((3R,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester

• 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: ((3R,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester
• 英文别名: Tert-butyl [(3R,4S)-1-benzyl-4-(trifluoromethyl)-3-pyrrolidinyl]methylcarbamate；tert-butyl N-[[(3R,4S)-1-benzyl-4-(trifluoromethyl)pyrrolidin-3-yl]methyl]carbamate
• 化学式: C₁₈H₂₅F₃N₂O₂
• 分子量: 358.404
• InChiKey: CYXDSWPWFYUGPO-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3R,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到((3R,4R)-4-Trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of 2-pyridones: II. 8-(Fluoro-substituted pyrrolidinyl)-2-pyridones as antibacterial agents

  摘要：

  The 8-position side chain of 2-pyridones is believed to be involved in the binding with bacterial DNA gyrase to form the ternary complex, making them very important for the activity of 2-pyridones. A series of 2-pyridones having fluoro-substituted amines at the 8-position has been synthesized and their antibacterial activities and pharmacokinetic properties are reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00355-2
• 作为产物：
  描述：

  ethyl (+/-)-(3R,4R)-1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate 在 lithium aluminium tetrahydride 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 生成 ((3R,4S)-1-Benzyl-4-trifluoromethyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of 2-pyridones: II. 8-(Fluoro-substituted pyrrolidinyl)-2-pyridones as antibacterial agents

  摘要：

  The 8-position side chain of 2-pyridones is believed to be involved in the binding with bacterial DNA gyrase to form the ternary complex, making them very important for the activity of 2-pyridones. A series of 2-pyridones having fluoro-substituted amines at the 8-position has been synthesized and their antibacterial activities and pharmacokinetic properties are reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00355-2

文献信息

• Synthesis and antibacterial activity of novel 7-(3-substituted-3 or 4-trifluoromethyl-1-pyrrolidinyl)-8-methoxyfluoroquinolones
  作者：Hideto Fukui、Tetsuo Shibata、Takanobu Naito、Jun Nakano、Tetsuro Maejima、Hisato Senda、Wakao Iwatani、Yoshiyuki Tatsumi、Masahiro Suda、Ta-i Arika

  DOI：10.1016/s0960-894x(98)00514-9

  日期：1998.10

  The titled compounds were synthesized and evaluated for in vitro antibacterial activity. The (3R,4S)-3-aminomethyl-4-trifluoromethyl derivative (S-34109) was confirmed to be optimal because of its superior activity against quinolone and methicillin-resistant Staphyrococcus aureus and low side effect potential. (C) 1998 Elsevier Science Ltd. All rights reserved.