(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride | 1123889-54-2

• 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: (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride
• 英文别名: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-pyrrolidin-2-yl]methyl]thiourea;hydrochloride
• CAS: 1123889-54-2
• 化学式: C₁₄H₁₅F₆N₃S*ClH
• 分子量: 407.811
• InChiKey: QWTAAJVXPHMAPH-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride 、 氯化烟碱盐酸盐 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-1-(pyridine-3-carbonyl)pyrrolidin-2-yl]methyl]thiourea
  参考文献：
  名称：

  Synthesis of Chiral NADH Analog Based on Proline Template Including Thiourea and Nicotinic Acid Moieties

  摘要：

  Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed.

  DOI：

  10.1080/00397911.2010.505702
• 作为产物：
  描述：

  (S)-2-(甲苯磺酰氧基甲基)吡咯烷-1-甲酸叔丁酯 在 甲醇 、 sodium azide 、 palladium on carbon 、 氢气 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride
  参考文献：
  名称：

  Synthesis of Chiral NADH Analog Based on Proline Template Including Thiourea and Nicotinic Acid Moieties

  摘要：

  Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed.

  DOI：

  10.1080/00397911.2010.505702
• 作为试剂：
  描述：

  4-戊烯醛 、 tert-butyl 4-[(4-methoxybenzyl)oxy]-2-oxobutanoate 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 Tert-butyl 3-formyl-2-hydroxy-2-[2-[(4-methoxyphenyl)methoxy]ethyl]hex-5-enoate
  参考文献：
  名称：

  Asymmetric synthesis of (+)-trachyspic acid

  摘要：

  Aldol reaction of di-tert-butyl 4-(4-methoxybenzyloxy)-2-oxobutanoate with pent-4-enal using (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride as a catalyst, followed by Pinnick oxidation and tert-butyl esterification, gave (2S,3S)-di-tert-butyl 2-(2-(4-methoxybenzyloxy)ethyl)-3-allyl-2-hydroxysuccinate in high optical purity (85% ee), from which the total synthesis of (+)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.004

文献信息

• Synthesis of Chiral NADH Analog Based on Proline Template Including Thiourea and Nicotinic Acid Moieties
  作者：Gintautas Bagdžiūnas、Matti Haukka、Eugenijus Butkus

  DOI：10.1080/00397911.2010.505702

  日期：2011.9.1

  Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed.