(2R,5R)-5-(4-bromo-2-butenyl)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one | 862410-59-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5R)-5-(4-bromo-2-butenyl)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one
• 英文别名: (3R,7aR)-7a-[(Z)-4-bromobut-2-enyl]-3-(trichloromethyl)-3,5,6,7-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-one
• CAS: 862410-59-1
• 化学式: C₁₁H₁₃BrCl₃NO₂
• 分子量: 377.493
• InChiKey: SNNIDOBQZGLNAW-WJNJLFNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-(4-bromo-2-butenyl)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 26.0h， 生成 (5S)-7-methyl-1,7-diaza-spiro[4.6]undecane
  参考文献：
  名称：

  Synthesis of enantiopure 5.7-spirodiamines: (S)-1,7-diaza[4.6]undecane and related compounds

  摘要：

  The efficient synthesis of enantiomerically pure (S)-1,7-diaza[4.6]undecane and (S)-7-methyl-1,7-diaza[4.6]undecane and related compounds is reported. These novel diamines are obtained from (S)-proline, which is reacted with chloral to give an enantiomerically pure oxazolidinone, which is alkylated at the alpha-position using cis-1,4-clibromobutene. The resulting allylbromide is then reacted with ammonia or methylamine to yield, as intermediates, allylamines, which ring close to give the corresponding spirolactams. The parent and the 7-methyl (S)-5.7-spirodiamines are obtained via reduction in two steps of the spirolactams. The expected absolute configuration was confirmed by X-ray structural analysis. Enantiomeric excess (> 99.8% ee) was determined using the Mosher amides of the spirodiamines and gas chromatography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.030
• 作为产物：
  描述：

  (2Z)-1,4-二溴-2-丁烯 、 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.08h， 以55%的产率得到(2R,5R)-5-(4-bromo-2-butenyl)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one
  参考文献：
  名称：

  Synthesis of enantiopure 5.7-spirodiamines: (S)-1,7-diaza[4.6]undecane and related compounds

  摘要：

  The efficient synthesis of enantiomerically pure (S)-1,7-diaza[4.6]undecane and (S)-7-methyl-1,7-diaza[4.6]undecane and related compounds is reported. These novel diamines are obtained from (S)-proline, which is reacted with chloral to give an enantiomerically pure oxazolidinone, which is alkylated at the alpha-position using cis-1,4-clibromobutene. The resulting allylbromide is then reacted with ammonia or methylamine to yield, as intermediates, allylamines, which ring close to give the corresponding spirolactams. The parent and the 7-methyl (S)-5.7-spirodiamines are obtained via reduction in two steps of the spirolactams. The expected absolute configuration was confirmed by X-ray structural analysis. Enantiomeric excess (> 99.8% ee) was determined using the Mosher amides of the spirodiamines and gas chromatography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.030

文献信息

• SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF
  申请人：Aptinyx Inc.

  公开号：US20210047324A1

  公开（公告）日：2021-02-18

  Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be useful in the treatment of conditions such as depression and related disorders as well as other disorders.
• [EN] SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS NMDA SPIRO-LACTAMES ET LEURS UTILISATIONS
  申请人：APTINYX INC

  公开号：WO2019152678A1

  公开（公告）日：2019-08-08

  Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be useful in the treatment of conditions such as depression and related disorders as well as other disorders.