麻黄恶碱 | 16251-46-0

• 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: 麻黄恶碱
• 英文名称: (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one
• 英文别名: (4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-one；3,4-dimethyl-5-phenyl-oxazolidin-2-one；(4S)-3,4r-dimethyl-5c-phenyl-oxazolidin-2-one；(4S)-3,4r-Dimethyl-5c-phenyl-oxazolidin-2-on；(4S,5R)-3,4-dimethyl-5-phenyl-2-oxazolidinone；Ephedroxane
• CAS: 16251-46-0
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: MNYARIILPGRTQL-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  麻黄恶碱 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 DL-甲基苯丙胺
  参考文献：
  名称：

  METHOD FOR MAKING PHARMACEUTICAL COMPOUNDS

  摘要：

  制备B式苯乙胺的方法：其中R2、R3、R4、R5、R6、Rα、Rβ和Rn分别独立地选自氢、烷基、酰基、芳基、酰胺、氨基酸、糖和核苷酸。该方法包括在无碱的情况下还原A式化合物的步骤：其中R2、R3、R4、R5、R6、Rα、Rβ和Rn如上所定义。

  公开号：

  US20100125146A1
• 作为产物：
  描述：

  N-(mercaptothiocarbonyl)ephedrine 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以61%的产率得到麻黄恶碱
  参考文献：
  名称：

  Moreno-Manas, Marcial; Padros, Imma, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1235 - 1240

  摘要：

  DOI：

文献信息

• Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity
  作者：Claude Agami、François Couty、Louis Hamon、Olivier Venier

  DOI：10.1016/0040-4039(93)88071-p

  日期：1993.7

  Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AM1 calculations.

  用对甲苯磺酰氯处理高手性β-氨基醇的N-叔丁氧基羰基衍生物，得到2-ax唑烷酮。这些杂环是通过中间体甲苯磺酸酯中氨基甲酸酯部分的分子内亲核攻击产生的。N-甲基取代基的存在增强了环化速率，并且通过AM1计算研究了该效应。
• The Reaction of β-Amino Alcohols with 1,1′-Carbonyldiimidazole − Influence of the Nitrogen Substituent on the Reaction Course
  作者：Sara Cutugno、Gianluca Martelli、Lucia Negro、Diego Savoia

  DOI：10.1002/1099-0690(200102)2001:3<517::aid-ejoc517>3.0.co;2-n

  日期：2001.2

  The reaction of β-amino alcohols with 1,1′-carbonyldiimidazole in dichloromethane is affected by the size of the nitrogen substituent. 1,3-Oxazolidin-2-ones are exclusively obtained from N-H, N-methyl and N-arylmethyl derivatives. O-(1-Imidazolyl)carbonyl derivatives are formed as intermediates from N-[1-(2-pyridyl)alkyl]-(S)-valinol and are mainly or exclusively converted into aziridines in the presence

  β-氨基醇与 1,1'-羰基二咪唑在二氯甲烷中的反应受氮取代基大小的影响。1,3-Oxazolidin-2-ones 仅从 NH、N-甲基和 N-芳甲基衍生物中获得。O-(1-咪唑基)羰基衍生物作为中间体由 N-[1-(2-吡啶基)烷基]-(S)-缬氨醇形成，主要或仅在水存在下转化为氮丙啶，尽管环化是被三苯甲基等大的 N 取代基阻碍。
• Ramoplanin derivatives possessing antibacterial activity
  申请人：Raju G. Bore

  公开号：US20060211603A1

  公开（公告）日：2006-09-21

  Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

  新型拉莫普兰衍生物已被披露。这些拉莫普兰衍生物表现出抗菌活性。由于本发明的化合物对革兰氏阳性细菌表现出强效活性，它们是有用的抗微生物药剂。该化合物的合成方法和使用方法也已被披露。
• Carbon Dioxide as a Carbonylating Agent in the Synthesis of 2-Oxazolidinones, 2-Oxazinones, and Cyclic Ureas: Scope and Limitations
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo100268n

  日期：2010.5.7

  Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such

  在2-恶唑烷酮，2-恶嗪酮和环状脲的合成中，二氧化碳可用作方便的羰基化剂。通过在碱性介质中处理伯胺或仲胺基团而生成的瞬态氨基甲酸酯阴离子可以用磷酸化剂（如二苯基磷酰叠氮化物（DPPA）和二苯基氯代磷酸酯（DPPC1））活化，也可以用其他类型的亲电试剂（如SOCl 2，TsCl或氯化铝。羟基将活化的氨基甲酸酯分子内捕获导致形成2-恶唑烷酮或2-恶嗪酮，产率高至优异。该方法已成功地用于从相应的二胺合成高达7元环的环状脲。
• Reactivity difference between diphosgene and phosgene in reaction with (2,3-anti)-3-amino-1,2-diols
  作者：A. Hamdach、E.M. El Hadrami、S. Gil、R.J. Zaragozá、E. Zaballos-García、J. Sepúlveda-Arques

  DOI：10.1016/j.tet.2006.04.033

  日期：2006.6

  In reactions of (2,3-anti)-3-amino-1,2-diols with diphosgene and phosgene and their conversion into 1,3-oxazolidin-2-ones, some differences in the stereochemistry of the reactions have been found with these two reagents. The reactions with phosgene afforded the expected cis-oxazolidinones, and in the reaction with diphosgene under the same reaction conditions, the trans-oxazolidinones were also obtained

  在（2,3-抗）-3-氨基-1,2-二醇与双光气和光气的反应以及它们转化为1,3-恶唑烷-2-酮的反应中，已发现反应的立体化学存在一些差异。这两种试剂。与光气的反应提供了预期的顺式-恶唑烷酮，并且在相同的反应条件下与双光气的反应中，还获得了反式-恶唑烷酮。