(4-phenylbutyryl)carbamic acid methyl ester | 197173-13-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4-phenylbutyryl)carbamic acid methyl ester
• 英文别名: methyl 4-phenylbutanoylcarbamate；methyl N-(4-phenylbutanoyl)carbamate
• CAS: 197173-13-0
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: ZMSXTVJAQHZGCP-UHFFFAOYSA-N

物化性质

• 熔点：
  121.5-122 °C
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  9-(3-phenylpropyl)-9-borabicyclo[3.3.1]nonane 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 、 4-甲基苯磺酸吡啶 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 (4-phenylbutyryl)carbamic acid methyl ester
  参考文献：
  名称：

  通过有机硼与N- [甲氧基（甲硫基）亚甲基]氨基甲酸甲酯的钯催化的单碳延伸反应偶联制备酰亚胺

  摘要：

  描述了通过钯催化的偶联反应作为一碳延伸反应制备酰亚胺。在噻吩-2-羧酸铜（I）存在下，芳基-，烷基-和烯基硼与N- [甲氧基（甲硫基甲基）亚甲基]氨基甲酸酯的钯催化偶联反应提供亚氨基醚，该亚氨基醚被转化为酸水解得到相应的酰亚胺，产率很高。亚氨基醚也可用于制备相应的酯而不使用一氧化碳。

  DOI：

  10.1021/ol303062a

文献信息

• Correction to Preparation of Imides via the Palladium-Catalyzed Coupling Reaction of Organoborons with Methyl <i>N</i>-[Methoxy(methylthio)methylene]carbamate as a One-Carbon Elongation Reaction
  作者：Takuhei Tomizawa、Kohei Orimoto、Takashi Niwa、Masahisa Nakada

  DOI：10.1021/ol500435y

  日期：2014.3.7

  the spectrum was reprocessed and has been replaced for compound 6b in the revised Supporting Information submitted with this correction. Compounds 8a and 8c–e were resynthesized, and the new spectra are provided in the revised Supporting Information submitted with this correction. The spectra editing did not affect any of the conclusions of the published paper. The yields were found to be correct. Revised

  在支持信息中，发现化合物6b，8a和8c – e的1 H NMR光谱已被编辑以除去溶剂和杂质。找到了化合物6b的原始FID ，并对光谱进行了重新处理，并已在通过此更正提交的修订后的《支持信息》中替换了化合物6b。化合物8a和8c – e进行了重新合成，并在与此更正一起提交的修订后的《支持信息》中提供了新光谱。光谱编辑不会影响已发表论文的任何结论。发现产率是正确的。修订后的文件包括化合物6b，8a和8c – e的再处理光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。这篇文章被1个出版物引用。修订后的文件包括化合物6b，8a和8c – e的再处理光谱。可通过Internet（http://pubs.acs.org）免费获得此材料。
• 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.