N-benzyl-[C-²H₃]acetamide | 114533-13-0

• 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-benzyl-[C-²H₃]acetamide
• 英文别名: N-benzyl-2,2,2-trideuterioacetamide
• CAS: 114533-13-0
• 化学式: C₉H₁₁NO
• 分子量: 152.169
• InChiKey: UZJLYRRDVFWSGA-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-苯基三氟甲磺酸甲胺 在 sodium hydroxide 、 水 、 dinitrogen tetraoxide 、 sodium carbonate 作用下， 以 氘代乙腈 为溶剂， 生成 N-benzyl-[C-²H₃]acetamide
  参考文献：
  名称：

  Alkyl diazonium ion pairs and deamination. Part 45. The preparation of carbonium ions and other high-energy alkylating agents under mild conditions

  摘要：

  DOI：

  10.1021/ja00219a082

文献信息

• Expedient synthesis of deuterium-labelled amides within micro-reactors
  作者：Julian Hooper、Paul Watts

  DOI：10.1002/jlcr.1254

  日期：2007.3.15

  The pharmaceutical industry relies heavily on the synthesis of small quantities (10–500 mg) of stable, isotopically labelled compounds in the evaluation of new drug candidates for metabolism studies. As a result of the phenomenal cost of labelled materials even the preparation of small quantities can be extremely expensive. In this paper, for the first time, we report that micro-reactor technology may be used to prepare stable deuterium-labelled compounds by conducting all optimization experiments using unlabelled precursors and simply substituting the labelled derivatives once the optimization is complete. Here, we wish to present a simple, general procedure for the synthesis of amides containing isotopic labels demonstrated using [C-2H3]acetyl chloride 1. The reaction is carried out within a micro-reactor set-up which we believe offers superiority over other reported methods viz requiring stoichiometric quantities of reagents, high containment of the system and generality of the technique, obtaining products in high yields. Copyright © 2007 John Wiley & Sons, Ltd.

  制药行业在评估新药候选物的代谢研究中，严重依赖于合成稳定的同位素标记化合物的小批量（10-500毫克）。由于标记材料的成本非常高，即使是准备小批量也可能极其昂贵。 在本文中，我们首次报告微反应器技术可以用来制备稳定的氘标记化合物，通过使用未标记前体进行所有优化实验，一旦优化完成，只需替换标记衍生物即可。在这里，我们希望呈现一个简单通用的合成含有同位素标签的酰胺的程序，使用[C-2H3]乙酰氯1作为示例。反应在微反应器系统中进行，我们认为该系统在其它已报道的方法中具有优势，例如需要重量比的试剂、高度封闭的系统和技术的通用性，从而获得高产率的产品。版权所有 © 2007 John Wiley & Sons, Ltd.
• Transamidation of primary amides with amines catalyzed by zirconocene dichloride
  作者：Benjamin N. Atkinson、A. Rosie Chhatwal、Helen V. Lomax、James W. Walton、Jonathan M. J. Williams

  DOI：10.1039/c2cc37427g

  日期：——

  Zirconocene dichloride (Cp(2)ZrCl(2)) has been shown to be an effective catalyst for the transamidation of primary amides with amines in cyclohexane at 80 degrees C in 5-24 hours. For favourable substrates, the reaction can be performed at temperatures as low as 30 degrees C.

  二氯化锆（Cp（2）ZrCl（2））已显示是在环己烷中于80摄氏度下于5-24小时内将伯酰胺与胺进行氨基转移的有效催化剂。对于有利的底物，反应可以在低至30摄氏度的温度下进行。
• Photosensitized Oxidation of Alkyl Phenyl Sulfoxides. C−S Bond Cleavage in Alkyl Phenyl Sulfoxide Radical Cations
  作者：Enrico Baciocchi、Tiziana Del Giacco、Osvaldo Lanzalunga、Paolo Mencarelli、Barbara Procacci

  DOI：10.1021/jo801088n

  日期：2008.8.1

  deriving from the heterolytic C−S bond cleavage in the sulfoxide radical cations (alcohols, R1R2R3COH, and acetamides, R1R2R3CNHCOCH3) accompanied by sulfur-containing products (phenyl benzenethiosulfinate, diphenyl disulfide, and phenyl benzenethiosulfonate). By laser irradiation, the formation of 3-CN-NMQ• (λmax = 390 nm) and sulfoxide radical cations 1•+, 2•+, and 5•+ (λmax = 550 nm) was observed within

  的3-氰基Ñ -methylquinolinium高氯酸盐（3-CN-NMQ + CLO 4 - ）苯基烷基亚砜的-photosensitized氧化（PhSOCR 1 - [R 2 - [R 3，1，R 1 = R 2 = H，R 3 = Ph值; 2，R 1＝ H，R 2＝ Me，R 3＝ Ph；3，R 1＝ R 2＝ Ph，R 3＝ H；4，R 1＝ R 2＝ Me，R 3＝ Ph；5，R 1 = R 2 = R 3 = Me）已通过稳态辐射和MeCN中氮下的纳秒激光闪光光解（LFP）进行了研究。稳态光解表明，亚砜自由基阳离子（醇，R 1 R 2 R 3 COH和乙酰胺，R 1 R 2 R 3 CNHCOCH 3）中杂合C-S键的裂解产生了产物，并伴随着硫-含有产品（苯苯硫基磺酸盐，二苯二硫和苯苯硫基磺酸盐）。通过激光辐照，形成3-CN-NMQ •（λmax= 390 nm）和亚砜自由基阳离子1
• WHITE, EMIL H.;DEPINTO, JEFFREY T.;POLITO, ALBERT J.;BAUER, INES;ROSWELL,+, J. AMER. CHEM. SOC., 110,(1988) N 11, 3708-3709
  作者：WHITE, EMIL H.、DEPINTO, JEFFREY T.、POLITO, ALBERT J.、BAUER, INES、ROSWELL,+

  DOI：——

  日期：——
• Alkyl diazonium ion pairs and deamination. Part 45. The preparation of carbonium ions and other high-energy alkylating agents under mild conditions
  作者：Emil H. White、Jeffrey T. DePinto、Albert J. Polito、Ines. Bauer、David F. Roswell

  DOI：10.1021/ja00219a082

  日期：1988.5