(4R)-3-acetyl-4-isopropyl-2-oxazolidinone | 77887-48-0

• 物质功能分类: 生物化工 - 多肽
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-3-acetyl-4-isopropyl-2-oxazolidinone
• 英文别名: (4R)-3-acetyl-4-propan-2-yl-2-oxazolidinone；(4R)-3-acetyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 77887-48-0
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: DDLQJZMVXVQYJT-ZETCQYMHSA-N

物化性质

• 沸点：
  285.4±9.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (4R)-3-acetyl-4-isopropyl-2-oxazolidinone 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-((4R)-4-isopropyl-2-oxooxazolidin-3-yl)-3-phenylpropane-1,3-dione
  参考文献：
  名称：

  Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles

  摘要：

  埃文斯辅基取代的β-酮亚胺的反极化烷基化反应可获得对映纯度高的产物，收率在40%到80%之间。

  DOI：

  10.1039/c4ob02601b
• 作为产物：
  描述：

  (R)-(+)-4-异丙基-2-恶唑啉酮 、 乙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以79%的产率得到(4R)-3-acetyl-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles

  摘要：

  埃文斯辅基取代的β-酮亚胺的反极化烷基化反应可获得对映纯度高的产物，收率在40%到80%之间。

  DOI：

  10.1039/c4ob02601b

文献信息

• Practical Formal Total Syntheses of the Homocamptothecin Derivative and Anticancer Agent Diflomotecan via Asymmetric Acetate Aldol Additions to Pyridine Ketone Substrates
  作者：René Peters、Martin Althaus、Christian Diolez、Alain Rolland、Eric Manginot、Marc Veyrat

  DOI：10.1021/jo060928v

  日期：2006.9.1

  scalable asymmetric routes to DE ring fragment 7, a key building block in the synthesis of the homocamptothecin derivative diflomotecan 4, are described. The “acetal route” starts from 2-chloro-4-cyanopyridine 8 and represents an enantioselective and optimized modification of the original racemic discovery chemistry synthesis. The inefficient optical resolution procedure was replaced by an efficient asymmetric

  描述了两种实际，有效且可扩展的至DE环片段7的不对称路线，DE环片段7是高喜树碱衍生物双氟醚4合成中的关键组成部分。“缩醛途径”始于2-氯-4-氰基吡啶8，代表对映体选择性和对原始外消旋发现化学合成的优化修饰。低效率的光学拆分程序被高效的不对称乙酸酯醛醇加成剂（dr 87:13）取代到酮基质上，这是生成具有高立体选择性的（R）-构型四元立体中心的关键步骤。7最终，在九个步骤中以8.9％的总收率（er 99.95：0.05）获得了目标产物，从而避免了色谱纯化，并且与初始操作相比具有优势。在从2-氯异烟酸酸41开始的相关“酰胺途径”中，使用仲酰胺指导基团来促进吡啶3-位的邻位锂化。该方案的关键步骤再次包括实际的不对称乙酸羟醛加成（dr = 87:13）。因此，在九个步骤中，仅需进行一次色谱纯化，即可以11.1％的总收率（er> 99.95：0.05）获得DE环结构单元7。
• Sixteen-membered macrolide compounds
  申请人：——

  公开号：US20020111317A1

  公开（公告）日：2002-08-15

  The present invention provides novel sixteen-membered macrolide compounds that are useful as anti-infective agents or as intermediates thereto. The present invention also provides methods for the preparation of these compounds, and methods and formulations for their use. In one aspect of the present invention, sixteen-membered macrolide possessing a side chain Z are provided where Z is aliphatic, aryl, alkylaryl, halide, ═NOR 3 , ═NNHR 3 , or —W—R 3 where W is O, S, NC(═O)R 4 , NC(═O)OR 4 , NC(═O)NHR 4 or NR 4 where R 3 and R 4 are each independently hydrogen, aliphatic, aryl or alkylaryl. In another aspect of the present invention, bicyclic compounds are provided where one of the cyclic-components is a sixteen-membered macrolide and the other is a cyclic moiety whose cyclic structure is formed by between 3 and 10 atoms. In another aspect of the present invention, sixteen-membered macrolide compounds that bind to the domain II region of the 23S RNA are provided.

