(S)-9H-fluorenylmethyl 2-(phenylcarbamoyl)pyrrolidine-1-carboxylate | 403478-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-9H-fluorenylmethyl 2-(phenylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: 9H-fluoren-9-ylmethyl (2S)-2-(phenylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 403478-34-2
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: ADJXZSWVPFHFLJ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-9H-fluorenylmethyl 2-(phenylcarbamoyl)pyrrolidine-1-carboxylate 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-n-苯基-2-吡咯烷羧酰胺
  参考文献：
  名称：

  Discovery and structure–activity relationships of urea derivatives as potent and novel CCR3 antagonists

  摘要：

  The synthesis and structure-activity relationships of ureas as CCR3 antagonists are described. Optimization starting with lead compound 2 (IC50 = 190 nM) derived from initial screening hit compound 1 (IC50 = 600 nM) led to the identification of (S)-N-((1R,3S,5S)-8-((6-fluoronaphthalen-2-yl)methyl)-8-azabicyclo[3.2.1]octan-3-yl)-N-(2-nitrophenyl)pyrrolidine-1,2-dicarboxamide 27 (IC50 = 4.9 nM) as a potent CCR3 antagonist. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.042
• 作为产物：
  描述：

  Fmoc-L-脯氨酸 、 苯胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到(S)-9H-fluorenylmethyl 2-(phenylcarbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

  摘要：

  A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-L-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.035

文献信息

• A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant
  作者：Takuya Kanemitsu、Atsushi Umehara、Rieko Haneji、Kazuhiro Nagata、Takashi Itoh

  DOI：10.1016/j.tet.2012.03.035

  日期：2012.5

  A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-L-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). (C) 2012 Elsevier Ltd. All rights reserved.
• Discovery and structure–activity relationships of urea derivatives as potent and novel CCR3 antagonists
  作者：Aiko Nitta、Yosuke Iura、Hiroki Tomioka、Ippei Sato、Koichiro Morihira、Hirokazu Kubota、Tatsuaki Morokata、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto、Takayuki Imaoka、Toshiya Takahashi

  DOI：10.1016/j.bmcl.2012.06.042

  日期：2012.8

  The synthesis and structure-activity relationships of ureas as CCR3 antagonists are described. Optimization starting with lead compound 2 (IC50 = 190 nM) derived from initial screening hit compound 1 (IC50 = 600 nM) led to the identification of (S)-N-((1R,3S,5S)-8-((6-fluoronaphthalen-2-yl)methyl)-8-azabicyclo[3.2.1]octan-3-yl)-N-(2-nitrophenyl)pyrrolidine-1,2-dicarboxamide 27 (IC50 = 4.9 nM) as a potent CCR3 antagonist. (c) 2012 Elsevier Ltd. All rights reserved.