1-chloro-3-((4-methoxyphenyl)amino)propan-2-ol | 3470-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-chloro-3-((4-methoxyphenyl)amino)propan-2-ol
• 英文别名: 1-Chloro-3-(4-methoxyanilino)-2-propanol；1-chloro-3-(4-methoxyanilino)propan-2-ol
• CAS: 3470-93-7
• 化学式: C₁₀H₁₄ClNO₂
• 分子量: 215.68
• InChiKey: ZJOZYSYLTJRYMS-UHFFFAOYSA-N

物化性质

• 沸点：
  391.0±37.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-3-((4-methoxyphenyl)amino)propan-2-ol 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 1-(3,6-dibromo-9H-carbazol-9-yl)-3-((4-methoxyphenyl)amino)propan-2-ol
  参考文献：
  名称：

  Aminopropyl carbazole analogues as potent enhancers of neurogenesis

  摘要：

  Neural stem cells are multipotent and self-renewing cells that can differentiate into new neurons and hold great promise for treating various neurological disorders including multiple sclerosis, Parkinson's disease, and Alzheimer's disease. Small molecules that can trigger neurogenesis and neuroprotection are particularly useful not only because of their therapeutic implications but also because they can provide an invaluable tool to study the mechanisms of neurogenesis. In this report, we have developed and screened 25 aminopropyl carbazole derivatives that can enhance neurogenesis of cultured neural stem cells. Among these analogues, compound 9 demonstrated an excellent proneurogenic and neuroprotective activity with no apparent toxicity. We believe that compound 9 can serve as an excellent lead to develop various analogues and to study the underlying mechanisms of neurogenesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.066
• 作为产物：
  描述：

  甲氧苯胺 、 环氧氯丙烷 在 lithium bromide 作用下， 生成 1-chloro-3-((4-methoxyphenyl)amino)propan-2-ol
  参考文献：
  名称：

  1-氨基-3-氯丙-2-醇衍生物和二硫化碳碱介导合成环状二硫代氨基甲酸酯

  摘要：

  描述了一种有效制备六元环二硫代氨基甲酸酯的方法，其中三乙胺有效促进1-氨基-3-氯丙-2-醇衍生物与二硫化碳的反应。在实验和理论研究的基础上，提出了一种反应机制来解释本反应与我们之前报道的二氧化碳固定之间的差异。

  DOI：

  10.1039/d3ob01070h

文献信息

• Catalytic metallodendrimers grafted on mesoporous polymethacrylate beads for the regioselective synthesis of β-amino alcohols under solvent-free conditions
  作者：Richa Tiwari、Sachdeo H. Daware、Sandeep B. Kale

  DOI：10.1039/c5ra04903b

  日期：——

  Metallodendrimer-grafted mesoporous polymethyacrylate beads for the regioselective, solvent-free, efficient and scalable catalytic synthesis of β-amino alcohols at ambient temperature.

  金属树枝状大分子接枝的中孔聚甲基丙烯酸甲酯珠，用于在室温下区域选择性、无溶剂、高效且可扩展的催化合成β-氨基醇。
• Efficient solvent-free aminolysis of epoxides under (C4H12N2)2[BiCl6]Cl·H2O catalysis
  作者：Hong-Fei Lu、Lei-Lei Sun、Wen-Jun Le、Fei-Fei Yang、Jun-Tao Zhou、Yu-Hua Gao

  DOI：10.1016/j.tetlet.2012.05.079

  日期：2012.8

  An efficient and rapid procedure for ring opening of various epoxides with aromatic, aliphatic and heterocyclic amines is developed at room temperature under solvent-free conditions in the presence of (C4H12N2)2[BiCl6]Cl·H2O (1 mol %). This catalyst can be reused several times without losing of its activity.

  在（C 4 H 12 N 2）2 [BiCl 6 ] Cl·H 2 O存在下，在室温下在无溶剂的条件下，开发了一种高效快速的方法，可用于芳族，脂族和杂环胺的各种环氧化物的开环。（1摩尔％）。该催化剂可以重复使用几次而不会失去其活性。
• Highly Regioselective and Efficient Synthesis of Aminoepoxides by Ring Closure of Aminohalohydrins Mediated by KF-Celite
  作者：Vittorio Pace、Pilar Hoyos、José Sinisterra、Andrés Alcántara、Wolfgang Holzer

  DOI：10.1055/s-0030-1260961

  日期：2011.8

  The regioselective synthesis of several aminoepoxides has beenachieved without observing any trace of azetidinols, which are usuallyreported as the exclusive reaction products when aminohalohydrinsare treated with bases. The use of the mild supported base KF-Celitein refluxing acetonitrile is crucial for modulating the excellentregioselectivity observed.

  几种氨基环氧化物的区域选择性合成已经在没有观察到任何痕量氮杂环丁烷醇的情况下实现，当氨基卤代醇用碱处理时，氮杂环丁醇通常被报道为唯一的反应产物。使用温和支持的碱 KF-Celitein 回流乙腈对于调节观察到的优异区域选择性至关重要。
• Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral <i>N</i>-Aryl Epoxy Amines and CO₂
  作者：Yuseop Lee、Jonghoon Choi、Hyunwoo Kim

  DOI：10.1021/acs.orglett.8b02186

  日期：2018.8.17

  achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A

  N-芳基环氧胺与CO 2之间发生了发散性偶联反应。通过使用两种不同的助催化剂，碘化四丁基铵碘化物（TBAI）或4-二甲基氨基吡啶（DMAP）以及Al（III）Lewis酸，分别通过两种不同的反应途径选择性地生产环状碳酸酯或恶唑烷酮。所提出的反应机理得到产物的立体化学测定的支持。成功实现了克利奈唑胺的克级生产。
• Switchable synthesis of cyclic carbamates by carbon dioxide fixation at atmospheric pressure
  作者：Yasunori Toda、Minoru Shishido、Tatsuya Aoki、Kimiya Sukegawa、Hiroyuki Suga

  DOI：10.1039/d1cc02493k

  日期：——

  base-promoted switchable synthesis of five- and six-membered cyclic carbamates using atmospheric pressure carbon dioxide as the C1 source was developed. The chemoselectivity of products was simply controlled by changing bases and solvents. The reaction proceeds effectively under mild conditions, affording valuable cyclic carbamates. Experimental results and DFT studies revealed the reaction mechanism.

  开发了使用大气压二氧化碳作为 C1 源的五元和六元环状氨基甲酸酯的碱基促进可切换合成。产品的化学选择性可以通过改变碱和溶剂来简单地控制。该反应在温和条件下有效进行，得到有价值的环状氨基甲酸酯。实验结果和 DFT 研究揭示了反应机理。