chroman-4-yl-carbamic acid benzyl ester

• 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: chroman-4-yl-carbamic acid benzyl ester
• 英文别名: benzyl chroman-4-ylcarbamate；benzyl N-(3,4-dihydro-2H-chromen-4-yl)carbamate
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: CCYAOWBKLTVZNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3-phenoxy-propionyl)-carbamic acid benzyl ester 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.67h， 生成 chroman-4-yl-carbamic acid benzyl ester
  参考文献：
  名称：

  The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic N-Acylimines:  Application to the Synthesis of (±)-Sertraline

  摘要：

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.

  DOI：

  10.1021/jo010370l

文献信息

• Novel synthetic method for allylic amination of cyclic allylic ethers using chlorosulfonyl isocyanate
  作者：Sang Hwi Lee、In Su Kim、Qing Ri Li、Guang Ri Dong、Young Hoon Jung

  DOI：10.1016/j.tetlet.2011.02.036

  日期：2011.4

  The introduction of amines to allylic or benzylic position of cyclic compounds with chlorosulfonyl isocyanate is developed in high to excellent yields. This method provides a novel access to biologically active compounds including the framework of 1-aminoindanes, 1-aminotetralines, and 1-amino-2-hydroxy cyclic compounds. Mechanistic evidence for the reaction pathway is also provided.

  以高至优异的产率开发了将胺引入环状化合物的烯丙基或苄基位置与氯磺酰基异氰酸酯的方法。该方法提供了一种新的生物活性化合物的途径，包括1-氨基茚满，1-氨基四氢呋喃和1-氨基-2-羟基环状化合物。还提供了反应途径的机理证据。
• Efficient generation and intramolecular cyclization reactions of acyl imines
  作者：Michael P. DeNinno、Cynthia Eller

  DOI：10.1016/s0040-4039(97)01531-1

  日期：1997.9

  Acyl carbamates can be selectively reduced with diisobutyl aluminum hydride to provide high yields of N-acyl hemiaminals 1. With appropriate substitution, these intermediates undergo Lewis acid catalyzed intramolecular exo cyclization reactions to afford l-amino 1,2,3,4-tetrahydronaphthalene derivatives. (C) 1997 Elsevier Science Ltd.
• DÉRIVÉS DE 5-BENZYLISOQUINOLÉINE POUR LE TRAITEMENT DE MALADIES CARDIOVASCULAIRES
  申请人：Les Laboratoires Servier

  公开号：EP3107900B1

  公开（公告）日：2017-11-15
• The Preparation and Intra- and Intermolecular Addition Reactions of Acyclic <i>N</i>-Acylimines:  Application to the Synthesis of (±)-Sertraline
  作者：Michael P. DeNinno、Cynthia Eller、John B. Etienne

  DOI：10.1021/jo010370l

  日期：2001.10.1

  Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.