(R,R)-N,N'-bis(1-phenylethyl)thiourea | 67375-00-2

• 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: (R,R)-N,N'-bis(1-phenylethyl)thiourea
• 英文别名: Bis[(S)-(-)-alpha-Methylbenzyl]thiourea；1,3-bis[(1R)-1-phenylethyl]thiourea
• CAS: 67375-00-2
• 化学式: C₁₇H₂₀N₂S
• 分子量: 284.425
• InChiKey: OCIUEYSMBBAERM-ZIAGYGMSSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  409.4±48.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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-phenylethyl)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)-(+)-methylbenzylcarbamimidoyl)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(+)-alpha-甲基苄胺 以97%的产率得到(R,R)-N,N'-bis(1-phenylethyl)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

• A Convenient Method for the Preparation of Primary and Symmetrical N,N′-Disubstituted Thioureas
  作者：R. Jason Herr、J. Louise Kuhler、Harold Meckler、Chester J. Opalka

  DOI：10.1055/s-2000-7607

  日期：——

  A convenient process for the preparation of both primary thioureas 2 and symmetrical N,N′-disubstituted thioureas 6 based on the condensation of amine hydrohalides 5 with potassium thiocyanate has been developed. This approach tolerates sterically bulky primary amine substrates (both chiral and achiral), and the products can usually be isolated by a simple filtration of the reaction mixture. This method is an especially attractive alternative for the synthesis of thioureas when the corresponding isothiocyanates are unavailable, or difficult to prepare. It is also worth noting that a wide variety of amine hydrohalides, which are used in this procedure, are commercially available.

  本研究开发了一种便捷的合成方法，通过胺的氢卤酸盐5与硫氰酸钾的缩合反应，可以制备初级硫脲2和对称的N,N'-二取代硫脲6。这种方法适用于空间位阻大的初级胺底物（包括手性和非手性），并且通常通过简单的反应混合物过滤即可分离产物。当相应的异硫氰酸酯无法获得或难以制备时，这种方法是合成硫脲的特别有吸引力的替代方案。值得注意的是，在该方法中使用的多种胺的氢卤酸盐在商业上是可获得的。
• 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。
• A Comparison of Topical and Retrobulbar Anesthesia for Trabeculectomy
  作者：Norman A. Zabriskie、Iqbal Ike K. Ahmed、Alan S. Crandall、Brad Daines、Thomas A. Burns、Bhupendra C. K. Patel

  DOI：10.1097/00061198-200208000-00006

  日期：2002.8

  Purpose  To compare the safety and efficacy of topical versus retrobulbar anesthesia for primary trabeculectomy Methods  A prospective study of 36 consecutive patients undergoing trabeculectomy who were randomized to receive topical (n = 18) or retrobulbar (n = 18) anesthesia. Operating conditions, patient comfort, and surgical outcome were evaluated. Settings  Tertiary-care university hospital ambulatory surgical center. Results  There were no differences in operating conditions (P = 0.14), pain during (P = 0.54) or after (P = 0.76) surgery, or supplemental anesthesia required (P = 0.34) between the two groups. Very few patients in either group were bothered by touch sensation, tissue manipulation, or the microscope light. Chemosis, subconjunctival hemorrhage and eyelid hemorrhage were seen exclusively in the retrobulbar group (P <0.03), and were all attributable to the injection. Inadvertent eye movement was present more frequently in the topical group (P = 0.01), although this did not pose a problem to the surgeon. No surgical complications were encountered in either group. Conclusion  Topical anesthesia is a safe and effective alternative to retrobulbar anesthesia for primary trabeculectomy.

  目的 比较初级小梁切除术中局部麻醉与球后麻醉的安全性和有效性 方法 对连续接受小梁切除术的 36 名患者进行前瞻性研究，随机分配患者接受局部麻醉（18 人）或球后麻醉（18 人）。对手术条件、患者舒适度和手术结果进行了评估。 地点 大学附属医院门诊手术中心。 结果 两组患者在手术条件（P = 0.14）、术中疼痛（P = 0.54）或术后疼痛（P = 0.76）以及所需的辅助麻醉（P = 0.34）方面均无差异。两组患者中只有极少数人对触觉、组织操作或显微镜光线感到不适。化脓、结膜下出血和眼睑出血仅见于球后组患者（P <0.03），且均可归因于注射。局部注射组出现眼球意外移动的频率更高（P = 0.01），不过这并没有给外科医生造成困扰。两组患者均未出现手术并发症。 结论 局部麻醉是初级小梁切除术中球后麻醉的一种安全有效的替代方法。
• Synthesis of Symmetrical <i>N,N</i><i>‘</i>-Disubstituted Thioureas and Heterocyclic Thiones from Amines and CS₂ over a ZnO/Al₂O₃ Composite as Heterogeneous and Reusable Catalyst
  作者：Marco Ballabeni、Roberto Ballini、Franca Bigi、Raimondo Maggi、Mauro Parrini、Giovanni Predieri、Giovanni Sartori

  DOI：10.1021/jo981629b

  日期：1999.2.1
• MCM-41-TBD as a new, efficient, supported heterogeneous catalyst for the synthesis of thioureas
  作者：Roberto Ballini、Giovanna Bosica、Dennis Fiorini、Raimondo Maggi、Paolo Righi、Giovanni Sartori、Raffaella Sartorio

  DOI：10.1016/s0040-4039(02)02100-7

  日期：2002.11

  The preparation of thioureas, by reaction of carbon disulfide with primary amines, can be efficiently catalyzed, under heterogeneous conditions, by MCM-TBD as a new and reusable catalyst. (C) 2002 Elsevier Science Ltd. All rights reserved.