1-[4-chloro-3-trifluoromethylphenyl]-2,3-di(tert-butoxycarbonyl)guanidine | 1443231-54-6

• 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: 1-[4-chloro-3-trifluoromethylphenyl]-2,3-di(tert-butoxycarbonyl)guanidine
• 英文别名: N,N′-bis(tert-butoxycarbonyl)-N′′-4-chloro-3-(trifluoromethyl)guanidine；N,N'-bis(tert-butoxycarbonyl)-N''-(4-chloro-3-(trifluoromethyl)guanidine)；tert-butyl N-[N'-[4-chloro-3-(trifluoromethyl)phenyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1443231-54-6
• 化学式: C₁₈H₂₃ClF₃N₃O₄
• 分子量: 437.847
• InChiKey: RODCMCWQRLSPAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 、 三乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 16.5h， 生成 1-[4-chloro-3-trifluoromethylphenyl]-2,3-di(tert-butoxycarbonyl)guanidine
  参考文献：
  名称：

  Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N′-disubstituted guanidines

  摘要：

  We present a concise, less-toxic and broadly applicable method for coupling weakly nucleophilic amines with N,N'-di-(tert-butoxycarbonyl)thiourea, N-(tert-butxoycarbonyl), N'-alkyl/arylsubstituted-thioureas and N,N'-di-(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of copper(II) chloride. Subsequent removal of Boc protecting groups affords guanidines, di-substituted guanidines and 2-aminoimidazolines in modest to excellent overall yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.070

文献信息

• Synthesis of guanidines via the I2 mediated desulfurization of N,N′-di-Boc-thiourea
  作者：Hao-Jie Rong、Cui-Feng Yang、Tao Chen、Yong-Qiang Wang、Bin-Ke Ning

  DOI：10.1016/j.tetlet.2019.150970

  日期：2019.8

  The I2 mediated desulfurization of N,N′-di-Boc-thiourea was developed. Various primary amines, including sterically and electronically deactivated primary amines, were transformed into the corresponding bis-Boc protected guanidines under mild conditions.

  开发了I 2介导的N， N'-di-Boc-硫脲的脱硫。在温和条件下，将各种伯胺，包括空间和电子失活的伯胺，转化为相应的双-Boc保护的胍。
• Iodine-catalyzed guanylation of amines with<i>N</i>,<i>N</i>′-di-Boc-thiourea
  作者：Hao-Jie Rong、Cui-Feng Yang、Tao Chen、Ze-Gang Xu、Tian-Duo Su、Yong-Qiang Wang、Bin-Ke Ning

  DOI：10.1039/c9ob02014d

  日期：——

  Herein, we report that iodine-catalyzed guanylation of primary amines can be accomplished with N,N'-di-Boc-thiourea and TBHP to afford the corresponding guanidines in 40-99% yields. Oxidation of the HI byproduct by TBHP eliminates the need for an extra base to prevent the protonation of substrates and makes the reaction especially useful for both electronically and sterically deactivated primary anilines

  本文中，我们报道了碘催化的伯胺的鸟嘌呤化可以用N，N'-di-Boc-硫脲和TBHP来完成，从而以40-99％的产率提供相应的胍。TBHP对HI副产物的氧化消除了对防止底物质子化的额外碱的需要，并使该反应特别适用于电子和空间失活的初级苯胺。