tert-butyl (3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate | 915302-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
• 英文别名: (3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester；tert-Butyl(3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
• CAS: 915302-95-3
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: ZRQKGZVVLQGYDQ-ACJLOTCBSA-N

物化性质

• 沸点：
  422.7±45.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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 (3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 tert-butyl (3S)-4-(2-hydroxyethyl)-3-methyl-5-oxo-1-[(R)-1-phenylethyl]pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Novel 7-[7-Amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-8-methoxyquinolines with Potent Antibacterial Activity against Respiratory Pathogens

  摘要：

  Novel 7-[7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]- 8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 2a and 2b were designed and synthesized to obtain potent antibacterial drugs for the treatment of respiratory tract infections. Among these, compound 2a possessing (S)-configuration for the asymmetrical carbon on the pyrolidine moiety at the C-7 position of the quinolone scaffold exhibited potent in vitro antibacterial activity against respiratory pathogens including Gram-positive (Streptococcus pneumoniae and Staphylococcus aureus), Gram-negative (Haemophilus influenzae and Moraxcella catarrhalis), and atypical strains (Chalmydia pneumoniae and Mycoplasma pneumoniae), as well as multidrug-resistant Streptococcus pneumoniae and quinolone-resistant and methicillin-resistant Staphylococcus aureus). Furthermore, compound 2a showed excellent in vivo activity against the experimental murine pneumonia model due to multidrug resistant Streptococcus pneumoniae (MDRSP) and favorable profiles in preliminary toxicological and nonclinical pharmacokinetic studies.

  DOI：

  10.1021/jm301650g
• 作为产物：
  描述：

  tert-butyl 3-(hydroxymethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate 在 三丁基膦 、 二苯二硫醚 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.0h， 以12%的产率得到tert-butyl (3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
  参考文献：
  名称：

  新型7的设计，合成和生物学评价- [（3-如，7为）-3一个-Aminohexahydropyrano [3,4 Ç ]吡咯-2（3 H ^） -基] -8- methoxyquinolines与抗强抗菌活性呼吸道病原体

  摘要：

  新颖7 - [（3-如，7为）-3一个-aminohexahydropyrano [3,4 Ç ]吡咯-2（3 H ^） -基] -6-氟-1 - [（1 - [R，2小号）-2-设计并合成了[氟代环丙基] -8-甲氧基-4-氧代-1,4-二氢喹啉-3-羧酸5（DS21412020），以获得用于治疗呼吸道感染的有效抗菌药物。在喹诺酮骨架的C-7位置的吡咯烷部分上具有反式吡喃糖环的化合物5对呼吸道病原体表现出有效的体外抗菌活性，包括耐喹诺酮和耐甲氧西林金黄色葡萄球菌（QR - MRSA）和耐喹诺酮类大肠杆菌（QR- E. coli）。此外，由于对青霉素具有抗性的肺炎链球菌（PRSP），化合物5对实验性鼠肺炎模型表现出体内活性，并且在初步的毒理学和非临床药代动力学研究中显示出良好的特性。特别地，与先前合成的氨基甲酸酯型化合物4相比，化合物5的亲脂性和碱性降低。 导致人类“走走走走”（hERG）

  DOI：

  10.1021/acs.jmedchem.8b00644

文献信息

• Tri-, tetra-substituted-3-aminopyrrolidine derivative
  申请人：Takahashi Hisashi

  公开号：US20060264428A1

  公开（公告）日：2006-11-23

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by following formula (I): wherein R 1 and R 2 represent hydrogen atom, or the like; R 3 represents an alkyl group containing 1 to 6 carbon atoms, or the like; R 4 and R 5 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like, with the proviso that R 4 and R 5 do not simultaneously represent hydrogen atom; or the substituents R 4 and R 5 together represent (a) a 3- to 6-membered cyclic structure including the carbon atom shared by R 4 and R 5 to form a spirocyclic structure with the pyrrolidine ring; R 6 and R 7 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like; R 8 represents a halogen-substituted alkyl group containing 1 to 6 carbon atoms, or the like; X 1 represents hydrogen atom or a halogen atom; A represents nitrogen atom or a moiety represented by formula (II):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，对革兰氏阳性和革兰氏阴性细菌均表现出广谱和强效的抗菌活性，并且具有很高的安全性。所提供的化合物由以下式（I）表示： 其中R1和R2代表氢原子，或类似物；R3代表含有1至6个碳原子的烷基基团，或类似物；R4和R5独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物，但R4和R5不同时代表氢原子；或取代基R4和R5一起代表（a）包括由R4和R5共享的碳原子形成螺环结构与吡咯烷环形成螺环结构的3至6成员环结构；R6和R7独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物；R8代表含有1至6个碳原子的卤代烷基基团，或类似物；X1代表氢原子或卤原子；A代表氮原子或由式（II）表示的基团。
• TRI-, TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVE
  申请人：TAKAHASHI Hisashi

