(2S,5S)-5-苯基吡咯烷-2-甲酸乙酯 | 166941-66-8

• 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
• 中文名称: (2S,5S)-5-苯基吡咯烷-2-甲酸乙酯
• 中文别名: (5S)-5-苯基-L-脯氨酸乙酯
• 英文名称: α-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine
• 英文别名: Ethyl (2S,5S)-5-phenylprolinate；(2S,5S)-ethyl 5-phenylpyrrolidine-2-carboxylate；ethyl (2S,5S)-5-phenylpyrrolidine-2-carboxylate
• CAS: 166941-66-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: BJOUEZQMVVKCPC-RYUDHWBXSA-N

物化性质

• 沸点：
  318.9±42.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲氧基吡咯烷-1,2-二羧酸-(2S)-1-叔丁基-2-乙酯 在 copper(I) bromide dimethylsulfide complex 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2S,5S)-5-苯基吡咯烷-2-甲酸乙酯
  参考文献：
  名称：

  Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates

  摘要：

  Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.

  DOI：

  10.1021/jo00121a020

文献信息

• trans-2,5-Disubstituted pyrrolidines: rapid stereocontrolled access from sulfones
  作者：Mark G. Moloney、Terry Panchal、Richard Pike

  DOI：10.1039/b611583g

  日期：——

  A direct and versatile route for the reliable synthesis of trans-2,5-disubstituted pyrrolidines from pyroglutamic acid is reported, which can be conducted at scale and without chromatographic purification of key intermediates.

  从焦谷氨酸可靠地合成反式2，5-二取代的吡咯烷类化合物的直接和通用途径已被报道，该方法可以大规模进行，而无需色谱纯化关键中间体。
• Convenient synthesis of C-aza-2,3-dideoxynucleosides
  作者：Atsuya Momotake、Hideo Togo、Masataka Yokoyama

  DOI：10.1039/a900689c

  日期：——

  1-Aryl-1,2,3,4-tetradeoxy-1,4-imino-D-pentitols 5 and 9f are easily synthesized from N-Boc-L-pyroglutamate 1 via a successive procedure involving regioselective ring-opening, recyclization with dehydration, stereoselective reduction, and reduction of the ester group. Their structures are determined mainly by X-ray crystallography and NMR measurements. Their bioassay is also described.

  1- 芳基-1,2,3,4-四甲氧基-1,4-亚氨基-D-戊醇 5 和 9f 是由 N-Boc-L-pyroglutamate 1 通过区域选择性开环、脱水再化、立体选择性还原和酯基还原等连续过程轻松合成的。它们的结构主要是通过 X 射线晶体学和核磁共振测量确定的。此外，还介绍了它们的生物测定方法。
• THIOPHENE DERIVATIVES AS PPAR AGONISTS I
  申请人：Ayscough Andrew

  公开号：US20100063065A1

  公开（公告）日：2010-03-11

  The invention discloses compounds of formula (I); wherein: R is a carboxylic acid or a derivative thereof; R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, halo or trihalomethyl; R 2 is aryl, heteroaryl, arylalkyl or heteroarylalkyl; R 3 is H or F; and L is a linking group comprising a chain of from 2 to 8 atoms linking R and the carbonyl group (A); and pharmaceutically acceptable derivatives thereof, useful for treating disorders mediated by peroxisome-proliferator-activated receptor (PPAR) subtype δ (PPARδ). The compounds of the invention are therefore useful in the treatment of metabolic syndrome, obesity, type-II diabetes, dyslipidemia, wound healing, inflammation, neurodegenerative disorders and multiple sclerosis.

  本发明揭示了式(I)的化合物;其中：R是羧酸或其衍生物; R1是烷基，烯基，炔基，环烷基，烷氧基，烷硫基，卤素或三卤甲基; R2是芳基，杂环芳基，芳基烷基或杂环芳基烷基; R3是H或F; L是一个链接基团，包括从2到8个原子的链连接R和羰基(A);以及其药学上可接受的衍生物，用于治疗通过过氧化物酶体增殖物激活受体(PPAR)亚型δ (PPARδ)介导的疾病。因此，本发明的化合物在代谢综合征、肥胖症、2型糖尿病、脂质代谢异常、伤口愈合、炎症、神经退行性疾病和多发性硬化症的治疗中有用。
• Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates
  作者：Ivan Collado、Jesus Ezquerra、Concepcion Pedregal

  DOI：10.1021/jo00121a020

  日期：1995.8

  Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents. The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates. The stereochemistry is controlled by the formation of a RCu-pi complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.