N,N′-bis(tert-butoxycarbonyl)-N′′-tert-butylguanidine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N′-bis(tert-butoxycarbonyl)-N′′-tert-butylguanidine
• 英文别名: N,N'-bis(tert-butoxycarbonyl)-N''-tert-butylguanidine；N,N'-bis(tert-butoxycarbonyl)-N"-tert-butylguanidine；tert-butyl N-[N'-tert-butyl-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• 化学式: C₁₅H₂₉N₃O₄
• 分子量: 315.413
• InChiKey: WTQOAGHYEYZMMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二(叔丁氧基羰基)胍 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N,N′-bis(tert-butoxycarbonyl)-N′′-tert-butylguanidine
  参考文献：
  名称：

  Diprotected Triflylguanidines:  A New Class of Guanidinylation Reagents

  摘要：

  DOI：

  10.1021/jo980425s

文献信息

• Efficient synthetic protocol for substituted guanidines via copper(I)-mediated intermolecular amination of isothiourea derivatives
  作者：Hitoshi Ube、Daisuke Uraguchi、Masahiro Terada

  DOI：10.1016/j.jorganchem.2006.06.046

  日期：2007.1

  Amination of S-methyl-N,N′-bis-Boc-isothiourea with either primary or sterically hindered secondary amines promoted by copper(I) chloride and K2CO3 gave N,N′-bis-Boc protected guanidines in good to excellent yields under mild reaction conditions.

  用氯化铜（I）和K 2 CO 3促进的伯或空间位阻仲胺对S-甲基-N，N'-双-Boc-异硫脲进行胺化，得到N，N'-双-Boc保护的胍在温和的反应条件下具有优异的收率。
• Reagents for Efficient Conversion of Amines to Protected Guanidines
  作者：Jan Izdebski、Tomasz Gers、Danuta Kunce、Paweł Markowski

  DOI：10.1055/s-2003-44374

  日期：——

  Two new guanidinylation reagents, N,N′-bis(ortho-chloro-Cbz)-S-methylisothiourea and N,N′-bis(ortho-bromo-Cbz)-S-methylisothiourea, were compared with the already known N,N′-bis(Boc)-S-methylisothiourea and N,N′-bis(Cbz)-S-methylisothiourea. The new reagents proved to be superior to the known reagents. The reactions with all the new reagents were accelerated by addition of DMAP. N,N′-Bis(ortho-chloro-Cbz)- and N,N′-bis(ortho-bromo-Cbz)guanidines are stable when treated with trifluoroacetic acid and can be converted to guanidines by hydrogenolysis.

  两种新的胍化试剂，N,N′-双(邻氯-Cbz)-S-甲基异硫脲和N,N′-双(邻溴-Cbz)-S-甲基异硫脲，与已知的N,N′-双(Boc)-S-甲基异硫脲和N,N′-双(Cbz)-S-甲基异硫脲进行了比较。结果表明，新试剂优于已知试剂。与所有新试剂的反应在添加DMAP后被加速。N,N′-双(邻氯-Cbz)和N,N′-双(邻溴-Cbz)胍在用三氟醋酸处理时稳定，并且可以通过氢解转化为胍。
• 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。
• A Convenient Preparation of Monosubstituted<i>N</i>,<i>N</i>′-di(Boc)-Protected Guanidines
  作者：Brian Drake、Marcel Patek、Michal Lebl

  DOI：10.1055/s-1994-25527

  日期：——

  1-H-Pyrazole-1-[N,N′-bis(tert-butoxycarbonyl)] carboxamidine (1) reacts under mild conditions with a number of amines and amino acids to give the respective protected guanidines in moderate to high isolated yields.

  1-H 吡唑-1-[N,N′-双（叔丁氧羰基）]羧酰胺（1）在温和的条件下与多种胺和氨基酸反应，生成相应的受保护胍类化合物，分离产率从中等到高等不等。