N-tert-butyl-4-methoxycarbonylbenzylamine

• 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: N-tert-butyl-4-methoxycarbonylbenzylamine
• 英文别名: Methyl 4-[(tert-butylamino)methyl]benzoate
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD09733839
• 分子量: 221.299
• InChiKey: AGOCJWCBUFHCIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-4-methoxycarbonylbenzylamine 在 过氧化双月桂酰 、 三氟甲磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.75h， 生成 3-氧代-2,3-二氢-1H-异吲哚-5-羧酸甲酯
  参考文献：
  名称：

  Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products

  摘要：

  An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.003
• 作为产物：
  描述：

  methyl-4-((tert-butylimino)methyl)benzoate 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 反应 0.5h， 以98%的产率得到N-tert-butyl-4-methoxycarbonylbenzylamine
  参考文献：
  名称：

  在无溶剂条件下用固体酸活化的硼氢化钠对醛和酮进行直接和间接还原胺化

  摘要：

  描述了一种简单方便的程序，用于在无溶剂条件下，使用硼酸，对甲苯磺酸一水合物或苯甲酸作为还原剂活化的硼氢化钠还原性胺化醛和酮。

  DOI：

  10.1016/j.tet.2005.04.039

文献信息

• Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions
  作者：Byung Tae Cho、Sang Kyu Kang

  DOI：10.1016/j.tet.2005.04.039

  日期：2005.6

  A simple and convenient procedure for reductive amination of aldehydes and ketones using sodium borohydride activated by boric acid, p-toluenesulfonic acid monohydrate or benzoic acid as reducing agent under solvent-free conditions is described.

  描述了一种简单方便的程序，用于在无溶剂条件下，使用硼酸，对甲苯磺酸一水合物或苯甲酸作为还原剂活化的硼氢化钠还原性胺化醛和酮。
• Clean and Simple Chemoselective Reduction of Imines to Amines Using Boric Acid-Activated Sodium Borohydride under Solvent-Free Conditions
  作者：Byung Tae Cho、Sang Kyu Kang

  DOI：10.1055/s-2004-829066

  日期：——

  The first clean and highly effective solvent-free chemoselective reduction of functionalized aldimines and ketimines bearing easily reducible functional groups, such as ke- tone, carboxylic acid, ester, nitrile, amide, nitro, furyl and alkenyl groups, to the corresponding amines using boric acid-activated sodium borohydride is described.

  首次使用硼酸将带有易还原官能团（例如酮、羧酸、酯、腈、酰胺、硝基、呋喃基和烯基）的官能化醛亚胺和酮亚胺进行清洁且高效的无溶剂化学选择性还原，生成相应的胺描述了酸活化的硼氢化钠。
• Carbamoyl radicals from carbamoylxanthates: a facile entry into isoindolin-1-ones
  作者：Germán López-Valdez、Simón Olguín-Uribe、Luis D. Miranda

  DOI：10.1016/j.tetlet.2007.09.142

  日期：2007.11

  It has been found that carbamoylxanthates derived from secondary t-butyl amines are stable compounds which function as efiicient sources of carbamoyl radicals. The carbamoylxanthates derived from t-butylbenzylamines can be efficiently transformed into 2- t-butylisoindolin-1-ones via an oxidative radical cyclization process. The carbamoylxanthates derived from N-t-butylamino olefins underwent the expected cyclization/xanthate-transfer process to afford the corresponding pyrrolidones and piperidones under thermally induced DLP fragmentation conditions and in the presence of catalytic Et3B in air, at room temperature. (C) 2007 Elsevier Ltd. All rights reserved.
• NOVEL CYCLOSPORIN DERIVATIVES AND USES THEREOF
  申请人：S&T Global Inc.

  公开号：US20190151403A1

  公开（公告）日：2019-05-23

  A compound of the Formula (I) is disclosed: (I) or pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification. Also described are a pharmaceutical composition comprising the same and a method for treating or preventing viral infections, inflammation, dry eye, central nervous disorders, cardiovascular diseases, cancer, obesity, diabetes, muscular dystrophy, lung, and liver, and kindey diseases, and hair loss using the same.
• Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products
  作者：Germán López-Valdez、Simón Olguín-Uribe、Alejandra Millan-Ortíz、Rocio Gamez-Montaño、Luis D. Miranda

  DOI：10.1016/j.tet.2011.01.003

  日期：2011.4

  An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. (C) 2011 Elsevier Ltd. All rights reserved.