(R,R)-N,N'-bis(1-cyclohexylethyl)thiourea | 158072-26-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫脲类
• 英文名称: (R,R)-N,N'-bis(1-cyclohexylethyl)thiourea
• 英文别名: 1,3-bis[(1R)-1-cyclohexylethyl]thiourea
• CAS: 158072-26-5
• 化学式: C₁₇H₃₂N₂S
• 分子量: 296.52
• InChiKey: OOBXWULCSMGIBU-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R,R)-N,N'-bis(1-cyclohexylethyl)thiourea 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.83h， 生成 (N,N′-(R)-(-)-1-cyclohexylethylcarbamimidoyl)dicyclohexylphosphine borane
  参考文献：
  名称：

  Synthesis of Phosphaguanidines by Hydrophosphination of Carbodiimides with Phosphine Boranes

  摘要：

  The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes, under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.

  DOI：

  10.1021/jo501841s
• 作为产物：
  描述：

  二硫化碳 、 (R)-(-)-1-环己基乙胺 以96%的产率得到(R,R)-N,N'-bis(1-cyclohexylethyl)thiourea
  参考文献：
  名称：

  通过“混合”试剂无溶剂合成手性 N,N'-二取代硫脲

  摘要：

  报道了通过使用环保的无溶剂和微波辅助方法合成新的手性硫脲 3a-f，并且出乎意料的是，在前一种方法中，只需混合起始材料即可立即获得产物。还报道了 3b、3c 和 3e 的晶体结构。

  DOI：

  10.1055/s-2004-829167

文献信息

• Thioureas and their cyclized derivatives: Synthesis, conformational analysis and antimicrobial evaluation
  作者：Senel Teke Tuncel、Sule Erol Gunal、Melike Ekizoglu、Nesrin Gokhan Kelekci、Safiye S. Erdem、Ece Bulak、Wolfgang Frey、Ilknur Dogan

  DOI：10.1016/j.molstruc.2018.10.055

  日期：2019.3

  conformation. The thiazolidin-4-ones have been found to be present only in the anti-conformation. All compounds were screened for antimicrobial activity against 4 bacteria. For three of the compounds with the highest antimicrobial activity, the antimicrobial evaluation was expanded using more reference strains and clinical isolates. Among the compounds studied the 5-benzylidene-thiazolidine-4-ones 15RR, 15SS

  摘要 几种单一的对映异构体硫脲已被合成并转化为它们的环状衍生物：2-imino-thiazolidin-4-ones。硫脲的构象已在溶液和固态中测定。在溶液中；已经观察到 E,Z 和 Z,E 构象之间的相互转换，ΔG≠ 值约为 50 kJ/mol，而在固态下它们显示具有 Z,Z 构象。已发现 thiazolidin-4-ones 仅存在于反构象中。筛选所有化合物对 4 种细菌的抗微生物活性。对于具有最高抗菌活性的三种化合物，使用更多参考菌株和临床分离株扩大了抗菌评估。在研究的化合物中，5-苯亚甲基-噻唑烷-4-酮 15RR，15SS 和带有苄基吡咯烷支架的硫脲 5RR 显示出比其他更好的抗菌活性。发现所有化合物的杀真菌活性均优于杀菌活性。
• Enantiomerically pure guanidine-catalysed asymmetric nitroaldol reaction
  作者：Rafael Chinchilla、Carmen Nájera、Pablo Sánchez-Agulló

  DOI：10.1016/0957-4166(94)80183-5

  日期：1994.7

  Enantiomerically pure guanidines with and without C-2 symmetry have been prepared and used as catalysts in the addition of nitromethane to aldehydes (Henry reaction). The influence of the structure and amount of the guanidine, the solvent and the temperature in the enantioselectivity of the nitroaldol reaction has also been studied.
• Synthesis of Phosphaguanidines by Hydrophosphination of Carbodiimides with Phosphine Boranes
  作者：Carl A. Busacca、John A. Milligan、Eakkaphon Rattanangkool、Cyrus Ramavarapu、Anji Chen、Anjan K. Saha、Zhibin Li、Heewon Lee、Steven J. Geib、Guijun Wang、Chris H. Senanayake、Peter Wipf

  DOI：10.1021/jo501841s

  日期：2014.10.17

  The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes, under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.
• Solvent-Free Synthesis of Chiral <i>N</i>,<i>N</i>′-Disubstituted Thioureas by ‘Just Mixing’ the Reagents
  作者：René Gutiérrez、Jaime Vázquez、Sylvain Bernès、Yasmi Reyes、Mónica Moya、Pankaj Sharma、Cecilio Alvarez

  DOI：10.1055/s-2004-829167

  日期：——

  The synthesis of new chiral thioureas 3a-f by using the ecofriendly solvent-free and microwave-assisted approaches is reported and, unexpectedly, in the former method by just mixing the starting materials the products areinstantaneously obtained. The crystal structures for 3b, 3c and 3e are also reported.

  报道了通过使用环保的无溶剂和微波辅助方法合成新的手性硫脲 3a-f，并且出乎意料的是，在前一种方法中，只需混合起始材料即可立即获得产物。还报道了 3b、3c 和 3e 的晶体结构。