ethyl (2'S)-4-(N-(tert-Butoxycarbonyl)pyrrolidin-2'-yl)-3-oxabutanoate | 132127-47-0

• 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: ethyl (2'S)-4-(N-(tert-Butoxycarbonyl)pyrrolidin-2'-yl)-3-oxabutanoate
• 英文别名: (2S)-2-(((ethoxycarbonyl)methoxy)methyl)pyrrolidin-1-carboxylic acid tert-butyl ester；(2S)-2-(((ethoxycarbonyl)methoxy)methyl)pyrrolidin-1-carboxylic acid tert-butylester；tert-butyl (2S)-2-[(2-ethoxy-2-oxoethoxy)methyl]pyrrolidine-1-carboxylate
• CAS: 132127-47-0
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: NPSILQRSKNCBKB-NSHDSACASA-N

物化性质

• 沸点：
  375.7±12.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2'S)-4-(N-(tert-Butoxycarbonyl)pyrrolidin-2'-yl)-3-oxabutanoate 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-([N-methyl-N-{(1R)-1-(N-methyl-N-[(1R)-1-(methylcarbamoyl)-2-phenylethyl]carbamoyl)-2-(2-naphthyl)ethyl}carbamoyl]methoxymethyl)pyrrolidine-1-carboxylic acid tert-butylester
  参考文献：
  名称：

  Synthesis and in vitro characterization of new growth hormone secretagogues derived from ipamorelin with dipeptidomimetic N-terminals

  摘要：

  The structural requirements for N-terminal features for the minimal structure of growth hormone secretagogues derived from ipamorelin are investigated. It is found, that incorporation of nonpolar peptidomimetic amino acids at the N-terminal can replace the Aib-His moiety and lead to compounds with high in vitro potency with respect to their growth hormone secretagogue properties. New unnatural amino acids with double bonds, ether-linkages, and 1,3-phenylene-moieties in the backbone proved to be valuable dipeptidomimetics. Using them, growth hormone secretagogues with high potencies were obtained. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80086-5
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.75h， 生成 ethyl (2'S)-4-(N-(tert-Butoxycarbonyl)pyrrolidin-2'-yl)-3-oxabutanoate
  参考文献：
  名称：

  Synthesis of proline-valine pseudodipeptide enol lactones, serine protease inhibitors

  摘要：

  Pseudodipeptides of proline-valine that incorporate protio or halo enol lactone moieties have been synthesized from common acetylenic acid precursors; in each case, two diasteromers were prepared in enantiomerically pure form. The preparation began with isomeric propargylic alcohols derived from L-prolinal, which are further elaborated into the methyleneoxy valine pseudodipeptide analogues via an oxalactam intermediate. Stereochemical assignments were made by comparisons of nuclear Overhauser enhancement factors. The pseudodipeptide acetylenic acids could by cyclized to the protio enol lactones by mercuric salts and could be elaborated to tetrapeptide analogues either before or after cyclization. The relative stability of the two diastereomeric enol lactone systems toward intramolecular acyl transfer could be rationalized by molecular mechanics energy calculations on ground-state and tetrahedral intermediates believed to be involved in the reaction. While the halo enol lactones derived from the pseudotetrapeptides proved to be very unstable, they could be prepared from the n-butyl carbamate derivatives of the dipeptide. An evaluation of these protio and halo enol lactone systems as inhibitors of serine proteases will be discussed elsewhere.

  DOI：

  10.1021/jo00008a011

文献信息

• Compounds with growth hormone releasing properties
  申请人：Novo Nordisk A/S

  公开号：US05977178A1

  公开（公告）日：1999-11-02

  Compounds of peptide mimetic nature having the general formula I ##STR1## wherein a and b are independently 1 or 2, R.sup.1 and R.sup.2 are independently H or C.sub.1-6 alkyl, G and J are independently, inter alia, aromats, and D and E are independently several different groups are growth hormone secretagogous with improved bioavailability.

  具有一般式I的肽类模拟化合物##STR1##，其中a和b独立地为1或2，R.sup.1和R.sup.2独立地为H或C.sub.1-6烷基，G和J独立地为芳香族等，D和E独立地为几种不同的基团，具有改善生物利用度的生长激素分泌素。
• [EN] 7-ARYL-3,9-DIAZABICYCLO(3.3.1)NON-6-ENE DERIVATIVES AND THEIR USE AS RENIN INHIBITORS IN THE TREATMENT OF HYPERTENSION, CARDIOVASCULAR OR RENAL DISEASES<br/>[FR] DERIVES DE 7-ARYL-3,9-DIAZABICYCLO(3.3.1)NON-6-ENE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE RENINE DANS LE TRAITEMENT DE L'HYPERTENSION, DE MALADIES CARDIOVASCULAIRES OU RENALES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2003093267A1

  公开（公告）日：2003-11-13

  The invention relates to novel 3,9-diazabicyclo[3.3.1]nonene derivatives of formula (I) and related compounds and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as inhibitors or renin.

  该发明涉及新型3,9-二氮杂双环[3.3.1]壬烯衍生物（I）及相关化合物，以及它们作为药物组合物中活性成分的用途。该发明还涉及相关方面，包括制备这些化合物的过程、含有这些化合物中的一个或多个的药物组合物，尤其是它们作为肾素抑制剂的用途。
• [EN] COMPOUNDS WITH GROWTH HORMONE RELEASING PROPERTIES<br/>[FR] COMPOSES AVEC DES PROPRIETES DE LIBERATION DE L'HORMONE DE CROISSANCE
  申请人：NOVO NORDISK A/S

  公开号：WO1997023508A1

  公开（公告）日：1997-07-03

  (EN) Compounds of peptide mimetic nature having general formula (I), wherein a and b are independently 1 or 2, R1 and R2 are independently H or C1-6alkyl, G and J are independently, inter alia, aromats, and D and E are independently several different groups, are growth hormone secretagogous with improved bioavailability.(FR) L'invention concerne un peptide de nature mimétique ayant la formule générale (I). Dans cette formule, a et b sont, d'une manière indépendante 1 ou 2, R1 et R2 sont, d'une manière indépendante H ou C1-6 alkyle, G et J sont, d'une manière indépendante, entre autres, des groupes aromatiques et D et E sont, d'une manière indépendante, plusieurs groupes différents. Ces peptides favorisent la sécrétion de l'hormone de croissance et améliorent sa biodisponibilité.

  化合物具有类肽类似物性质的通式(I)，其中a和b独立地为1或2，R1和R2独立地为H或C1-6烷基，G和J独立地为芳香族等基团，D和E独立地为多种不同基团，具有改善生物利用度的生长激素分泌剂。
• InCl3 catalyzed carbene insertion into O–H bonds: efficient synthesis of ethers
  作者：Palakodety Radha Krishna、Y. Lakshmi Prapurna、Munagala Alivelu

  DOI：10.1016/j.tetlet.2011.04.099

  日期：2011.7

  An efficient InCl3 mediated insertion of the carbene fragment (:CHCO2Et), generated in situ from ethyl diazoacetate into O-H bond of a series of saturated and unsaturated alcohols under mild conditions has been developed to afford the corresponding ethers as exclusive products in good to high yields (70-95%) and in shorter reaction times. In the case of unsaturated alcohols, the reaction proceeded with unprecedented selectivity resulting in ethers as the only products and in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
• REED, PETER E.;KATZENELLENBOGEN, JOHN A., J. ORG. CHEM., 56,(1991) N, C. 2624-2634
  作者：REED, PETER E.、KATZENELLENBOGEN, JOHN A.

  DOI：——

  日期：——