  本发明提供了新型的十六元大环内酯化合物，可用作抗感染药物或其中间体。本发明还提供了制备这些化合物的方法，以及它们的使用方法和配方。在本发明的一个方面，提供了具有侧链Z的十六元大环内酯，其中Z是脂肪族、芳香族、烷基芳基、卤素、═NOR3、═NNHR3或—W—R3，其中W为O、S、NC(═O)R4、NC(═O)OR4、NC(═O)NHR4或NR4，其中R3和R4各自独立地为氢、脂肪族、芳香族或烷基芳基。在本发明的另一个方面，提供了双环化合物，其中一个环组分是十六元大环内酯，另一个是由3至10个原子形成的环状基团。在本发明的另一个方面，提供了与23S RNA的II区域结合的十六元大环内酯化合物。
• (2S,3S,4R)-4-Amino-3-hydroxy-2-methylpentanoic acid. Enantioselective synthesis of an amino acid constituent of bleomycin.
  作者：Robert M. DiPardo、Mark G. Bock

  DOI：10.1016/s0040-4039(00)94012-7

  日期：1983.1

  (2S,3S,4R)-4-Amino-3-hydroxy-2-methylpentanoic acid has been synthesized through acylation of a chiral enolate and subsequent stereoselective reduction.

  （2S，3S，4R）-4-氨基-3-羟基-2-甲基戊酸是通过手性烯酸酯的酰化反应和随后的立体选择性还原反应合成的。
• Application of Modified Mosher’s Method to<i>α</i>-Aromatic Secondary Alcohols. Exception of the Rule and Conformational Analyses
  作者：Ikuko I. Ohtani、Kaori Hotta、Yoshiyasu Ichikawa、Minoru Isobe

  DOI：10.1246/cl.1995.513

  日期：1995.7

  The modified Mosher’s method was applied to the secondary alcohols possessing an aromatic ring on α-carbon. Some of the alcohols had the irregular Δδ values on β-protons, which were presumably due to the anisotropic effects of α-aromatic groups. In these cases, the absolute configurations were successfully determined by the modified Mosher’s method with elimination of irregular Δδ data.

  将改进的 Mosher 方法应用于在 α-碳上具有芳环的仲醇。一些醇在 β-质子上具有不规则的 Δδ 值，这可能是由于 α-芳族基团的各向异性效应。在这些情况下，通过消除不规则 Δδ 数据的修正 Mosher 方法成功地确定了绝对构型。
• [EN] SIXTEEN-MEMBERED MACROLIDE COMPOUNDS<br/>[FR] COMPOSES MACROLIDES A SEIZE ELEMENTS
  申请人：KOSAN BIOSCIENCES INC

  公开号：WO2002032916A2

  公开（公告）日：2002-04-25

  The present invention provides novel sixteen-membered macrolide compounds that are useful as anti-infective agents or as intermediates thereto. The present invention also provides methods for the preparation of these compounds, and methods and formulations for their use. In one aspect of the present invention, sixteen-membered macrolide possessing a side chain Z are provided where Z is aliphatic, aryl, alkylaryl, halide, =NOR?3, =NNHR3¿, or -W-R3 where W is O, S, NC(=O)R4, NC(=O)OR4, NC(=O)NHR?4 or NR4¿ where R?3 and R4¿ are each independently hydrogen, aliphatic, aryl or alkylaryl. In another aspect of the present invention, bicyclic compounds are provided where one of the cyclic-components is a sixteen-membered macrolide and the other is a cyclic moiety whose cyclic structure is formed by between 3 and 10 atoms. In another aspect of the present invention, sixteen-membered macrolide compounds that bind to the domain II region of the 23S RNA are provided.