1-benzyl-1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-pyrrolidin-2-yl]methyl]urea | 1262193-06-5

• 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: 1-benzyl-1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-pyrrolidin-2-yl]methyl]urea
• CAS: 1262193-06-5
• 化学式: C₂₁H₂₁F₆N₃O
• 分子量: 445.408
• InChiKey: BHBGQWSVRCODSQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  S-叔丁氧羰基-2-(氨基乙基)吡咯烷 在 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 4.0h， 生成 1-benzyl-1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-pyrrolidin-2-yl]methyl]urea
  参考文献：
  名称：

  Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

  摘要：

  A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.038
• 作为试剂：
  描述：

  反式硝基苯乙烯 、 异丁醛 在 1-benzyl-1-[3,5-bis(trifluoromethyl)phenyl]-3-[[(2S)-pyrrolidin-2-yl]methyl]urea 作用下， 反应 216.25h， 生成 (R)-2,2-dimethyl-4-nitro-3-phenylbutanal 、 (3S)-2,2-dimethyl-4-nitro-3-phenylbutanal
  参考文献：
  名称：

  Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

  摘要：

  A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.038

文献信息

• Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect
  作者：Xiao-Yu Cao、Jun-Cheng Zheng、Yu-Xue Li、Zhen-Cao Shu、Xiu-Li Sun、Bi-Qin Wang、Yong Tang

  DOI：10.1016/j.tet.2010.10.038

  日期：2010.12

  A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.