tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,4,7,7a-hexahydro-3aH-isoindole-3a-carboxylate | 1037368-24-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,4,7,7a-hexahydro-3aH-isoindole-3a-carboxylate
• 英文别名: [(1S,6R)-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid tert-butyl ester；tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]-3,4,7,7a-tetrahydroisoindole-3a-carboxylate
• CAS: 1037368-24-3
• 化学式: C₂₁H₂₇NO₃
• 分子量: 341.45
• InChiKey: GZOXLNVEGKXEIS-LDBYXDLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,4,7,7a-hexahydro-3aH-isoindole-3a-carboxylate 在 红铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 38.5h， 生成 tert-butyl {(3aS,7aS)-2-[(1R)-1-phenylethyl]-1,2,3,4,7,7a-hexahydro-3aH-isoindol-3a-yl}carbamate
  参考文献：
  名称：

  在 C-7 位带有稠合吡咯烷基部分的新型 8-甲氧基喹诺酮类药物的设计、合成和生物学评价，对呼吸道病原体具有有效的抗菌活性

  摘要：

  Novel 8-methoxyquinolones bearing fused pyrrolidinyl moieties at the C-7 position were designed, synthesized, and evaluated for their potent antibacterial activity for the treatment of respiratory tract infections. Compound 5, possessing a trans-fused octahydroisoindole ring at the C-7 position of the quinolone scaffold, exhibited potent in vitro antibacterial activity against nosocomial respiratory pathogens including levofloxacin-resistant Escherichia coli and methicillin-resistant Staphylococcus aureus strains. Furthermore, compound 5 showed a favorable pharmacokinetic profile after a single oral administration in rats.

  DOI：

  10.3987/com-18-13889
• 作为产物：
  描述：

  tert-butyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]-3-(prop-2-en-1-yl)pyrrolidine-3-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 tert-butyl (3aS,7aR)-1-oxo-2-[(1R)-1-phenylethyl]-1,2,3,4,7,7a-hexahydro-3aH-isoindole-3a-carboxylate
  参考文献：
  名称：

  在 C-7 位带有稠合吡咯烷基部分的新型 8-甲氧基喹诺酮类药物的设计、合成和生物学评价，对呼吸道病原体具有有效的抗菌活性

  摘要：

  Novel 8-methoxyquinolones bearing fused pyrrolidinyl moieties at the C-7 position were designed, synthesized, and evaluated for their potent antibacterial activity for the treatment of respiratory tract infections. Compound 5, possessing a trans-fused octahydroisoindole ring at the C-7 position of the quinolone scaffold, exhibited potent in vitro antibacterial activity against nosocomial respiratory pathogens including levofloxacin-resistant Escherichia coli and methicillin-resistant Staphylococcus aureus strains. Furthermore, compound 5 showed a favorable pharmacokinetic profile after a single oral administration in rats.

  DOI：

  10.3987/com-18-13889

文献信息

• Fused substituted aminopyrrolidine derivative
  申请人：Takahashi Hisashi

  公开号：US20120108582A1

  公开（公告）日：2012-05-03

  A quinolone synthetic antibacterial agent having excellent properties as a medicine is provided, which has strong antibacterial activity not only to Gram-negative bacteria but also to Gram-positive cocci that have low sensitivity to quinolone antibacterial agents, and which exhibits high safety and excellent pharmacokinetics. A compound represented by the formula (I) or a salt thereof, or a hydrate thereof. Specifically, a quinolone derivative of the formula (I) wherein substituents R6 and R7 taken together with the carbon atoms to which they are bonded form a cyclic structure which may contain an oxygen atom as a ring constituent atom, the cyclic structure forming a 5-4, 5-5, or 5-6 fused bicyclic pyrrolidinyl substituent, the substituent being bonded to a quinolone mother skeleton Q containing a pyridobenzoxazine structure.

  提供了一种具有极好药物特性的喹诺酮合成抗菌剂，其不仅对革兰氏阴性菌具有强烈的抗菌活性，而且对对喹诺酮抗菌剂敏感度较低的革兰氏阳性球菌也具有强烈的抗菌活性，并表现出高安全性和优异的药代动力学特性。该化合物由式(I)或其盐或水合物表示，具体而言，是式(I)的喹诺酮衍生物，其中取代基R6和R7与它们所连接的碳原子一起形成一个环状结构，该环状结构可能包含一个氧原子作为环状成分原子，该环状结构形成一个5-4、5-5或5-6融合的双环吡咯烷基取代物，该取代物与含有吡啶苯并噁嗪结构的喹诺酮母骨架Q连接。
• Fused Substituted Aminopyrrolidine Derivative
  申请人：Daiichi Sankyo Company, Limited

  公开号：US20140142096A1

  公开（公告）日：2014-05-22

  A quinolone synthetic antibacterial agent having excellent properties as a medicine is provided, which has strong antibacterial activity not only to Gram-negative bacteria but also to Gram-positive cocci that have low sensitivity to quinolone antibacterial agents, and which exhibits high safety and excellent pharmacokinetics. A compound represented by the formula (I) or a salt thereof, or a hydrate thereof. Specifically, a quinolone derivative of the formula (I) wherein substituents R6 and R7 taken together with the carbon atoms to which they are bonded form a cyclic structure which may contain an oxygen atom as a ring constituent atom, the cyclic structure forming a 5-4, 5-5, or 5-6 fused bicyclic pyrrolidinyl substituent, the substituent being bonded to a quinolone mother skeleton Q containing a pyridobenzoxazine structure.

  提供了一种具有出色药物特性的喹诺酮合成抗菌剂，它不仅对革兰氏阴性菌具有强烈的抗菌活性，而且对对喹诺酮抗菌剂敏感性较低的革兰氏阳性球菌也具有强烈的抗菌活性，并且具有高安全性和优异的药代动力学。化合物由式(I)或其盐或其水合物表示，具体来说，是式(I)的喹诺酮衍生物，其中取代基R6和R7与它们连接的碳原子一起形成一个环状结构，该环状结构可以包含一个氧原子作为环构成原子，该环状结构形成一个5-4、5-5或5-6融合的双环吡咯烷基取代基，该取代基与含有吡啶并苯并噁嗪结构的喹诺酮母骨架Q连接。
• WO2008/82009
  申请人：——

  公开号：——

  公开（公告）日：——
• FUSED SUBSTITUTED AMINOPYRROLIDINE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2097400B1

  公开（公告）日：2013-07-03
• US8618094B2
  申请人：——

  公开号：US8618094B2

  公开（公告）日：2013-12-31