  公开号：US20090253726A1

  公开（公告）日：2009-10-08

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by formula (I):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，具有广谱和强大的抗菌活性，对革兰氏阳性和革兰氏阴性细菌均有作用，并且非常安全。所提供的化合物由式（I）表示。
• METHOD FOR PRODUCING ASYMMETRIC TETRASUBSTITUTED CARBON ATOM-CONTAINING COMPOUND
  申请人：Tani Yuichiro

  公开号：US20090054648A1

  公开（公告）日：2009-02-26

  The invention provides an industrial method for producing a spiroaminopyrrolidone derivative, which is an intermediate for producing a quinolone antibacterial agent. The invention provides a method for producing a compound represented by formula (2): (wherein n is an integer of 2 to 5; R 1 represents a (substituted) alkyl group or a (substituted) aryl group; and R 2 represents a (substituted) alkoxycarbonyl group, a (substituted) aralkyloxycarbonyl group, a (substituted) aliphatic acyl group, or a (substituted) aromatic acyl group), which includes treating a compound represented by formula (1): (wherein n, R 1 , and R 2 are the same as defined above; and R 3 represents a hydrogen atom, a (substituted) alkyl group, or a (substituted) aralkyl group) under a hydrogen gas atmosphere in the presence of a metallic catalyst.

  本发明提供了一种工业方法，用于生产螺环氨基吡咯烷衍生物，该衍生物是生产喹诺酮类抗菌剂的中间体。本发明提供了一种生产由式（2）表示的化合物的方法：（其中n是2至5的整数；R1表示（取代）烷基或（取代）芳基；R2表示（取代）烷氧羰基，（取代）芳基烷氧羰基，（取代）脂肪酰基或（取代）芳香酰基），其包括在金属催化剂存在下，在氢气气氛下处理由式（1）表示的化合物：（其中n，R1和R2如上定义；R3表示氢原子，（取代）烷基或（取代）芳基烷基）。
• PROCESS FOR PREPARATION OF TETRASUBSTITUTED 5-AZASPIRO[2.4]- HEPTANE DERIVATIVES AND OPTICALLY ACTIVE INTERMEDIATES THEREOF
  申请人：Takahashi Hisashi

  公开号：US20090270637A1

  公开（公告）日：2009-10-29

  The present invention provides a method for effectively producing an optically active form of tetrasubstituted-5-azaspiro[2.4]heptane derivative, which serves as a useful production intermediate for quinolonecarboxylic acid antibacterial agents, and intermediates for the derivative. The present invention is directed to a method for producing a compound (VII) according to the following scheme.

  本发明提供了一种有效生产四取代-5-氮杂螺[2.4]庚烷衍生物的光学活性形式的方法，该方法作为喹诺酸类抗菌剂的有用生产中间体以及该衍生物的中间体。本发明是针对按照以下方案生产化合物（VII）的方法。
• Antifungal bicyclic hetero ring compounds
  申请人：Daiichi Sankyo Company, Limited

  公开号：US07737166B2

  公开（公告）日：2010-06-15

  A 1,6-β-glucan synthetase inhibitor is provided, having potent growth inhibition and having excellent safety. A compound is provided, capable of expressing in a wide spectral range and specifically or selectively, an antifungal effect based on its functional mechanism of 1,6-β-glucan synthesis inhibition. Also provided is a drug, a salt or hydrate thereof, especially an antifungal that contains the compound. Concretely, provided is a compound of the following formula (I), its salt or hydrate, and a drug or antifungal containing, as the active ingredient, the compound, its salt or hydrate:

  提供了一种1,6-β-葡聚糖合成酶抑制剂，具有强效的生长抑制作用和优异的安全性。提供了一种化合物，能够在广泛的光谱范围内表达，并基于其1,6-β-葡聚糖合成抑制的功能机制，具有特异性或选择性的抗真菌作用。此外，还提供了一种药物、其盐或水合物，特别是含有该化合物的抗真菌药物。具体而言，提供了以下式（I）的化合物、其盐或水合物，以及含有该化合物、其盐或水合物作为活性成分的药物或抗真菌药物：