benzyl (S)-2-((3-(3,5-bis(trifluoromethyl)phenyl)thioureido)methyl)pyrrolidine-1-carboxylate | 1321848-92-3

• 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: benzyl (S)-2-((3-(3,5-bis(trifluoromethyl)phenyl)thioureido)methyl)pyrrolidine-1-carboxylate
• 英文别名: (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(N-carbobenzyloxypyrrolidin-2-ylmethyl)thiourea；benzyl (2S)-2-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 1321848-92-3
• 化学式: C₂₂H₂₁F₆N₃O₂S
• 分子量: 505.484
• InChiKey: LRLPMMQGUUHBMI-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双[(三氟代甲基)磺酰基]甲烷 、 benzyl (S)-2-((3-(3,5-bis(trifluoromethyl)phenyl)thioureido)methyl)pyrrolidine-1-carboxylate 在 mercury(II) oxide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 1,4-二氧六环 为溶剂， 反应 25.0h， 以51%的产率得到(S)-N-(3,5-bis(trifluoromethyl)phenyl)-N'-(pyrrolidin-2-ylmethyl)-2,2-bis((trifluoromethyl)sulfonyl)ethene-1,1-diamine
  参考文献：
  名称：

  新型氢键供体有机催化剂的设计及其在不对称直接羟醛反应中的应用

  摘要：

  针对环己酮与芳香醛的直接醇醛缩合反应，检测了具有不同pKa 值的双氢键供体单元的各种有机催化剂的不对称催化活性。具有最高酸性基序的有机催化剂产生具有最高对映选择性的相应羟醛产物。直接羟醛反应的不对称催化活性与双氢键供体单元的酸度之间观察到良好的相关性。

  DOI：

  10.1055/s-0036-1558971
• 作为产物：
  描述：

  (2S)-2-(4-methylphenylsulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester 在 sodium azide 、 水 、 氯化铵 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 benzyl (S)-2-((3-(3,5-bis(trifluoromethyl)phenyl)thioureido)methyl)pyrrolidine-1-carboxylate
  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：

  2-[(4-甲氧基苯基)亚氨基]-1,2-二苯基乙酮 在 二氢吡啶 、 benzyl (S)-2-((3-(3,5-bis(trifluoromethyl)phenyl)thioureido)methyl)pyrrolidine-1-carboxylate 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 2-[(4-甲氧基苯基)氨基]-1,2-二苯基-乙酮
  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

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.
• Design of Novel Hydrogen-Bonding Donor Organocatalysts and Their Application to Asymmetric Direct Aldol Reaction
  作者：Tsuyoshi Miura、Hiroshi Akutsu、Kosuke Nakashima、Hikaru Yanai、Akira Kotani、Shin-ichi Hirashima、Tomoyuki Yamamoto、Ryuta Takahashi、Akihiro Yoshida、Yuji Koseki、Hideki Hakamata、Takashi Matsumoto

  DOI：10.1055/s-0036-1558971

  日期：2017.7

  showing different pK a values were examined for direct aldol reactions of cyclohexanone with aromatic aldehydes. Organocatalyst with motif exhibiting the highest acidity resulted in the corresponding aldol products with the highest enantioselectivity. A good correlation has been observed between the asymmetric catalytic activity for direct aldol reactions and acidities of double hydrogen-bonding donating

  针对环己酮与芳香醛的直接醇醛缩合反应，检测了具有不同pKa 值的双氢键供体单元的各种有机催化剂的不对称催化活性。具有最高酸性基序的有机催化剂产生具有最高对映选择性的相应羟醛产物。直接羟醛反应的不对称催化活性与双氢键供体单元的酸度之间观察到良好的相关性。