1-(2-甲氧基苯基)吡咯烷 | 4787-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-甲氧基苯基)吡咯烷
• 英文名称: 1-(2-methoxyphenyl)pyrrolidine
• 英文别名: N-(2-methoxyphenyl)pyrrolidine
• CAS: 4787-76-2
• 化学式: C₁₁H₁₅NO
• mdl: MFCD20486332
• 分子量: 177.246
• InChiKey: CXJDHKPUONWJBP-UHFFFAOYSA-N

物化性质

• 沸点：
  139 °C(Press: 10 Torr)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧基苯基)吡咯烷 在 叔丁基过氧化氢 、 sodium acetate 作用下， 以 环己烷 为溶剂， 反应 24.0h， 以64%的产率得到8-methoxy-1-(2-methoxyphenyl)-2,3,3a,3b,4,5,6,11b-octahydro-1H-dipyrrolo[1,2-a:3′,2′-c]quinoline
  参考文献：
  名称：

  N-芳基吡咯烷与T-HYDRO反应生成的烯胺和亚胺离子中间体的环加成反应

  摘要：

  在 NaOAc·3H2O 存在下，N-芳基吡咯烷衍生物与 70% 的叔丁基氢过氧化物 (T-HYDRO) 的反应通过相应的亚胺离子和烯胺中间体的环加成反应得到四环胺，产率为 59-78%。环己烷溶剂。亚胺离子中间体与甲醇中的 t-BuOK 反应以 85-88% 的产率得到相应的环酰胺，或者使用 t-BuOK 和硝基甲烷的甲醇进行烷基化以 74-79% 的产率得到相应的硝基甲基产物。

  DOI：

  10.1055/s-0035-1560185
• 作为产物：
  描述：

  四氢吡咯 、 邻苯二甲醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以70%的产率得到1-(2-甲氧基苯基)吡咯烷
  参考文献：
  名称：

  Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction

  摘要：

  Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic amination reaction are described.

  DOI：

  10.1021/jo00071a019

文献信息

• Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of <i>N</i>-Aryl Pyrrolidines
  作者：Hanbyeol Jo、Ahmed H. E. Hassan、Seung Young Jung、Jae Kyun Lee、Yong Seo Cho、Sun-Joon Min

  DOI：10.1021/acs.orglett.8b00098

  日期：2018.2.16

  A concise synthesis of 8-azabicyclo[3.2.1]octanes via sequential oxidative Mannich reactions is described. This approach involves an intermolecular oxidative Mannich coupling reaction between N-aryl pyrrolidines with TMS enol ether and a subsequent intramolecular oxidative Mannich cyclization of the corresponding silyl enol ether. DDQ is used as a key oxidant for both reactions.

  描述了通过顺序氧化曼尼希反应的简明合成8-氮杂双环[3.2.1]辛烷的方法。该方法涉及N-芳基吡咯烷与TMS烯醇醚之间的分子间氧化曼尼希偶联反应和随后的相应的甲硅烷基烯醇醚的分子内氧化曼尼希环化。DDQ用作两个反应的关键氧化剂。
• Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
  作者：Yuanguang Chen、Fangyu Du、Fengyang Chen、Qifan Zhou、Guoliang Chen

  DOI：10.1055/s-0039-1690702

  日期：2019.12

  selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and

  在胺或唑与芳基卤的选择性N-芳基化反应中，发现甲基-α - d-吡喃葡萄糖苷（MG）作为铜粉的绿色配体起作用。另外，氮杂环胺化合物还可与杂环芳基氯进行N-芳基化偶联。该方法允许在温和的反应条件下获得各种芳族胺和芳基唑，具有良好的耐受性，并且以中等至高收率进行。
• 트로페인(Tropane) 알칼로이드 화합물 및 순차적 산화반응을 이용한 이의 제조방법
  申请人：Industry-University Cooperation Foundation Hanyang University ERICA Campus 한양대학교 에리카산학협력단(120120008551) Corp. No ▼ 131471-0017977BRN ▼134-82-10205

  公开号：KR20200033606A

  公开（公告）日：2020-03-30

  본 발명은 산화적 만니히(Mannich) 고리반응을 순차적으로 이용하는 트로페인 알칼로이드 화합물 및 이의 제조방법에 관한 것이다. 본 발명은 하기의 화학식 1구조를 가지는 트로페인 알칼로이드 화합물을 제공한다. [화학식 1] (R은 H, o-OMe p-OMe, o,p-OMe, p-t-Bu, p-F 또는 p-Cl 이며, R는 H 또는 CHOCH)

  本发明涉及利用氧化曼尼奇（Mannich）环反应的顺序使用，涉及的是特罗芬醛化合物及其制造方法。本发明提供具有以下化学式1结构的特罗芬醛化合物。[化学式1]（R是H，o-OMe p-OMe，o,p-OMe，p-t-Bu，p-F或p-Cl，R是H或CHOCH）。
• Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime
  作者：Chunling Yuan、Lei Zhang、Yingdai Zhao

  DOI：10.3390/molecules24224177

  日期：——

  We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaffolds found in FDA-approved pharmaceuticals.

  我们首次报道了一种新的应用于改进铜催化的C-N偶联反应的金属螯合配体α-苯甲醛肟。该体系能够催化(hetero)芳基卤代物与各种亲核试剂（例如唑类化合物、哌啶、吡咯啉和氨基酸）的偶联反应，产率从中等到优良不等。该方案可快速获得FDA批准的药物中常见的骨架。
• <i>N</i>-(1-Oxy-2-picolyl)oxalamic Acid as an Efficient Ligand for Copper-Catalyzed Amination of Aryl Iodides at Room Temperature
  作者：Yongbin Wang、Jing Ling、Yu Zhang、Ao Zhang、Qizheng Yao

  DOI：10.1002/ejoc.201500279

  日期：2015.7

  N-(1-Oxy-pyridin-2-ylmethyl)oxalamic acid was identified as efficient ligand for CuI-catalyzed amination of aryl halides at room temperature. In our catalytic system, N-arylation of cyclic secondary amines, primary amines, amino acids, and ammonia proceeded with moderate to excellent yields and high functional group tolerance.

  N-(1-Oxy-pyridin-2-ylmethyl) 草氨酸被确定为室温下 CuI 催化的芳基卤化物胺化的有效配体。在我们的催化系统中，环状仲胺、伯胺、氨基酸和氨的 N-芳基化以中等至优异的产率和高官能团耐受性进行。