(2S,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine | 89675-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
• 英文别名: 3,4S-dimethyl-2S,5R-diphenyl-oxazolidine；Oxazolidine, 3,4-dimethyl-2,5-diphenyl-, (2S,4S,5R)-；(2S,4S,5R)-3,4-dimethyl-2,5-diphenyl-1,3-oxazolidine
• CAS: 89675-44-5
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: UYHFNMAZLZQLFT-JQFCIGGWSA-N

物化性质

• 沸点：
  366.9±30.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine 在 磺酰氯 、 柠檬酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 [((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-phenyl-acetonitrile
  参考文献：
  名称：

  Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols

  摘要：

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.092
• 作为产物：
  描述：

  2--2-phenylethanenitrile 100.0 ℃ 、666.61 Pa 条件下， 生成 (2S,4S,5R)-3,4-dimethyl-2,5-diphenyloxazolidine
  参考文献：
  名称：

  Chang, Chih-Jung; Fang, Jim-Min; Lee, Gene-Hsian, Journal of the Chemical Society. Perkin transactions I, 1994, # 24, p. 3587 - 3594

  摘要：

  DOI：

文献信息

• Stability Studies of Oxazolidine-Based Compounds Using 1H NMR Spectroscopy
  作者：Gerard P. Moloney、Magdy N. Iskander、David J. Craik

  DOI：10.1002/jps.22108

  日期：2010.8

  A series of oxazolidine-based compounds with a variety of substituents in positions 2 and 3 was synthesized and their stability studied. Ring opened intermediates formed on addition of limiting amounts of D(2)O to oxazolidine solutions, as observed by NMR. As the hydrolysis reactions proceeded, a series of novel dimeric beta-amino alcohol compounds formed via an internal reaction between ephedrine

  合成了一系列在2和3位具有各种取代基的恶唑烷基化合物，并对其稳定性进行了研究。如通过NMR所观察到的，在向恶唑烷溶液中添加有限量的D（2）O时形成了开环中间体。随着水解反应的进行，麻黄碱与开环中间体之间的内部反应形成了一系列新型的二聚β-氨基醇化合物。含有吸电子硝基取代基的2-苯基取代的恶唑烷化合物比未取代的衍生物和甲氧基取代的化合物水解得更快，硝基取代基似乎可以稳定开环的中间体。两种恶唑烷衍生物，在2位具有甲基和质子 现已发现，它们比2-苯基取代的化合物对恶唑烷水解更稳定。掺入苯基取代基在3位上的恶唑烷，合成并发现是比在位置3结合有甲基取代基稳定的少选择恶唑烷衍生物作为合成中间体时，这些基本结构 - 活性关系可能是有用的，并作为前药为含有递送化合物的β-氨基醇或醛组分。
• Heterogeneous rhodium-catalyzed hydrogenation conditions for the highly effective synthesis of 1,3-oxazolidines from 1,2-amino alcohols and nitriles
  作者：Stéphane Létinois、Jean-Christophe Dumur、Françoise Hénin、Jacques Muzart

  DOI：10.1016/s0040-4039(98)00192-0

  日期：1998.4

  for the synthesis of 1,3-oxazolidines in high yields using 1,2-amino alcohols, nitriles, an atmospheric pressure of hydrogen and catalytic quantites of rhodium on carbon powder is presented. This reaction probably involves the semi-hydrogenation of the nitrile followed by condensation with the amino alcohol. The process may constitute the key step in a two-step sequence for reducing a nitrile into the

  提出了使用1，2-氨基醇，腈，氢气的大气压和铑在碳粉上的催化量来容易地以高产率合成1，3-恶唑烷的方法。该反应可能涉及腈的半氢化，然后与氨基醇缩合。该方法可以按两步顺序构成关键步骤，以将腈还原为相应的醛。
• Stereochemistry-60
  作者：Claude Agami、Toufic Rizk

  DOI：10.1016/s0040-4020(01)96496-8

  日期：1985.1

  controlled oxazolidine formation was observed with aromatic aldehydes substituted by electron-withdrawing groups. The stereoselectivity is solvent dependent: non-stereoselective ring closure occurred in chloroform while a high diastereodifferentiation was observed in methanol. The first oxazolidine showing an unambiguous 2R configuration was synthesized from p-bromobenzaldehyde and (-)-ephedrine in alcohol

  用吸电子基团取代的芳族醛观察到动力学控制的恶唑烷的形成。立体选择性取决于溶剂：在氯仿中发生非立体选择性闭环，而在甲醇中观察到高非对映异构性。由对-溴苯甲醛和（-）-麻黄碱在酒精介质中合成了第一个具有清晰2R构型的恶唑烷。为了阐明立体选择性的差异，提出了一种涉及由醇类溶剂进行亲核辅助的机理。
• Role of solvent on the diastereoselectivity of oxazolidine formation from (–)-ephedrine
  作者：Claude Agami、Toufic Rizk

  DOI：10.1039/c39830001485

  日期：——

  Under kinetic control, the stereochemical course of the condensation between (–)-ephedrine and p-cyano-or p-nitro-benzaldehyde is solvent dependent; no noticeable stereoselectivity was observed in chloroform whereas diastereo-differentiation occurred in methanol.

  在动力学控制下，（-）-麻黄碱与对-氰基-或对-硝基-苯甲醛之间缩合的立体化学过程取决于溶剂。在氯仿中没有观察到明显的立体选择性，而在甲醇中发生了非对映异构。
• Stereochemistry of ephedrine- and pseudo-ephedrine-derived oxazolidines and of their N-borane adducts determined by nuclear Overhauser effect difference spectroscopy
  作者：Fernando Santiesteban、Carlos Grimaldo、Rosalinda Contreras、Bernd Wrackmeyer

  DOI：10.1039/c39830001486

  日期：——

  Nuclear Overhauser effect difference spectra of 1,3-oxazolidines derived from ephedrine and pseudo-ephedrine and of their N-borane adducts allow the configuration at C(2) and N to be assigned.

  源自麻黄碱和伪麻黄碱的1,3-恶唑烷及其N-硼烷加合物的核Overhauser效应差异光谱可指定C（2）和N处的构型。