1-tert-butyl 2-methyl 2-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate | 112348-45-5

• 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 2-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate
• 英文别名: 1-tert-butyl 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate；N-Boc-2-propenylpyrrolidin-2-carboxylic acid methyl ester；(+/-)-α-allyl N-Boc-proline methyl ester；2-allylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester；N-(tert-butyloxycarbonyl)-2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine；1-(Tert-butyl) 2-methyl 2-allylpyrrolidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl 2-prop-2-enylpyrrolidine-1,2-dicarboxylate
• CAS: 112348-45-5
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: VEYTWFFJGOYPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl 2-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以100%的产率得到2-(methoxycarbonyl)-2-(2-propenyl)pyrrolidine hydrochloride
  参考文献：
  名称：

  Design and synthesis of potential DNA cross-linking reagents based on the anthramycin class of minor groove binding compounds

  摘要：

  DOI：

  10.1021/jo00238a004
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 在 三乙胺 、 lithium diisopropyl amide 作用下， 生成 1-tert-butyl 2-methyl 2-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  (3R,7aS)-3-(TRICHLOROMETHYL)TETRAHYDROPYRROLO[1,2-C]OXAZOL-1(3H)-ONE: AN AIR AND MOISTURE STABLE REAGENT FOR THE SYNTHESIS OF OPTICALLY ACTIVE a-BRANCHED PROLINES

  摘要：

  DOI：

  10.15227/orgsyn.086.0262

文献信息

• Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
  作者：Tynchtyk Amatov、Martin Gebauer、Radek Pohl、Ivana Cisařová、Ullrich Jahn

  DOI：10.1080/10715762.2016.1223295

  日期：2016.11.1

  A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3*2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature

  六氟磷酸铁或Mn（OAc）3 * 2H2O / Cu（OTf）2系统介导的官能化二酮哌嗪的直接氧化环化反应，描述了烯丙基桥联二酮哌嗪生物碱的二氮杂双环[2.2.2]辛烷核心的新方法。根据底物的取代方式和氧化条件（例如温度或持久性自由基TEMPO的存在与否），发生不同的反应途径。对于酯取代的二酮哌嗪，酯基对自由基环化的反应结果和立体化学有重大影响。
• Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
  申请人：Chapal Nicolas

  公开号：US20060223884A1

  公开（公告）日：2006-10-05

  The invention relates to 4-hydroxyisoleucine, isomers, analogs, lactones, salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. More particularly, the invention relates to the use of those compounds in the prevention and treatment of obesity and related syndromes.

  本发明涉及4-羟基异亮氨酸、其同分异构体、类似物、内酯、盐和前药，以及它们的制备过程，以及包含它们的药物组合物。更具体地说，本发明涉及这些化合物在预防和治疗肥胖及相关综合症中的用途。
• Analogs of 4-hydroxyisoleucine and uses thereof
  申请人：Mioskowski Charles

  公开号：US20060199853A1

  公开（公告）日：2006-09-07

  The invention relates to analogs of 4-hydroxyisoleucine, and to lactones, pharmaceutically acceptable salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. The analogs of the invention stimulate both glucose uptake and insulin secretion, and may thus be useful for the prevention and treatment of disorders of carbohydrate or lipid metabolism, including diabetes mellitus (type 1 and type 2 diabetes), pre-diabetes, and Metabolic Syndrome.

  本发明涉及4-羟基异亮氨酸的类似物，以及它们的内酯、药物可接受的盐和前药，其制备过程，以及包含它们的药物组合物。发明的这些类似物能够刺激葡萄糖摄取和胰岛素分泌，因此可用于预防治疗碳水化合物或脂质代谢紊乱，包括糖尿病（1型和2型糖尿病）、前驱糖尿病和代谢综合征。
• A systematic approach to diverse, lead-like scaffolds from α,α-disubstituted amino acids
  作者：Daniel J. Foley、Richard G. Doveston、Ian Churcher、Adam Nelson、Stephen P. Marsden

  DOI：10.1039/c5cc03002a

  日期：——

  A strategy for the efficient lead-oriented synthesis of novel molecular scaffolds is demonstrated. Twenty two scaffolds were prepared from four quaternary α-amino acid building blocks in only 49 synthetic operations, using six connective reactions. The ability of each scaffold to specifically target leadlike chemical space was demonstrated computationally.

  展示了一种高效的以铅为导向的新型分子支架合成策略。仅通过49次合成操作，使用六种连接反应，从四种季铵α-氨基酸构建单元制备了二十二种支架。通过计算展示了每种支架特异地瞄准铅样化学空间的能力。
• Divergent Total Synthesis of the Tricyclic Marine Alkaloids Lepadiformine, Fasicularin, and Isomers of Polycitorols by Reagent-Controlled Diastereoselective Reductive Amination
  作者：Jinkyung In、Seokwoo Lee、Yongseok Kwon、Sanghee Kim

  DOI：10.1002/chem.201404316

  日期：2014.12.22

  We describe a flexible and divergent route to the pyrrolo‐/pyrido[1,2‐j]quinoline frameworks of tricyclic marine alkaloids via a common intermediate formed by the ester–enolate Claisen rearrangement of a cyclic amino acid allylic ester. We have synthesized the proposed structure of polycitorols and demonstrated that the structure of these alkaloids requires revision. In addition to asymmetric formal

  我们描述了通过环氨基酸烯丙基酯的酯-烯酸酯克莱森重排形成的常见中间体，向三环海洋生物碱的吡咯并//吡啶并[1,2- j ]喹啉骨架形成灵活多样的途径。我们已经合成了所提出的聚瓜酚的结构，并证明这些生物碱的结构需要修改。除了不对称的形式合成外，（-）-lepadiformine和（-）-fasicularin的立体选择性和简洁的总合成也可以通过简单的，可商购的起始原料以完全受底物控制的方式完成。这些总合成过程中的关键步骤是常见中间体的依赖试剂的立体选择性还原胺化反应，以产生吲哚并立定55 a或55b的。受阻C-10基团与同烯丙基基团的Aziridinium介导的碳同源性促进了合成。