1-(4-chlorophenyl)-N-(3,4-dimethoxyphenyl)methanimine | 326611-65-8

• 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: 1-(4-chlorophenyl)-N-(3,4-dimethoxyphenyl)methanimine
• CAS: 326611-65-8
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: OLQHZQDAMWVPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-N-(3,4-dimethoxyphenyl)methanimine 在 sodium tetrahydroborate 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 乙醚 为溶剂， 反应 21.0h， 生成 (2S,3S)-3-(4-chlorophenyl)-3-(3,4-dimethoxyanilino)-2-methylpropan-1-ol
  参考文献：
  名称：

  使用有机催化方法与L-脯氨酸合成旋光的1,2,3-三取代的氮杂环丁烷

  摘要：

  报道了一种针对光学活性的1,2,3-三取代氮杂环丁烷的简洁的有机催化方法，包括对合成序列范围和限制的研究。该合成包括取代的苯甲醛，苯胺和可烯化的醛之间的一锅l-脯氨酸促进的三组分反应，然后将所得的β-氨基醛原位还原为相应的γ-氨基醇，最后通过后者的分子内环化作用原位形成中间体甲苯磺酸盐的方法。

  DOI：

  10.1016/j.tetlet.2013.01.090
• 作为产物：
  描述：

  4-氯苯甲醛 、 3,4-二甲氧基苯胺 以 甲醇 为溶剂， 生成 1-(4-chlorophenyl)-N-(3,4-dimethoxyphenyl)methanimine
  参考文献：
  名称：

  环丙烷甲醛和N-苄基苯胺的无金属开环环化：对功能化苯并[b]氮杂衍生物的生态友好利用

  摘要：

  在此，我们报道了对丙烷磺酸和环丙烷苯甲醛与N-苄基苯胺的对甲苯磺酸（PTSA）引发的温和且用户友好的开环/多米诺环开环反应（取决于N-苄基苯胺中存在的取代基） 4-氨基丁醛/ 2,3-二氢-1 H-苯并[ b ]氮杂。产物二氢-1 H-苯并[ b ]氮杂也被转化为相应的四氢-1 H-苯并[ b ]氮杂。

  DOI：

  10.1002/adsc.201801714

文献信息

• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• An Efficient Method for the Synthesis of Indolo[3,2-<i>c</i>]quinoline Derivatives Catalyzed by Iodine
  作者：Yujing Zhou、Meimei Zhang、Mingyue Yin、Xiangshan Wang

  DOI：10.1002/cjoc.201200993

  日期：2013.2

  The reaction of Schiff base and indole catalyzed by iodine in DMA, subsequently treated with DDQ, gave indolo[3,2‐c]quinoline derivatives in good yields. The structure of 3e was confirmed by X‐ray diffraction analysis.

  碘在DMA中催化席夫碱和吲哚的反应，随后用DDQ处理，得到的吲哚[3,2- c ]喹啉衍生物收率很高。X射线衍射分析证实了3e的结构。
• Asymmetric Construction of Nitrogen-Containing [2.2.2] Bicyclic Scaffolds Using <i>N</i>-(<i>p</i>-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide
  作者：Hua Yang、Rich G. Carter

  DOI：10.1021/jo9009062

  日期：2009.8.7

  An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.
• Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with l-proline
  作者：Marcela Amongero、Teodoro S. Kaufman

  DOI：10.1016/j.tetlet.2013.01.090

  日期：2013.4

  A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot l-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting β-aminoaldehydes to

  报道了一种针对光学活性的1,2,3-三取代氮杂环丁烷的简洁的有机催化方法，包括对合成序列范围和限制的研究。该合成包括取代的苯甲醛，苯胺和可烯化的醛之间的一锅l-脯氨酸促进的三组分反应，然后将所得的β-氨基醛原位还原为相应的γ-氨基醇，最后通过后者的分子内环化作用原位形成中间体甲苯磺酸盐的方法。
• Metal‐Free Ring Opening Cyclization of Cyclopropane Carbaldehydes and <i>N</i> ‐Benzyl Anilines: An Eco‐Friendly Access to Functionalized Benzo[ <i>b</i> ]azepine Derivatives
  作者：Raghunath Dey、Prabal Banerjee

  DOI：10.1002/adsc.201801714

  日期：2019.6.18

  Herein, we report a p‐toluenesulfonic acid (PTSA) initiated mild and user‐friendly ring opening/domino ring opening cyclization reaction (depends on substituent present in N‐benzyl aniline) of cyclopropane carbaldehyde and N‐benzyl aniline towards the formation of substituted 4‐amino butanal/2,3‐dihydro‐1H‐benzo[b]azepine. The product dihydro‐1H‐benzo[b]azepine was also converted into the corresponding

  在此，我们报道了对丙烷磺酸和环丙烷苯甲醛与N-苄基苯胺的对甲苯磺酸（PTSA）引发的温和且用户友好的开环/多米诺环开环反应（取决于N-苄基苯胺中存在的取代基） 4-氨基丁醛/ 2,3-二氢-1 H-苯并[ b ]氮杂。产物二氢-1 H-苯并[ b ]氮杂也被转化为相应的四氢-1 H-苯并[ b ]氮杂。