1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate | 114676-91-4

• 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: 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate
• 英文别名: (2S,4R)-1-tert-butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate
• CAS: 114676-91-4
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: GDGVOGGJKRMIOF-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 18-冠醚-6 、 四丁基氟化铵 、 三乙胺 、 二异丙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 生成 tert-butyl (2R,4S)-4-cyano-2-(methoxymethyl)-2-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 2,2-Disubstituted Pyrrolidine-4-carboxylic Acid Derivatives and Their Incorporation into β-Peptide Oligomers

  摘要：

  We have recently shown that members of a new class of P-peptides, containing 2,2-disubstituted pyrrolidine-4-carboxylic acid residues, display discrete conformational preferences despite the impossibility of internal hydrogen bonding (Huck et al. J. Am. Chem. Soc. 2003, 125, 9035). Here we describe the synthesis of a variety of 2,2-disubstituted pyrrolidine-4-carboxylic derivatives that bear a diverse set of side chains and protecting groups suitable for oligomer synthesis. In addition, we discuss coupling methods for construction of oligomers in solution and on solid phase. Nonhydrogen bonded foldamers such as those generated from 2,2-disubstituted pyrrolidine-4-carboxylic acids may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.

  DOI：

  10.1021/jo048639z
• 作为产物：
  描述：

  L-羟基脯氨酸 在 咪唑 、 氯化亚砜 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent

  摘要：

  一系列α-取代硝基烯与醛在有机催化不对称Michael反应中被应用。得到了产率良好（高达86%）且立体选择性良好的γ-硝基羰基产物（高达96% ee和24:1 dr）。经过硝基还原后再进行分子内还原胺化，成功合成了多种新型光学活性的2,4-二取代吡咯烷化合物。

  DOI：

  10.1039/c3cc40583d

文献信息

• Regioselective Synthesis of Nitrones by Decarboxylative Oxidation of<i>N</i>-Alkyl-<i>α</i>-amino Acids and Application to the Synthesis of 1-Azabicyclic Alkaloids
  作者：Hiroaki Ohtake、Yasushi Imada、Shun-Ichi Murahashi

  DOI：10.1246/bcsj.72.2737

  日期：1999.12

  were prepared by catalytic oxidation of the corresponding chiral pyrrolidines in a regioselective manner. These chiral cyclic nitrones, 17 and 45 are versatile intermediates for the synthesis of optically active nitrogen heterocycles, since stereoselective additions of carbon nucleophiles to these chiral nitrones can be readily performed. Typically, ZnI2-mediated addition of ketene t-butyldimethylsilyl

  在相转移条件下用 30% H2O2 溶液钨酸盐催化氧化 N-烷基-α-氨基酸，区域选择性地以良好的产率得到硝酮。使用该方法，实现了（R）-和（S）-4-（叔丁基二甲基甲硅烷氧基）-1-吡咯啉N-氧化物（（R）-17a和（S）-17a）的立体发散合成。此外，(R)-和(S)-3-(叔丁基二甲基甲硅烷氧基)-1-吡咯啉N-氧化物((R)-45和(S)-45)是通过相应手性吡咯烷的催化氧化制备的区域选择性方式。这些手性环状硝酮 17 和 45 是合成光学活性氮杂环的通用中间体，因为可以很容易地将碳亲核试剂立体选择性加成到这些手性硝酮上。通常，ZnI2 介导的乙烯酮叔丁基二甲基甲硅烷基甲基缩醛 (29a) 与 (R)-17a 的加成得到顺式加合物，(2R,4R)-[1,4-双(叔丁基二甲基甲硅烷氧基)吡咯烷-2-基]乙酸甲酯(cis-30)。相比之下，将乙炔锂 34 添加到硝酮 (R)-17a 中得到
• Substituted Imidazopyridines as HDM2 Inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20140179680A1

  公开（公告）日：2014-06-26

  The present invention provides substituted imidazopyridines as described herein or a pharmaceutically acceptable salt or solvate thereof. The representative compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and potential methods of treating cancer using the same.

