4-methoxy-N-(oxiran-2-ylmethyl)aniline | 1198800-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-N-(oxiran-2-ylmethyl)aniline
• 英文别名: (4-methoxyphenyl)(oxiranylmethyl)amine
• CAS: 1198800-42-8
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: APMPOPFSBFAQQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(oxiran-2-ylmethyl)aniline 、 二苯甲基哌嗪 在 aluminium(III) triflate 、 碳酸氢钠 作用下， 以 甲苯 、 水 为溶剂， 反应 5.0h， 以81%的产率得到1-(4-benzhydrylpiperazin-1-yl)-3-(4-methoxyphenylamino)propan-2-ol
  参考文献：
  名称：

  Al(OTf)₃-Mediated Epoxide Ring-Opening Reactions: Toward Piperazine-Derived Physiologically Active Products

  摘要：

  Al(OTf)(3) is a good catalyst for the ring opening of epoxides, forming beta-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molecule or the other, allowing insight into a best-case approach for the ring-opening step. Each half of the molecule contained an heteroatom that could be used either to attach the glycidyl moiety or as the nucleophile in the ring-opening reaction, for the same set of reagents, allowing this approach.

  DOI：

  10.1021/jo9020437
• 作为产物：
  描述：

  1-chloro-3-((4-methoxyphenyl)amino)propan-2-ol 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-methoxy-N-(oxiran-2-ylmethyl)aniline
  参考文献：
  名称：

  手性N-芳基环氧胺和CO 2的立体控制，发散性，Al（III）催化偶联

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.8b02186

文献信息

• 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。
• Aminopropyl carbazole analogues as potent enhancers of neurogenesis
  作者：Hye Jin Yoon、Sun-Young Kong、Min-Hye Park、Yongsung Cho、Sung-Eun Kim、Jae-Yeon Shin、Sunghye Jung、Jiyoun Lee、Farhanullah、Hyun-Jung Kim、Jeewoo Lee

  DOI：10.1016/j.bmc.2013.08.066

  日期：2013.11

  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.
• Al(OTf)₃-Mediated Epoxide Ring-Opening Reactions: Toward Piperazine-Derived Physiologically Active Products
  作者：D. Bradley G. Williams、Adam Cullen

  DOI：10.1021/jo9020437

  日期：2009.12.18

  Al(OTf)(3) is a good catalyst for the ring opening of epoxides, forming beta-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molecule or the other, allowing insight into a best-case approach for the ring-opening step. Each half of the molecule contained an heteroatom that could be used either to attach the glycidyl moiety or as the nucleophile in the ring-opening reaction, for the same set of reagents, allowing this approach.
• Continuous organocatalytic flow synthesis of 2-substituted oxazolidinones using carbon dioxide
  作者：Nicola Zanda、Leijie Zhou、Esther Alza、Arjan W. Kleij、Miquel À. Pericàs

  DOI：10.1039/d2gc00503d

  日期：——

  organocatalytic continuous flow approach to promote the efficient synthesis of a small library of pharmaceutically relevant 2-substituted oxazolidinones, including the known drug Toloxatone. A packed bed reactor containing the same batch of immobilized catalyst could be applied for the continuous synthesis of a series of heterocyclic products over a two week period without significant changes in catalytic activity

  聚苯乙烯负载的 1,5,7-triazabicyclodec-5-ene (TBD) 被用作高度可回收且稳定的催化剂，用于将环氧胺转化为各种 2-恶唑烷酮支架。该方法将使用 CO 2作为有吸引力、廉价且丰富的 C 1源与无卤有机催化连续流动方法相结合，以促进有效合成药学相关的 2-取代恶唑烷酮小型库，包括已知的药物 Toloxatone . 包含同一批固定化催化剂的填充床反应器可用于在两周内连续合成一系列杂环产品，而催化活性不会发生显着变化。