2-propoxyphenyl isocyanate | 32223-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-propoxyphenyl isocyanate
• 英文别名: 2-Propyloxyphenylisozyanat；1-Isocyanato-2-propoxybenzene
• CAS: 32223-62-4
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: WBYVBEZGKXTLFG-UHFFFAOYSA-N

物化性质

• 沸点：
  258.1±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-propoxyphenyl isocyanate 在 盐酸 作用下， 以 乙醚 、 氯仿 、 异丙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 4-(4-fluorophenyl)-1-[3-(2-propoxyphenylcarbamoyloxy)-2-hydroxypropyl]piperazin-1-ium chloride
  参考文献：
  名称：

  荧光法测定苯氨基甲酸衍生物的临界胶束浓度和热力学参数

  摘要：

  1-[3-(2-烷氧基苯基氨基甲酰氧基)-2-羟丙基]-4-(4-氟苯基)哌嗪-1-氯化鎓（烷氧基=甲氧基到丙氧基；6a-c）的临界胶束浓度（CMC）值为通过使用芘作为探针在温度区间 T = 293.15–313.15 K 的荧光方法确定。CMC 对 T 的依赖性结果形成 U 形。曲线是通过使用二次多项式函数和所谓的幂律方程拟合观测值来绘制的，在 T = 298.15 K 处观察到曲线的最小值。胶束化的热力学参数，即摩尔吉布斯能量 (ΔG° )、焓 (ΔH°) 和熵 (ΔS°) 分别根据相分离模型计算。在观察之后，计算了对摩尔吉布斯能量（ΔG°）的焓（ΔH°）和熵贡献（-TΔS°）。发现焓的贡献随着温度的升高而增加，而熵的贡献在选定的温度范围内减小。最后，确定了焓熵补偿和补偿温度（Tc）。

  DOI：

  10.1007/s11696-021-01539-5
• 作为产物：
  描述：

  光气 、 2-丙氧基苯胺盐酸盐 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 2-propoxyphenyl isocyanate
  参考文献：
  名称：

  5-Hydroxytryptamine (5-HT3) receptor antagonists. 3. Ortho-substituted phenylureas

  摘要：

  A novel series of potent 5-HT3 receptor antagonists, ortho-substituted phenylureas 6a-z, is described in which the 5-membered ring of the previously reported indazoles and indolines has been replaced by an intramolecular hydrogen bond. High potency was found both for carbamate 6a and urea 6b. Granatane 6c was less potent than the equivalent tropane. Phenylurea 11c lacking the ortho substituent was inactive. Whereas further substitution could not be tolerated in the aromatic ring, activity was retained with a range of O-alkyl groups, compounds 6k-t. In addition, good activity was found for ortho ester 6u and sulfonamide 6x. The ortho-substituted phenylureas can therefore be regarded as bioisosteres of the 6,5-heterocycles indole, indazole, and indoline.

  DOI：

  10.1021/jm00169a018

文献信息

• Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides
  作者：Fridrich Gregáň、Viktor Kettmann、Pavol Novomeský、Július Sivý

  DOI：10.1135/cccc19940675

  日期：——

  The synthesis of two pairs of the title diastereomers, which represent conformationally constrained analogues of the phenylcarbamate local anesthetics, is described. The synthesis was accomplished by starting from cycloheptanone and 2-alkoxyanilines and the intermediate diastereomers of 2-aminomethylcycloalkanols (VI, VII) were separated as their 4-nitrobenzoyl derivatives (IV, V) by extraction and fractional crystallization. The prepared compounds (VIIIa, VIIIb, IXa, and IXb) are assumed to be of help in interpreting the structure activity relationships within this class of drugs.

  描述了两对标题异构体的合成，它们代表苯基氨基甲酸酯局部麻醉药的构象受限类似物。从环庚酮和2-烷氧基苯胺出发合成，通过提取和分级结晶将中间体2-氨基甲基环庚醇的异构体（VI、VII）分离为它们的4-硝基苯甲酰衍生物（IV、V）。准备的化合物（VIIIa、VIIIb、IXa和IXb）被认为有助于解释这一类药物中的结构活性关系。
• Synthesis, physico-chemical properties and bioloclical activitv of 1-(4-fluorophenvl)-4-[3-(2-,3- and 4-alkyloxyphenylcarbamoyloxy)-2-hydroxypropyl] piperaziniumchlorides
  作者：Ivan Malík、Eva Sedlárová、Jozef Csöllel、Eva Račanská、Jozef Čižmárik、Pavel Kurfürst

  DOI：10.3797/scipharm.aut-04-24

  日期：——

  1-(4-fluoropheny1)-4-[3-(2-,3- and 4-alkyloxyphenylcarbamoyloxy)-2-hydroxypropyl]piperaziniumchlorides, with one to four carbon atoms in the alkoxy group on aromatic ring have been synthesized as the derivatives of substituted phenylcarbamic acid. The structures were confirmed by their spectral data. Potential antiarrhythmic activity was evaluated in guinea-pigs model. Preliminary studies demonstrated that the evaluated compounds, using ouabain arrhythmia model, appear to possess only moderate antiarrhythmic activity. Only compound marked as 4f appears to be more potent and lead us to focus our attention on structures with more bulky substituent in the m-position at aromatic ring in the hydrophilic part of molecule.

  已經合成了具有芳香環上烷氧基組中含有一至四個碳原子的衍生物，其為1-(4-氟苯基)-4-[3-(2-,3-和4-烷氧基苯基氨基甲酰氧基)-2-羥基丙基]哌嗪銨氯化物，作為取代苯基甲酸的衍生物。通過其光譜數據確認了這些結構。在豚鼠模型中評估了潛在的抗心律失常活性。初步研究表明，在使用緩慢性心律失常模型奧巴因的評估化合物中，似乎僅具有中等抗心律失常活性。只有標記為4f的化合物似乎更有效，引導我們將注意力集中在分子的親水部分芳香環上的m-位置具有更大取代基的結構上。
• Synthesis and Characterization of Two Homologous Series of Diastereomeric 2-Alkoxyphenylcarbamates
  作者：Fridrich Gregan、Juraj Gregan、Marek Skorsepa

  DOI：10.1248/cpb.59.978

  日期：——

  stereoselective reactions. The chemical structures of these compounds were confirmed by ¹H-NMR, ¹³C-NMR and IR spectroscopy and their physico-chemical properties were characterized. The two new series of diastereomeric compounds were tested for their local anesthetic activity and parabolic relationship between the local anesthetic activity and lipophilicity was found for both cis- and trans-series.

  通过立体选择性反应合成了两个同源系列的外消旋非对映体顺式和反式（2-二甲氨基甲基环庚基）-2-烷氧基苯基氨基甲酸酯，烷基链长度范围为C 1 至C 8 。这些化合物的化学结构经 1 H-NMR、 13 C-NMR 和红外光谱证实，并对其理化性质进行了表征。测试了这两个新系列的非对映体化合物的局部麻醉活性，并发现了顺式和反式系列的局部麻醉剂活性和亲脂性之间的抛物线关系。有趣的是，顺式立体异构体表现出更高的局部麻醉活性。
• Cizmarik; Borovansky; Tumova, Pharmazie, 1987, vol. 42, # 10, p. 702 - 703
  作者：Cizmarik、Borovansky、Tumova

  DOI：——

  日期：——
• Gregan; Kettmann; Novomesky, Il Farmaco, 1993, vol. 48, # 3, p. 375 - 385
  作者：Gregan、Kettmann、Novomesky、Racanska、Svec

  DOI：——

  日期：——