3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester | 51814-18-7

• 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: 3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester
• 英文别名: ethyl N-benzoxycarbonyl-3-oxopyrrolidine-2-carboxylate；N-benzyloxycarbonyl-3-ketoproline ethyl ester；1-N-Cbz-3-Oxo-pyrrolidine-2-carboxylic acid ethyl ester；1-O-benzyl 2-O-ethyl 3-oxopyrrolidine-1,2-dicarboxylate
• CAS: 51814-18-7
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: TWMLDSILQXQPCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester 在 palladium on activated charcoal 锂硼氢 、 正丁基锂 、 baker's yeast 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 14.58h， 生成 deacetylslaframine
  参考文献：
  名称：

  Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹

  摘要：

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.

  DOI：

  10.1021/jo9908546
• 作为产物：
  描述：

  2-氮杂丁烷-1,4-二羧酸二乙酯 在 potassium tert-butylate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.5h， 生成 3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester
  参考文献：
  名称：

  Synthesis of 8-epi-castanospermine and 6,7,8-tri-epi-castanospermine

  摘要：

  从羟基脯氨酸前体13选择性地通过酶法合成了8-epi-Castanospermine (11)和6,7,8-三epi- Castanospermine（12）。关键词：Castanospermine，合成，酶法还原，酶法分离，不对称合成。

  DOI：

  10.1139/v00-043

文献信息

• Amino acids as precursors to indolizidine alkaloids
  作者：Mukund P. Sibi、James W. Christensen

  DOI：10.1016/s0040-4039(00)97933-4

  日期：1990.1

  Enantiocontrolled synthesis of indolizidine alkaloids δ-coniceine [(−)-(R)-octahydroindolizine] and (+)-(1S, 8aS)-1-hydroxyindolizidine, the biosynthetic precursor of slaframine, have been achieved through a condensation of L-prolinal and 3R,2S-hydroxyprolinal, respectively, with a 3-carbon synthon.

  吲哚并立生物碱δ-可卡因[（-）-（R）-八氢吲哚并嗪和slaframine的生物合成前体（+）-（1S，8aS）-1-羟基吲哚并嗪]的对映体控制合成通过L-脯氨酸的缩合反应实现和3R，2S-羟基脯氨醛，分别带有3-碳合成子。
• MODIDIFED iRNA AGENTS
  申请人：Alnylam Pharmaceuticals, Inc.

  公开号：US20140316124A1

  公开（公告）日：2014-10-23

  The invention relates to iRNA agents, which preferably include a monomer in which the ribose moiety has been replaced by a moiety other than ribose. The inclusion of such a monomer can allow for modulation of a property of the iRNA agent into which it is incorporated, e.g., by using the non-ribose moiety as a point to which a ligand or other entity, e.g., a lipophilic moiety. e.g., cholesterol, is directly, or indirectly, tethered. The invention also relates to methods of making and using such modified iRNA agents.

  本发明涉及iRNA代理，其中最好包括一个单体，其中核糖基团已被替换为除核糖以外的基团。包括这样的单体可以允许调节iRNA代理的性质，例如，通过使用非核糖基团作为配体或其他实体（例如，亲脂性基团，例如胆固醇）的连接点来实现。本发明还涉及制备和使用这样修改的iRNA代理的方法。
• MODIFIED iRNA AGENTS
  申请人：Alnylam Pharmaceuticals, Inc.

  公开号：US20160264968A1

  公开（公告）日：2016-09-15

  The invention relates to iRNA agents, which preferably include a monomer in which the ribose moiety has been replaced by a moiety other than ribose. The inclusion of such a monomer can allow for modulation of a property of the iRNA agent into which it is incorporated, e.g., by using the non-ribose moiety as a point to which a ligand or other entity, e.g., a lipophilic moiety. e.g., cholesterol, is directly, or indirectly, tethered. The invention also relates to methods of making and using such modified iRNA agents.

  本发明涉及iRNA代理，其中最好包括一个单体，其中核糖基团已被除核糖外的其他基团所替代。包括这样一个单体可以允许调节所含iRNA代理的性质，例如，通过使用非核糖基团作为配体或其他实体（例如，亲脂性基团，例如胆固醇）的点来直接或间接地连接。本发明还涉及制备和使用这种改性iRNA代理的方法。
• Modified iRNA agents
  申请人：Alnylam Pharmaceuticals, Inc.

  公开号：US10676740B2

  公开（公告）日：2020-06-09

  The invention relates to iRNA agents, which preferably include a monomer in which the ribose moiety has been replaced by a moiety other than ribose. The inclusion of such a monomer can allow for modulation of a property of the iRNA agent into which it is incorporated, e.g., by using the non-ribose moiety as a point to which a ligand or other entity, e.g., a lipophilic moiety. e.g., cholesterol, is is directly, or indirectly, tethered. The invention also relates to methods of making and using such modified iRNA agents.

  本发明涉及 iRNA 制剂，它最好包括一种单体，其中的核糖分子已被核糖以外的分子所取代。 加入这种单体可以调节加入其中的 iRNA 制剂的性质，例如，通过使用非核糖分子作为配体或其他实体（如亲脂分子，如胆固醇）直接或间接的连接点。 本发明还涉及制造和使用这种改性 iRNA 制剂的方法。
• 6,7-Dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidines and their derivatives as novel corticotropin-releasing factor 1 receptor antagonists
  作者：Tetsuji Saito、Tetsuo Obitsu、Takashi Kondo、Toshiaki Matsui、Yuuki Nagao、Kensuke Kusumi、Naoya Matsumura、Sonoko Ueno、Akihiro Kishi、Seishi Katsumata、Yoshifumi Kagamiishi、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2011.07.055

  日期：2011.9

  To identify an orally active corticotropin-releasing factor 1 receptor antagonist, a series of 6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidines and their derivatives were designed, synthesized and evaluated. An in vitro study followed by in vivo and pharmacokinetic studies of these heterotricyclic compounds led us to the discovery of an orally active CRF1 receptor antagonist. The results of a structure-activity relationship study are presented. (C) 2011 Elsevier Ltd. All rights reserved.