(4S,5S)-3H-hexahydrobenzoxazolidin-2-one | 189942-51-6

• 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: (4S,5S)-3H-hexahydrobenzoxazolidin-2-one
• 英文别名: trans-hexahydrobenzoxazolidin-2-one；(3aS,7aS)-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazol-2-one
• CAS: 189942-51-6
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: MZZMFGLUGZUKRI-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-3H-hexahydrobenzoxazolidin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 生成
  参考文献：
  名称：

  Asymmetric Michael addition using N-cinnamoyl- and N-crotonyl-trans-hexahydrobenzoxazolidin-2-ones

  摘要：

  Preparation of N-cinnamoyl- and N-crotonyl-oxazolidin-2-ones 2 and 3 or ent-2 and ent-3 from (4S,5s)- and (4R,5R)trans-hexahydrobenzoxazolidin-2-ones 1 or ent-1 are reported. Stereoselective copper promoted conjugated additions of Grignard reagents to chiral N-enoyl amides 2 and 3 or ent-2 and ent-3 in the presence of Zn(II) salts afforded the 1,4-addition products 4-11 and the corresponding enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.065
• 作为产物：
  描述：

  (1'S)-2-[N-(α-phenylethyl)amino]cyclohexanol 在 氨 、 lithium 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (4S,5S)-3H-hexahydrobenzoxazolidin-2-one
  参考文献：
  名称：

  Preparation of enantiomerically pure cis- and trans-N-(propionyl)hexahydrobenzoxazolidin-2-ones

  摘要：

  A high-yield, five-step synthesis of novel enantiomerically pure cis- and trans-N-(propionyl)-hexahydrobenzoxazolidin-2-ones 5a-d from cyclohexene oxide and (S)-alpha-methylbenzylamine is described. The highly diastereoselective benzylation of 5b is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00064-5

文献信息

• New Options for the Reactivity of the Burgess Reagent with Epoxides in Both Racemic and Chiral Auxiliary Modes - Structural and Mechanistic Revisions, Computational Studies, and Application to Synthesis
  作者：Hannes Leisch、Bradford Sullivan、Branden Fonovic、Travis Dudding、Tomas Hudlicky

  DOI：10.1002/ejoc.200900159

  日期：2009.6

  reagent with epoxides yields diastereomeric pairs of sulfamidates, which lead to cis and trans amino alcohols in each enantiomeric series. Experimental and spectral details are provided for all new sulfamidates and the products derived from them. Structure revisions have been made for several previously reported products from the reactions of the Burgess reagent with cyclic oxiranes and styrene diols.

  Burgess 试剂的手性辅助形式与环氧化物的反应产生氨基磺酸盐的非对映体对，这导致每个对映体系列中的顺式和反式氨基醇。提供了所有新磺胺酯及其衍生产品的实验和光谱细节。Burgess 试剂与环状环氧乙烷和苯乙烯二醇反应的几种先前报道的产物已经进行了结构修正。还建议对伯吉斯试剂与 1,2-二醇和环氧化物反应的可能机制进行相当大的修改。最后，包括对非手性形式的 Burgess 试剂与环氧乙烷相互作用的密度泛函理论 (DFT) 研究，以及对在使用 C2 对称催化剂的催化模式下进行的反应中观察到的缺乏不对称诱导的解释。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Chiral Version of the Burgess Reagent and its Reactions with Epoxides
  作者：Tomas Hudlicky、Hannes Leisch、Rachel Saxon、Bradford Sullivan

  DOI：10.1055/s-2006-932450

  日期：——

  A chiral auxiliary version of the Burgess reagent was prepared, and its reactions with epoxides were studied. Diastereomeric sulfamidates were converted to both enantiomers of protected trans-amino alcohols with ee of 84-98%.

  制备了 Burgess 试剂的手性辅助形式，并研究了它与环氧化物的反应。非对映体磺酰胺被转化为受保护的反式氨基醇的两种对映异构体，ee 为 84-98%。
• A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions
  作者：David E. White、Pamela M. Tadross、Zhe Lu、Eric N. Jacobsen

  DOI：10.1016/j.tet.2014.03.043

  日期：2014.7

  enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen) Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of

  （salen）Co催化剂（4a）可以由廉价的可商购的前体在短的，无色谱的合成中制备为环状低聚物的混合物。相对于各种对映选择性环氧开环反应中的单体和其他多聚（salen）Co催化剂，该催化剂的反应性和对映选择性显着提高。通过用水，酚和伯醇的亲核开环，在末端环氧化物的动力学拆分中说明了催化剂4a的应用。通过添加水和氨基甲酸酯使内消旋环氧化合物不对称化；并通过醇和酚的分子内开环使氧杂环丁烷脱对称。在催化条件下，配合物4a的良好溶解性能促进了机理研究，阐明低聚作用的基础。最后，提供了催化剂选择指南，以针对每种反应类别描述低聚催化剂4a相对于（salen）Co单体1的特定优点。
• OXAZOLIDIN-2-ONE COMPOUNDS AND USES THEREOF
  申请人：Novartis AG

  公开号：US20130225574A1

  公开（公告）日：2013-08-29

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及氧唑烷-2-酮取代嘧啶化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其药物组合物、制备方法和用于治疗依赖于PI3K的疾病、病症和疾病的用途。
• Aluminium-Catalysed Oxazolidinone Synthesis and their Conversion into Functional Non-Symmetrical Ureas
  作者：Victor Laserna、Wusheng Guo、Arjan W. Kleij

  DOI：10.1002/adsc.201500635

  日期：2015.9.14

  range of functional oxazolidinones is reported. The method is based on cheap and readily available starting materials including terminal and internal (bicyclic) epoxides and phenyl carbamate. The oxazolidinones serve as highly useful synthons for the high yield preparation of non‐symmetrical ureas by nucleophilic ring‐opening affording the targeted urea compounds with excellent functional group diversity

  据报道，一种有效且实用的铝催化方法可用于一系列功能性恶唑烷酮。该方法基于便宜且容易获得的起始原料，包括末端和内部（双环）环氧化物和氨基甲酸苯酯。恶唑烷酮类化合物是非常有用的合成子，可通过亲核开环高产率制备非对称脲，为目标脲化合物提供了出色的官能团多样性，高区域选择性和高达> 99％的分离产率。