ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate | 126400-92-8

• 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: ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate
• 英文别名: (3S)-ethyl N-benzyloxycarbonyl-3-aminobutanoate；ethyl (3S)-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 126400-92-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: QHXYGPNSRQLONO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (S)-3-Cbz-氨基丁酸
  参考文献：
  名称：

  Candida antarctica lipase catalyzed resolution of ethyl (±)-3-aminobutyrate

  摘要：

  Candida antarctica lipase efficiently catalyzes acetylation and hydrolysis of ethyl (+/-)-3-aminobutyrate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00487-9
• 作为产物：
  描述：

  3-氨基丁酸乙酯 在 Candida antarctica lipase (CAL-SP 435) 、 sodium carbonate 、 乙酸乙酯 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}butanoate
  参考文献：
  名称：

  Candida antarctica lipase catalyzed resolution of ethyl (±)-3-aminobutyrate

  摘要：

  Candida antarctica lipase efficiently catalyzes acetylation and hydrolysis of ethyl (+/-)-3-aminobutyrate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00487-9

文献信息

• Studies on angiotensin converting enzyme inhibitors. III. 2-Carboxyethylcarbamoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives.
  作者：KIMIAKI HAYASHI、KENICHI NUNAMI、KAZUO SAKAI、YASUHIKO OZAKI、JYOJI KATO、KEIZO KINASHI、NAOTO YONEDA

  DOI：10.1248/cpb.33.2011

  日期：——

  (3S)-2-[N-Substituted N-(2-carboxyethyl) carbamoyl]-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid derivaties (8a-d and 12a-t) and their monoester compounds (13a-k) were synthesized by condensation of (3S)-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylates (6a, b), 3-aminopropionates (5a, b or 10a-m) and phosgene, followed by deprotection of ester groups. Their in vitro angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationship is discussed. Some of the N-ethylcarbamoyl analogs (12h, 12j, 12k, 12l and 12o), which had hydrophobic substituents (C8H17-C12H25, CH2CH2Ph) at the α-position to the carboxyl group in the side chain, showed potent in vitro ACE inhibitory activities with IC50 values of 4.0-8.8×10-9M. The monoesters 13e, 13h, and 13i reduced the systolic blood pressure by more than 30 mmHg in spontaneously hypertensive rats (SHR) at an oral dose of 50mg/kg.

  (3S)-2-[N-取代的N-(2-羧乙基)氨基甲酸]-1, 2, 3, 4-四氢异喹啉-3-羧酸衍生物 (8a-d 和 12a-t) 及其单酯化合物 (13a-k) 通过 (3S)-1, 2, 3, 4-四氢异喹啉-3-羧酸酯 (6a, b)、3-氨基丙酸酯 (5a, b 或 10a-m) 和氯仿的缩合反应合成，随后去保护酯基。评估了它们在体外的血管紧张素转化酶 (ACE) 抑制活性及抗高血压效果，并讨论了结构-活性关系。一些具有疏水取代基（C8H17-C12H25，CH2CH2Ph）在侧链α位与羧基相邻的N-乙基氨基甲酸类似物 (12h, 12j, 12k, 12l 和 12o) 显示出强大的体外ACE抑制活性，IC50值为4.0-8.8×10^-9M。单酯化合物13e、13h和13i在口服剂量为50mg/kg时，能使自发性高血压大鼠 (SHR) 的收缩压下降超过30 mmHg。
• Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones
  作者：Brad E. Sleebs、Andrew B. Hughes

  DOI：10.1021/jo0700326

  日期：2007.4.1

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.
• Synthesis of <i>N</i>-Methyl-<i>N</i>-{(1<i>S</i>)-1-[(3<i>R</i>)-pyrrolidin-3-yl]ethyl}amine
  作者：Thomas J. Fleck、William W. McWhorter,、Richard N. DeKam、Bruce A. Pearlman

  DOI：10.1021/jo0349633

  日期：2003.12.1

  N-Methyl-N-(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine (1)(1) is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-methyl[(1S)-1-phenylethyl]amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).
• Candida antarctica lipase catalyzed resolution of ethyl (±)-3-aminobutyrate
  作者：Víctor M. Sánchez、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/s0957-4166(96)00487-9

  日期：1997.1

  Candida antarctica lipase efficiently catalyzes acetylation and hydrolysis of ethyl (+/-)-3-aminobutyrate. (C) 1997, Elsevier Science Ltd.