(1,2,3,4-tetrahydronaphthalen-1-yl)carbamic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1,2,3,4-tetrahydronaphthalen-1-yl)carbamic acid methyl ester
• 英文别名: methyl (1,2,3,4-tetrahydronaphthalen-1-yl)carbamate；methyl N-(1,2,3,4-tetrahydronaphthalen-1-yl)carbamate
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: BBIAGNCSRBJKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-phenylbutyryl)carbamic acid methyl ester 在 四氯化钛 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 (1,2,3,4-tetrahydronaphthalen-1-yl)carbamic acid methyl 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

• Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations
  作者：Qilei Zhu、Emily C. Gentry、Robert R. Knowles

  DOI：10.1002/anie.201604619

  日期：2016.8.16

  weak C−O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO. as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic

  描述了一种新的催化方法，该方法通过烷氧基胺自由基阳离子的介观裂解来获得碳正离子中间体。在此过程中，激发态氧化剂与TEMPO衍生的烷氧基胺底物之间的电子转移会产生带有非常弱的C-O键的自由基阳离子。自发断裂导致形成稳定的硝基自由基TEMPO 。以及可被多种亲核试剂截获的反应性碳正离子中间体。值得注意的是，该过程在中性条件下和相对温和的电势下发生，从而在酸敏感和易氧化的亲核分子同时存在的情况下能够产生催化阳离子。
• MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20140051724A1

  公开（公告）日：2014-02-20

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜导电调节因子，其组成物和使用这些调节剂的方法。本发明还涉及使用这种调节剂治疗ABC转运蛋白介导的疾病的方法。
• 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.
• US8741925B2
  申请人：——

  公开号：US8741925B2

  公开（公告）日：2014-06-03
• 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.