(4R)-N-乙酰基)-4-苯基-2-唑烷酮 | 184363-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (4R)-N-乙酰基)-4-苯基-2-唑烷酮
• 中文别名: (4R)-n-乙酰基)-4-苄基-2-噁唑烷酮
• 英文名称: (R)-3-acetyl-4-benzyloxazolidin-2-one
• 英文别名: (4R)-3-acetyl-4-benzyl-1,3-oxazolidin-2-one
• CAS: 184363-65-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: YMVGXIZVSPMNPD-LLVKDONJSA-N

物化性质

• 熔点：
  104 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 储存条件：
  存放于阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  (4R)-N-乙酰基)-4-苯基-2-唑烷酮 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Chiral pyrrolidine derivatives, and methods for preparing compounds thereof

  摘要：

  本发明涉及手性吡咯烷衍生物，以及制备其化合物的方法。本发明的手性吡咯烷衍生物可用作制药和农业化学品的中间体。

  公开号：

  US20060025468A1
• 作为产物：
  描述：

  D-苯丙氨醇 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (4R)-N-乙酰基)-4-苯基-2-唑烷酮
  参考文献：
  名称：

  The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1

  摘要：

  The rationale for targeting the human di-/tripeptide transporter hPEPT1 for oral drug delivery has been well established by several drug and prodrug cases. The aim of this study was to synthesize novel ketomethylene modified tripeptidomimetics and to investigate their binding affinity for hPEPT1. Three related tripeptidomimetics of the structure H-Phe-psi[COCH2]-Ser(Bz)-X-aa-OH were synthesized applying the tandem chain extension aldol reaction, where amino acid derived beta-keto imides were stereoselectively converted to alpha-substituted gamma-keto imides. In addition, three corresponding tripeptides, composed of amide bonds, were synthesized for comparison of binding affinities. The six investigated compounds were all defined as high affinity ligands (K-i-values < 0.5 mM) for hPEPT1 by measuring the concentration dependent inhibition of apical [C-14]Gly-Sar uptake in Caco-2 cells. Consequently, the ketomethylene replacement for the natural amide bond and alpha-side chain modifications appears to offer a promising strategy to modify tripeptidic structures while maintaining a high affinity for hPEPT1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.108

文献信息

• Acyl Transfer Catalysis with 1,2,4-Triazole Anion
  作者：Xing Yang、Vladimir B. Birman

  DOI：10.1021/ol900098q

  日期：2009.4.2

  1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

  1,2,4-三唑阴离子已被确定为一种活性酰基转移催化剂，适用于酯的氨解和酯交换。
• Synthesis and evaluation of N-aryl pyrrolidinones as novel anti-HIV-1 agents. Part 1
  作者：Baogen Wu、Kelli Kuhen、Truc Ngoc Nguyen、David Ellis、Beth Anaclerio、Xiaohui He、Kunyong Yang、Donald Karanewsky、Hong Yin、Karen Wolff、Kimberly Bieza、Jeremy Caldwell、Yun He

  DOI：10.1016/j.bmcl.2006.04.012

  日期：2006.7

  The synthesis and preliminary structure-activity relationship of a series of pyrrolidinones are described. These pyrrolidinones have been characterized as novel non-nucleoside reverse transcriptase inhibitors (NNRTIs) which are highly potent against wild-type and drug-resistant human immunodeficiency viruses (HIV-1).

  描述了一系列吡咯烷酮的合成和初步的构效关系。这些吡咯烷酮已被表征为新型的非核苷类逆转录酶抑制剂（NNRTIs），对野生型和耐药性人免疫缺陷病毒（HIV-1）具有很高的效力。
• BENZOIMIDAZOL-1,2-YL AMIDES AS Kv7 CHANNEL ACTIVATORS
  申请人：Knopp Biosciences LLC

  公开号：US20160075663A1

  公开（公告）日：2016-03-17

  Optionally substituted benzoimidazol-1,2-yl amides, such as compounds of Formula 1 or Formula 2, can be used to treat disorders associated with a Kv7 potassium channel activator. Compositions, medicaments, and dosage forms related to the treatment are also disclosed herein.

  可选择替代的苯并咪唑-1,2-基酰胺，如式1或式2的化合物，可用于治疗与Kv7钾通道激活剂相关的疾病。本文还公开了与治疗相关的组合物、药物和剂型。
• Enantioselective Multicomponent Synthesis of Fused 6-5 Bicyclic 2-Butenolides by a Cascade Heterobicyclisation Process
  作者：Marcos G. Suero、Raquel De la Campa、Laura Torre-Fernández、Santiago García-Granda、Josefa Flórez

  DOI：10.1002/chem.201102288

  日期：2012.6.4

  heterobicyclisation products is the result of the regioselective integration of the Grignard reagent as a propargyl fragment followed by a cascade CO/alkyne/CO insertion, ketene trapping and elimination sequence. By using lithium enolates of chiral N‐acetyl‐2‐oxazolidinones and the corresponding propargylic organocerium reagents, both enantiomers of these bicyclic heterocycles were efficiently prepared with

  铬的烷氧基（芳基/杂芳基）卡宾络合物与酮或酰亚胺烯醇锂的连续偶联，然后与3-取代的（H，TMS，PhCH 2，PhCH 2 CH 2，Me）炔丙基有机镁试剂偶联具有三个模块化点的新型羟基取代双环[4.3.0]-γ-亚烷基-2-丁烯内酯，可有效引入分子复杂性，包括均丙醇核心。这些五或六组分异双环化产物的选择性形成是格氏试剂作为炔丙基片段进行区域选择性整合，随后是级联的CO /炔烃/ CO插入，乙烯酮捕获和消除序列的结果。通过使用手性N的烯醇锂对乙酰基-2-恶唑烷酮和相应的炔丙基有机铈试剂，均以非常高的对映体纯度有效地制备了这些双环杂环的对映体。在结构上，这些稠合的双环丁烯内酯的特征是高度不饱和和氧化的核，并且它们在溶液中显示出很强的蓝色荧光。
• Stereoselective Synthesis of Functionalized <i>trans</i>-2,5-Disubstituted Tetrahydrofurans
  作者：Ronaldo A. Pilli、Valéria B. Riatto、Ivo Vencato

  DOI：10.1021/ol991194u

  日期：2000.1.1

  derived from (S)-glutamic acid, afforded trans- and cis-2,5-disubstituted tetrahydrofurans (trans/cis ratio: R = H, 2:1; R = Me, 8:1; R = Br, 10:1) after desilylation with aqueous HF/CH3CN. Chromatographic separation and LiBH4 reduction allowed the efficient preparation of the corresponding trans-2,5-disubstituted tetrahydrofuran diols and the recovery of the chiral auxiliary.

  [反应：请参见文本]将N-乙酰基，N-丙酰基和N-溴乙酰基（R）-恶唑烷-2-酮的烯醇钛添加到衍生自（S）-谷氨酸的γ-乳糖醇2中，用HF / CH3CN水溶液进行甲硅烷基化后，反式和顺式2,5-二取代的四氢呋喃（反式/顺式比：R = H，2：1； R = Me，8：1； R = Br，10：1）。色谱分离和LiBH4还原可以有效制备相应的反式2,5-二取代四氢呋喃二醇，并可以回收手性助剂。