  本发明提供了如本文所述的取代咪唑吡啶或其药用可接受的盐或溶剂。代表性化合物可用作HDM2蛋白的抑制剂。还公开了包括上述化合物的药物组合物以及使用它们治疗癌症的潜在方法。
• New methods and reagents in organic synthesis. 92. A stereoselective synthesis of tilivalline and its analogs
  作者：Shigehiro Mori、Tomoyasu Ohno、Hiroshi Harada、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)80968-6

  日期：——

  Tilivalline (1a), a metabolite from Klebsiella pneumoniae var. oxytoca, and its derivatives 1 have been efficiently and stereoselectively synthesized from diphenyl phosphorazidate, the 2-oxazoline 2, the L-proline derivatives 5, and indole; the key step is a Mannich type intramolecular cyclization accompanied with completely stereoselective introduction of indole. Furthermore, 11-substituted 5H- pyrrolo[2

  Tilivalline（1a），肺炎克雷伯菌的一种代谢产物。催产素及其衍生物1已由叠氮基磷酸二苯酯，2-恶唑啉2，L-脯氨酸衍生物5和吲哚有效地和立体选择性地合成；关键步骤是伴随完全立体选择性引入吲哚的曼尼希型分子内环化反应。此外，通过使用这种新的曼尼希型环化反应，还由乙缩醛酰胺9a和各种亲核试剂合成了11个取代的5 H-吡咯并[2,1- c ] [1,4]苯并二氮杂-5-酮（16）。。
• [EN] SPIRO AMINO COMPOUNDS SUITABLE FOR THE TREATMENT OF INTER ALIA SLEEP DISORDERS AND DRUG ADDICTION<br/>[FR] COMPOSÉS SPIRO-AMINIQUES CONVENANT AU TRAITEMENT, NOTAMMENT, DES TROUBLES DU SOMMEIL ET DE LA PHARMACODÉPENDANCE
  申请人：ROTTAPHARM SPA

  公开号：WO2011006960A1

  公开（公告）日：2011-01-20

  The invention concerns a spiro-amino compound of Formula (Vl) wherein m is 1 or 2 or 3, n is 1 or 2, R is selected from a 5- or 6-membered aromatic ring and a 5- or 6-membered heteroaromatic ring comprising 1 to 3 heteroatoms selected from S, O e N, such ring being substituted with one or two substituents selected from the group consisting of (C1-C3)alkyl, halogen, (C3-C5)cycloalkyloxy, (C1-C3)alkylcarbonyl, phenyl optionally substituted with one or more halogen atoms, a 5- or 6-membered heterocycle comprising at least one nitrogen atom; P is a substituent Q or COQ, wherein Q is selected from the group consisting of phenyl, pyridil, pyrimidil, quinolyl, isoquinolyl, quinoxalyl, benzofuranyl, imidazotriazolyl, being such Q optionally substituted with one or more substituents selected from the group consisting of (C1-C3)alkyl, halogen, trifluoromethyl, carbammido, methylcarbammido, carboxy, methylcarboxy or a pharmaceutically acceptable salt thereof.

  本发明涉及一种式(Vl)的螺环氨基化合物，其中m为1或2或3，n为1或2，R选自5-或6-成环的芳香环和5-或6-成环的杂芳香环，包含1至3个选自S、O和N的杂原子，该环被1个或2个选自(C1-C3)烷基、卤素、(C3-C5)环烷基氧基、(C1-C3)烷基羰基、可选地用1个或多个卤素原子取代的苯基、至少含有一个氮原子的5-或6-成环杂环所取代；P是取代基Q或COQ，其中Q选自苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、喹喔啉基、苯并呋喃基、咪唑三唑基，该Q可选项地被1个或多个选自(C1-C3)烷基、卤素、三氟甲基、碳酰胺、甲基碳酰胺、羧基、甲基羧基的取代基所取代，或其药用可接受盐。
• PYRIMIDINE COMPOUNDS AS DELTA OPIOID RECEPTOR MODULATORS
  申请人：COATS STEVEN J.

  公开号：US20110105520A1

  公开（公告）日：2011-05-05

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula I as follows: wherein R 1 , R 2 , R 3 , and L, A, and R a are defined herein.

  公开了用于治疗各种疾病、综合征、状况和失调，包括疼痛的化合物、组合物和方法。这些化合物由以下式I表示： 其中R1、R2、R3和L、A、Ra在本文中定义。