methyl hydrogen (-)-(1R,2S)-cyclobutane-1,2-dicarboxylate | 88335-88-0

• 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: methyl hydrogen (-)-(1R,2S)-cyclobutane-1,2-dicarboxylate
• 英文别名: (-)-(1R,2S)-2-(methoxycarbonyl)cyclobutanecarboxylic acid；methyl hydrogen (-)-(1R,2S)-cyclobutanedicarboxylate；1-methyl hydrogen (1R,2S)-1,2-cyclobutanedicarboxylate；1-methyl 2-hydrogen (1R,2S)-cyclobutane-1,2-dicarboxylate；(1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid；(1S,2R)-2-(methoxycarbonyl)cyclobutanecarboxylic acid；cyclobutane-1,2-dicarboxylic acid monomethyl ester；rel-(1R,2S)-2-(methoxycarbonyl)cyclobutane-1-carboxylic acid；(1S,2R)-2-methoxycarbonylcyclobutane-1-carboxylic acid
• CAS: 88335-88-0
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: DLSMGFKPSMYVFW-CRCLSJGQSA-N

物化性质

• 沸点：
  85 °C(Press: 0.15 Torr)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl hydrogen (-)-(1R,2S)-cyclobutane-1,2-dicarboxylate 在 palladium on activated charcoal 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 50.0 ℃ 、202.65 kPa 条件下， 反应 6.5h， 生成 甲基(1R,2S)-2-氨基环丁烷羧酸酯
  参考文献：
  名称：

  Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide

  摘要：

  Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane beta -amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded beta -amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-beta -amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00297-4
• 作为产物：
  描述：

  顺式-环丁烷-1,2-二羧酸 在 乙酸酐 、 奎宁 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 60.0h， 生成 methyl hydrogen (-)-(1R,2S)-cyclobutane-1,2-dicarboxylate
  参考文献：
  名称：

  金鸡纳生物碱介导的环状介孔酸酐的实用且高度对映选择性的开环。

  摘要：

  描述了在甲醇存在下金鸡纳生物碱介导的前手性环酐的打开，导致旋光性半酯。结构非常不同的酸酐被转化为其相应的甲基单酯，通过使用奎宁或奎尼丁作为直接添加剂，可以以高达99％ee的形式获得任何一种对映体。反应后，几乎可以定量回收生物碱并重新使用，而不会损失对映选择性。另外，提出了一种催化方案，该方案允许在容易获得的五甲基哌啶（哌啶）存在下亚化学计量使用奎尼丁。

  DOI：

  10.1021/jo000638t

文献信息

• [EN] NOVEL HEPATITIS C VIRUS INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：MEDIVIR AB

  公开号：WO2013095275A1

  公开（公告）日：2013-06-27

  The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

  本发明提供了式(I)的化合物：其中环A和A'独立地是5个成员的可选取代的芳香杂环；Q是C(=O)NR1R1'或式U是C(R4)2，O，S，S(=O)2，C(R4)2C(R4)2，CH2O，O ，CH2S，S ， (=O)2，S(=O)CH2或C=C(Ru)2；X是 ，CHR12，CR12R12，O，S，S(=O)2或NRx；m是0，1，2或3；n是0，1，2或3；其他变量如权利要求中所定义，用于治疗或预防丙型肝炎病毒感染，以及相关方面。
• [EN] BRIDGED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS PONTÉS POUR LE TRAITEMENT DES INFECTIONS BACTÉRIENNES
  申请人：MERCK SHARP & DOHME

  公开号：WO2016123146A1

  公开（公告）日：2016-08-04

  Novel bridged compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.

  本文披露了新型的桥接化合物，以及它们的药用盐、水合物和前药。还披露了包含这些化合物的组合物，制备这些化合物的方法以及将这些化合物用作抗菌剂的方法。所披露的化合物、其药用盐、水合物和前药，以及包含这些化合物、盐、水合物和前药的组合物，对治疗细菌感染及相关疾病和症状是有用的。
• (+)- and (−)-2-Aminocyclobutane-1-carboxylic Acids and Their Incorporation into Highly Rigid β-Peptides:  Stereoselective Synthesis and a Structural Study
  作者：Sandra Izquierdo、Federico Rúa、Abdelouahid Sbai、Teodor Parella、Ángel Álvarez-Larena、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1021/jo0510843

  日期：2005.9.1

  Several derivatives of (+)- and (−)-2-aminocyclobutane-1-carboxylic acid, 1, have been prepared through enantiodivergent synthetic sequences. The stereoselective synthesis of free amino acid (+)-1 has been achieved, and this product has been fully characterized for the first time. Stereocontrolled alternative synthetic methodologies have been developed for the preparation of bis(cyclobutane) β-dipeptides

  通过对映异构的合成序列已经制备了（+）-和（-）-2-氨基环丁烷-1-羧酸1的几种衍生物。立体选择性合成游离氨基酸（+）- 1已实现，并且此产品已首次全面表征。已经开发了立体控制的替代合成方法以高产率制备双（环丁烷）β-二肽。其中，已经合成了对映体和非对映体。还已经制备了由环丁烷残基和线性氨基酸的偶联产生的β，β-和β，δ-二聚体。已经显示出环丁烷环作为单体和二聚体中的结构促进单元的能力。NMR结构研究和DFT理论计算证明了强分子内分子的形成氢键产生顺式[4.2.0]辛烷结构单元，在溶液和气相中均赋予这些分子高刚性。还观察到了由围绕氨基甲酸酯NC（O）键旋转引起的顺式-反式构象平衡的贡献，反式是主要的构象体。在固态中，不存在该平衡，此外，存在分子间氢键。
• A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase
  作者：Peter Mohr、Nada Waespe-?ar?evi?、Christoph Tamm、Krystyna Gawronska、Jacek K. Gawronski

  DOI：10.1002/hlca.19830660815

  日期：1983.12.14

  Pig liver esterase-(PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates. The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10% to 100%. Some of these optically

  猪肝esterase-（PLE）的对称的二羧酸，其中包括二甲基酯的催化水解内消旋-diacids，顺式-1,2-环烷烃酸，并用前手性中心二酸，用14个基板研究。这些立体选择性水解的产物是二元羧酸的手性单酯，对映体过量（ee）为10％至100％。这些光学活性单酯中的一些是天然产物合成中有价值的合成子。
• 2.1.1.5 The spatial distribution of earthquake foci
  作者：G. Schneider

  DOI：10.1007/10201917_18

  日期：——

  This document is part of Subvolume A of Volume 2 ‘Geophysics of the Solid Earth, the Moon and the Planets’ of Landolt-Börnstein - Group V Geophysics.

  该文档是《Landolt-Börnstein - V组地球物理学》第2卷《固体地球、月球和行星的地球物理学》子卷A的一部分。