tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate | 144243-44-7

• 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 (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
• 英文别名: (S)-tert-butyl-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate；(S)-tert-Butyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
• CAS: 144243-44-7
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: LAWPGSGXPGSRTD-NSHDSACASA-N

物化性质

• 沸点：
  403.3±38.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 在 盐酸 、 lithium hydroxide 、 三甲基乙酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 isophthalic acid L-proline L-prolyl-pyrrolidine amide
  参考文献：
  名称：

  New Prolyl Oligopeptidase Inhibitors Developed from Dicarboxylic Acid Bis(l-prolyl-pyrrolidine) Amides

  摘要：

  Isophthalic acid bis(L-prolyl-pyrrolidine) amide is a very potent prolyl oligopeptidase inhibitor, but it has a log P value of -0.2, which is very low for a compound targeted to the brain. Therefore, these types of compounds were further modified to improve the structure-activity relationships, with the focus on increasing the log P value. The inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. The most promising compounds resulted from replacing the pyrrolidinyl. group at the P5 site by cycloalkyl groups, such as cyclopentyl and cyclohexyl groups, and by a phenyl group. These compounds are slightly more potent, and they have a significantly higher log P value. The potency of these compounds was further increased by replacing the pyrrolidinyl group at the P1 site by 2(S)-cyanopyrrolidinyl and 2(S)(hydroxyacetyl)pyrrolidinyl groups.

  DOI：

  10.1021/jm030811o
• 作为产物：
  描述：

  碳酸二叔丁酯 在 sodium hydroxide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Asymmetric induction in the conjugate addition reactions of chiral organo(hetero)cuprates

  摘要：

  DOI：

  10.1021/ja00241a021

文献信息

• α-Aminoamides as ligands in Goldberg amidations
  作者：Aurpon W. Mitra、Marvin M. Hansen、Michael E. Laurila、Stanley P. Kolis、Joseph R. Martinelli

  DOI：10.1016/j.tetlet.2013.09.099

  日期：2013.11

  α-Aminoamides are shown to be useful as ligands in Goldberg amidations. A number of α-aminoamides are examined and the importance of substitution on the α-aminoamides is explored. Acetamide is focused on as the nucleophilic coupling partner due to its low cost, stability and convenience as a protecting group. The initial substrate scope for these catalysts is explored and includes electronically activated

  已显示α-氨基酰胺可用作戈德堡酰胺化中的配体。检查了许多α-氨基酰胺，并探讨了在α-氨基酰胺上取代的重要性。乙酰胺由于其低成本，稳定性和方便性而作为保护基团而成为亲核偶联伴侣。探索了这些催化剂的初始底物范围，包括电子活化和失活的芳基溴化物，但是o-取代的芳基溴化物是有问题的。
• Design of an Organocatalyst for the Enantioselective Diels−Alder Reaction with α-Acyloxyacroleins
  作者：Kazuaki Ishihara、Kazuhiko Nakano

  DOI：10.1021/ja053368a

  日期：2005.8.1

  derived from H-l-Phe-l-Leu-N(CH2CH2)2. The enantioselective Diels-Alder reaction of 5-(benzyloxymethyl)cyclopentadiene, cyclopentadiene, cyclohexadiene, 2,3-dimethylbutadiene, and isoprene with alpha-(p-methoxybenzoyloxy)acrolein catalyzed by the above chiral ammonium salt (2.5-20 mol %) at -20-22 degrees C gave the corresponding adducts with 83, 83, 91, 92, and 88% ee, respectively.

  我们已经实现了第一个对映选择性有机催化 Diels-Alder 反应，α 取代的丙烯醛，例如 α-酰氧基丙烯醛，不仅是环状二烯，还包括无环二烯。α-酰氧基丙烯醛可用作α-卤代丙烯醛的合成等价物。本催化剂可由五氟苯磺酸(2.5-3.0当量)和衍生自Hl-Phe-1-Leu-N(CH2CH2)2的手性三胺(1当量)原位制备。5-(苄氧基甲基)环戊二烯、环戊二烯、环己二烯、2,3-二甲基丁二烯和异戊二烯与α-(对甲氧基苯甲酰氧基)丙烯醛在上述手性铵盐(2.5-20 mol %)催化下的对映选择性Diels-Alder反应-20-22 摄氏度产生相应的加合物，分别为 83、83、91、92 和 88% ee。
• [EN] NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS D'AMIDE SUBSTITUÉS BÉTULINIQUES UTILISÉS COMME INHIBITEURS DU VIH
  申请人：HETERO RESEARCH FOUNDATION

  公开号：WO2017017630A1

  公开（公告）日：2017-02-02

  The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

  本发明涉及新的取代苦杏仁酸酰胺化合物的化学式(I)；以及其药用盐，其中R1、R2、R3、R4、R5、R6、R7、R8、X、Y、Z1、Z2、Z3和在此定义的化学式(II)。该发明涉及新的取代苦杏仁酸酰胺衍生物、相关化合物和药物组合物，用于治疗病毒性疾病，特别是HIV介导的疾病。
• Easily removable olefin metathesis catalysts
  作者：Krzysztof Skowerski、Celina Wierzbicka、Grzegorz Szczepaniak、Łukasz Gułajski、Michał Bieniek、Karol Grela

  DOI：10.1039/c2gc36015b

  日期：——

  A small family of olefin metathesis catalysts bearing a polar quaternary ammonium group is described. The presence of this group allows for efficient separation of ruthenium impurities after the reaction. Application of catalysts 9 and 11 leads to organic products of high purity, which exhibit surprisingly low ruthenium contamination levels (usually below 5 ppm) after a simple and inexpensive purification step.

  描述了一类带有极性季铵盐官能团的小型烯烃复分解催化剂家族。该官能团的存在使得反应后能够高效分离铑杂质。应用催化剂9和11，能够得到高纯度的有机产物，在简单廉价的后处理后，显示出了令人惊讶的低铑污染水平（通常低于5ppm）。
• Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes
  申请人：——

  公开号：US20030195190A1

  公开（公告）日：2003-10-16

  Novel amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes, use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds, and a method of treatment employing these compounds and compositions. The compounds show a high and selective binding affinity to the histamine H3 receptor indicating histamine H3 receptor antagonistic, inverse agonistic or agonistic activity. As a result, the compounds are useful for the treatment of diseases and disorders related to the histamine H3 receptor.

  氨基烷基取代的氮杂环戊烷、吡咯烷、哌啶和环庚烷的新型酰胺，以这些化合物作为药物组合物的用途，包含这些化合物的药物组合物，以及使用这些化合物和组合物进行治疗的方法。这些化合物显示出高度和选择性地结合到组胺H3受体，表明具有组胺H3受体拮抗、逆拮抗或激动活性。因此，这些化合物可用于治疗与组胺H3受体相关的疾病和疾病。