2-甲基-2-丙基{[(5S)-2-氧代-1,3-恶唑烷-5-基]甲基}氨基甲酸酯 | 274264-59-4

• 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: 2-甲基-2-丙基{[(5S)-2-氧代-1,3-恶唑烷-5-基]甲基}氨基甲酸酯
• 英文名称: (5S)-5-tert-butoxycarbonylaminomethyl-1,3-oxazolidin-2-one
• 英文别名: (S)-5-t-Butoxycarbonylaminomethyl-2-Oxazolidinone；(S)-tert-Butyl ((2-oxooxazolidin-5-yl)methyl)carbamate；tert-butyl N-[[(5S)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate
• CAS: 274264-59-4
• 化学式: C₉H₁₆N₂O₄
• 分子量: 216.237
• InChiKey: KBBLJDDYBLDMOU-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基{[(5S)-2-氧代-1,3-恶唑烷-5-基]甲基}氨基甲酸酯 、 氯甲酸苄酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以76%的产率得到(5R)-5-tert-butoxycarbonylaminomethyl-3-benzyloxycarbonyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure (+)- and (−)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

  摘要：

  The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.006
• 作为产物：
  描述：

  (1'S,5R)-5-tert-butoxycarbonylaminomethyl-3-(1'-phenylethyl)-1,3-oxazolidin-2-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以84%的产率得到2-甲基-2-丙基{[(5S)-2-氧代-1,3-恶唑烷-5-基]甲基}氨基甲酸酯
  参考文献：
  名称：

  Synthesis of enantiomerically pure (+)- and (−)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

  摘要：

  The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.006

文献信息

• OXAZOLIDINONE ANTIBIOTIC DERIVATIVES
  申请人：Gude Markus

  公开号：US20100137290A1

  公开（公告）日：2010-06-03

  The invention relates to antibacterial compounds of formula I wherein R 1 is hydrogen, halogen, hydroxy, alkoxy or cyano; Y 1 and Y 2 each represent CH, one or two of U, V, W and X represent(s) N and the remaining each represent CH or, in the case of X, may also represent CR a , R a being halogen, and, in the case of W, may also represent CR b , or each of U, V, W, X, Y 1 and Y 2 represents CH, or each of U, V, W, X and Y 1 represents CH and Y 2 represents N, or also one or, provided R 1 is hydrogen, two of U, V, W, X, Y 1 and Y 2 represent(s) CRC and the remaining each represent CH, R b being alkoxy, alkoxycarbonyl or alkoxyalkoxy and R c being, each time it occurs, independently represents hydroxy or alkoxy; A-B-D represents a chain of 4 to 6 atoms, which 4 to 6 atoms are seleted from carbon, oxygen and nitrogen and may be substituted; E is one of the following groups: in which Z is CH or N and Q is O or S, or E is a phenyl group which is substituted once or twice in the meta and/or para position(s); and to salts of such compounds.

  本发明涉及式I的抗菌化合物，其中R1为氢、卤素、羟基、烷氧基或氰基；Y1和Y2各自代表CH，一个或两个U、V、W和X代表N，其余各自代表CH，或者在X的情况下，也可以代表CRa，其中Ra为卤素，并且在W的情况下，也可以代表CRb，或者U、V、W、X、Y1和Y2各自代表CH，或者U、V、W、X和Y1各自代表CH，而Y2代表N，或者，如果R1为氢，则一个或两个U、V、W、X、Y1和Y2代表CRC，其余各自代表CH，其中Rb为烷氧基、烷氧羰基或烷氧基烷氧基，Rc每次出现时独立地代表羟基或烷氧基；A-B-D代表4至6个原子的链，这4至6个原子选自碳、氧和氮，并且可以被取代；E是以下组之一：其中Z为CH或N，Q为O或S，或者E为苯基，该苯基在间位和/或对位被取代一次或两次；以及这类化合物的盐。
• Process for preparing optically active oxazolidinone derivative
  申请人：Takasago International Corporation

  公开号：US06403804B1

  公开（公告）日：2002-06-11

  Disclosed is a process for preparing an optically active oxazolidinone derivative comprising allowing hydrazine to react on an optically active ester having a hydroxyl group at the 3-position which is represented by formula (II): wherein R1 represents a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, a methoxymethyl group, a benzyloxymethyl group, a benzyloxycarbonylaminomethyl group which may have a substituent or substituents on the benzene ring thereof, an acylaminomethyl group having 3 to 10 carbon atoms, or an alkyloxycarbonylaminomethyl group having 3 to 6 carbon atoms; R2 and R3, which may be the same or different, each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, an acetylaminomethyl group, a benzoylaminomethyl group, or a benzyl group; and * indicates an asymmetric carbon atom, and subjecting the resulting hydrazide to Curtius rearrangement.

  本发明公开了一种制备光学活性噁唑烷酮衍生物的方法，包括让肼在式（II）所代表的在3位具有羟基的光学活性酯上反应，其中R1代表具有1至4个碳原子的低级烷基、苯基、甲氧甲基、苄氧甲基、苄氧羰基氨甲基基团，该基团上的苯环可能具有取代基，或者具有3至10个碳原子的酰氨基甲基基团或3至6个碳原子的烷氧羰基氨甲基基团；R2和R3，可以相同也可以不同，每个代表氢原子、具有1至4个碳原子的低级烷基、苯基、乙酰氨基甲基基团、苯甲酰氨基甲基基团或苄基；*表示不对称碳原子，并将得到的肼酰肼经过Curtius重排反应。
• Process for preparing optically active oxazolidinone derivatives
  申请人：Takasago International Corporation

  公开号：EP1008590B1

  公开（公告）日：2006-10-11
• US6403804B1
  申请人：——

  公开号：US6403804B1

  公开（公告）日：2002-06-11
• US8114867B2
  申请人：——

  公开号：US8114867B2

  公开（公告）日：2012-02-14