016/s0040-4039(01)93017-5

  日期：1981.1

  acids react with amino alcohols, amino mercaptans or diamines in the presence of triphenylphosphine, CCl4 and tert. bases to afford in 50–75% yield the corresponding Δ2-oxazolines, Δ2-oxazines, Δ2-thiazolines and Δ2-imidazolines.

  羧酸在三苯基膦，CCl 4和叔胺的存在下与氨基醇，氨基硫醇或二胺反应。个碱基至50-75％得到得到相应的Δ 2个-oxazolines，Δ 2个-oxazines，Δ 2 -thiazolines和Δ 2个-imidazolines。
• Oxazoline or oxazine acetoacetate aqueous coating compositions
  申请人：S. C. Johnson Commercial Markets, Inc.

  公开号：US06235901B1

  公开（公告）日：2001-05-22

  A novel compound having the formula: wherein R is an alkyl group containing 1-5 carbon atoms or an aryl, substituted aryl, substituted or unsubstituted heteroaryl, alkyl-aryl, alkylether-aryl or O; R1 and R2 are hydrogen or a methyl group; X is O, NH, NR′ wherein R′ is an alkyl group containing 1-5 carbon atoms, or O—R″ or NR″ wherein O—R″ is O-alkyl-O or O-alkyl, NR″ is O-alkyl-ONH, wherein each instance alkyl contains 1-5 carbon atoms and n is 0 or 1. The compound of this invention is useful as a monomer which can be polymerized and/or copolymerized by catonic polymerization. Polymers and copolymers produced in this invention can be crosslinked and are useful in coatings, inks, overprint varnishes, and surface treatment applications.

  一种新的化合物，其化学式为：其中R是含有1-5个碳原子的烷基或芳基，取代的芳基，取代或未取代的杂环芳基，烷基芳基，烷基醚芳基或O; R1和R2是氢或甲基基团; X是O、NH、NR′（其中R′是含有1-5个碳原子的烷基），或O-R″或NR″（其中O-R″是O-烷基-O或O-烷基，NR″是O-烷基-ONH，其中每个烷基都含有1-5个碳原子，n为0或1。本发明的化合物可用作可以通过阳离子聚合进行聚合和/或共聚合的单体。在本发明中生产的聚合物和共聚物可以交联，并且可用于涂料、油墨、印刷油漆和表面处理应用中。
• Aminophenyl-oxazolines
  申请人：ABBOTT LAB

  公开号：US02114326A1

  公开（公告）日：1938-04-19