(R)-2-氧代噻唑烷-4-羧酸甲酯 | 127761-77-7

• 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
• 中文名称: (R)-2-氧代噻唑烷-4-羧酸甲酯
• 英文名称: L-2-oxothiazolidine-4-carboxylic acid methyl ester
• 英文别名: 4-carbomethoxythiazolidin-2-one；methyl (R)-2-oxothiazolidine-4-carboxylate；(R)-methyl 2-oxothiazolidine-4-carboxylate；methyl (4R)-2-oxo-1,3-thiazolidine-4-carboxylate
• CAS: 127761-77-7
• 化学式: C₅H₇NO₃S
• 分子量: 161.181
• InChiKey: CRXIPBHVCVSPLR-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-氧代噻唑烷-4-羧酸甲酯 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 丙半胱氨酸
  参考文献：
  名称：

  Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer

  摘要：

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.

  DOI：

  10.1021/jo00046a008
• 作为产物：
  描述：

  甲醇 、 丙半胱氨酸 以66%的产率得到(R)-2-氧代噻唑烷-4-羧酸甲酯
  参考文献：
  名称：

  A Convenient Synthesis of Chiral Oxazolidin-2-Ones and Thiazolidin-2-Ones and an Improved Preparation of Triphosgene

  摘要：

  Oxazolidin-2-ones and thiazolidin-2-one are conveniently prepared by condensation of L-serine, L-threonine and L-cysteine, respectively with triphosgene. The corresponding methyl esters may be subsequently obtained by quenching the reaction mixture with methanol, without prior need for the isolation of the free acids. An improved procedure for preparation of triphosgene using an internal cooling system is described.

  DOI：

  10.1080/00397919308012605

文献信息

• Visible‐Light‐Mediated Liberation and In Situ Conversion of Fluorophosgene
  作者：Daniel Petzold、Philipp Nitschke、Fabian Brandl、Veronica Scheidler、Bernhard Dick、Ruth M. Gschwind、Burkhard König

  DOI：10.1002/chem.201804603

  日期：2019.1.2

  to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge‐transfer complex‐dimer as the catalytic active species. Fluorophosgene

  报道了不基于自由基反应性的光催化产生高度亲电中间体的第一个实例。有机光敏剂对稳定的和市售的4-（三氟甲氧基）苄腈进行单电子还原会导致其分裂为氟光气和苄腈。原位产生的氟光气用于通过分子内环化反应以中等至极好的收率制备碳酸盐，氨基甲酸酯和尿素衍生物。瞬态光谱研究表明，形成了一种催化剂电荷转移复合物-二聚体，作为催化活性物质。氟光气作为高反应性中间体，通过NMR间接检测到它的下一个下游碳酰氟中间体。此外，
• Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
  作者：Victor Adebomi、Mahesh Sriram、Xavier Streety、Monika Raj

  DOI：10.1021/acs.orglett.1c01622

  日期：2021.8.20

  secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C–N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation

  在这里，我们解决了仲酰胺位点选择性修饰的长期挑战，并提出了一种简单的两步、无金属方法来选择性地修饰含有多个伯酰胺和仲酰胺的分子中的特定仲酰胺。密度泛函理论 (DFT) 提供了对 C-N 键激活的深入了解。这项研究涵盖了肽后期修饰的独特化学进展，从而利用酰胺将各种官能团结合到天然和合成分子中。
• Carbon Dioxide as a Carbonylating Agent in the Synthesis of 2-Oxazolidinones, 2-Oxazinones, and Cyclic Ureas: Scope and Limitations
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo100268n

  日期：2010.5.7

  Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such

  在2-恶唑烷酮，2-恶嗪酮和环状脲的合成中，二氧化碳可用作方便的羰基化剂。通过在碱性介质中处理伯胺或仲胺基团而生成的瞬态氨基甲酸酯阴离子可以用磷酸化剂（如二苯基磷酰叠氮化物（DPPA）和二苯基氯代磷酸酯（DPPC1））活化，也可以用其他类型的亲电试剂（如SOCl 2，TsCl或氯化铝。羟基将活化的氨基甲酸酯分子内捕获导致形成2-恶唑烷酮或2-恶嗪酮，产率高至优异。该方法已成功地用于从相应的二胺合成高达7元环的环状脲。
• Simple and Efficient N-Acylation Reactions of Chiral Oxazolidine Auxiliaries
  作者：David J. Ager、David R. Allen、David R. Schaad

  DOI：10.1055/s-1996-4402

  日期：1996.11

  A simplified procedure for the N-acylation of oxazolidin-2-one chiral auxiliaries has been developed. The acylations occur at room temperature in the presence of triethylamine and catalytic quantities of 4-(N,N-dimethylamino)pyridine, thereby eliminating the necessity for a strong base such as butyllithium. Acylations with both symmetrical and mixed anhydrides, as well as acid chlorides, occur with a wide variety of oxazolidinone auxiliaries.

  已经开发了一种简化的程序用于N-酰化氧杂环丁烷-2-酮手性辅助剂。酰化在室温下进行，使用三乙胺和催化量的4-(N,N-二甲氨基)吡啶，从而消除了使用强碱（如丁基锂）的必要性。对对称和混合酸酐以及酸氯化物的酰化可以适用于多种氧杂环丁烷酮辅助剂。
• Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
  作者：Hiroyuki Okabe、Asuka Naraoka、Takahiro Isogawa、Shunsuke Oishi、Hiroshi Naka

  DOI：10.1021/acs.orglett.9b01657

  日期：2019.6.21

  dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired

  通过使用二氯乙腈作为水受体，在温和的水性条件下钯催化的伯酰胺脱水有效地进行为腈。设计该转移脱水催化的关键是确定一种有效的水受体二氯乙腈，该水受体在Pd催化剂的帮助下优先于酰胺而不是其他极性官能团反应，并使所需的反应体系趋于能动，从而驱动脱水。