ethyl 1-{N-[(S)-1-phenylethyl]aminoacetyl}cyclopropanecarboxylate | 412295-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 1-{N-[(S)-1-phenylethyl]aminoacetyl}cyclopropanecarboxylate
• 英文别名: ethyl 1-[2-[N-[1-(S)-phenylethyl]amino]acetyl]cyclopropanecarboxylate；ethyl 1-[2-[[(1S)-1-phenylethyl]amino]acetyl]cyclopropane-1-carboxylate
• CAS: 412295-15-9
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: JIYWDYWUAOBCPJ-LBPRGKRZSA-N

物化性质

• 沸点：
  371.9±32.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-{N-[(S)-1-phenylethyl]aminoacetyl}cyclopropanecarboxylate 在 4 Angstroem MS 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.0h， 生成 ethyl 1-{4-fluoro-2,5-dihydro-5-oxo-1-[(S)-1-phenylethyl]-1H-pyrrol-3-yl}cyclopropanecarboxylate
  参考文献：
  名称：

  Practical Synthesis of DQ-113, a New Quinolone Antibacterial Agent, by Using the Intramolecular Horner-Wadsworth- Emmons Reaction

  摘要：

  A practical route was developed for synthesizing the C-7 substituent of DQ-113 (6, 5-amino-7-[(3S,4R)-4-(1-aminocycloprop-l-yl)-3-fluoro-pyrrolidin-l-yl]-6-fluoro-l-[(IR,2S)-2-fluorocyclopropan-l-yl]-1,4-dihydro- 8-methyl-4-oxoquinolin-3-carboxylic acid), a new quinolone antibacterial agent for serious infections caused by Gram-positive pathogens. The key step was the intramolecular Homer-Wadsworth-Emmons reaction. In addition, the yield of the final aromatic micleophilic substitution reaction was improved.

  DOI：

  10.3987/com-03-9972
• 作为产物：
  描述：

  1-乙酰基环丙烷羧酸乙酯 在 溴 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 ethyl 1-{N-[(S)-1-phenylethyl]aminoacetyl}cyclopropanecarboxylate
  参考文献：
  名称：

  DEHALOGENO COMPOUNDS

  摘要：

  公开号：

  EP1336611B1

文献信息

• Dehalogeno compounds
  申请人：——

  公开号：US20040063754A1

  公开（公告）日：2004-04-01

  3-(1-Aminocycloalkyl)pyrrolidinyl-substituted-6-dehalodeno(hydrogen-substituted)quinolon carboxylic acid derivatives having specific substitunets as represented by the following formula (I), its salts, and hydrates thereof exhibit a broad and potent antibacterial activity on gram-negative and gram-positive bacteria, in particular, resistant bacteria typified by gram-positive cocci, including MRSA, PRSP and VRE. Thus these compounds are usable as drugs. 1

  具有特定取代基的3-(1-氨基环烷基)吡咯烷基取代的6-去卤代(氢取代)喹诺酮羧酸衍生物及其盐和水合物，如下式(I)所示，表现出广谱和强效的抗菌活性，对革兰氏阴性菌和革兰氏阳性菌均有效，特别是对革兰氏阳性球菌等耐药菌，包括MRSA、PRSP和VRE有良好的抗菌活性。因此这些化合物可用作药物。
• Dehalogeno-compounds
  申请人：Takahashi Hisashi

  公开号：US20070123560A1

  公开（公告）日：2007-05-31

  3-(1-Aminocycloalkyl)pyrrolidinyl-substituted-6-dehalodeno(hydrogen-substituted)quinolon carboxylic acid derivatives having specific substituents as represented by the following formula (I), its salts, and hydrates thereof exhibit a broad and potent antibacterial activity on gram-negative and gram-positive bacteria, in particular, resistant bacteria typified by gram-positive cocci, including MRSA, PRSP and VRE. Thus these compounds are usable as drugs.

  具有特定取代基的3-(1-氨基环烷基)吡咯烷基取代的6-去卤代（氢取代）喹诺酮羧酸衍生物，其盐和水合物，如以下公式（I）所示，表现出广谱和强效的抗菌活性，对革兰氏阴性和革兰氏阳性细菌均有效，特别是对革兰氏阳性球菌等耐药菌，包括MRSA、PRSP和VRE。因此，这些化合物可用作药物。
• DEHALOGENO COMPOUNDS
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1336611B1

  公开（公告）日：2007-09-05
• Design, synthesis and biological evaluations of novel 7-[3-(1-aminocycloalkyl)pyrrolidin-1-yl]-6-desfluoro-8-methoxyquinolones with potent antibacterial activity against multi-drug resistant Gram-positive bacteria
  作者：Rie Miyauchi、Katsuhiro Kawakami、Masao Ito、Norikazu Matsuhashi、Hitoshi Ohki、Hiroaki Inagaki、Hisashi Takahashi、Makoto Takemura

  DOI：10.1016/j.bmc.2009.08.026

  日期：2009.10

  A series of novel 6-desfluoro [des-F(6)] and 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methoxyquinolones bearing 3-(1-aminocycloalkyl)pyrrolidin-1-yl substituents at the C-7 position (1-6) was synthesized to obtain potent drugs for nosocomial infections caused by Gram-positive pathogens. The des-F(6) compounds 4-6 exhibited at least four times more potent activity against representative Gram-positive bacteria than ciprofloxacin or moxifloxacin. Among the derivatives, 7-[(3R)-3-(1-aminocyclopropan-1-yl)pyrrolidin-1-yl] derivative 4, which showed favorable profiles in preliminary toxicological and non-clinical pharmacokinetic studies, exhibited potent antibacterial activity against clinically isolated Gram-positive pathogens that had become resistant to one or more antibiotics. (C) 2009 Elsevier Ltd. All rights reserved.
• US7902226B2
  申请人：——

  公开号：US7902226B2

  公开（公告）日：2011-03-08