(5R,6R,9S)-6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide | 929695-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R,6R,9S)-6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide
• CAS: 929695-59-0
• 化学式: C₁₃H₂₂N₂O₂
• 分子量: 238.33
• InChiKey: GYGJMCPUOGIUAN-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5R,6R,9S)-6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide 、 顺式-1,2-二羟甲基乙烯 以 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  胰岛素促分泌素（2 S，3 R，4 S）-4-羟基异亮氨酸的类似物：手性硝酮与烯烃的1,3-偶极环加成反应合成

  摘要：

  （2 S，3 R，4 S）-4-羟基异亮氨酸是胡芦巴中的一种胰岛素促分泌剂分子。（2 S，3 R，4 R）-和（2 R，3 S，4 S）-4-羟基异亮氨酸的非天然类似物通过衍生自任一（-- ）-或（+）-薄荷烯成烯烃。经由烯烃的外向接近硝酮的受阻面而获得的环加合物在还原步骤和手性助剂的裂解后，以良好的总收率生成对映体非纯氨基酸。

  DOI：

  10.1016/j.tetasy.2008.04.006

文献信息

• Cycloadditions of Chiral Nitrones to Racemic 3-Substituted Butenes: A Direct Access with Kinetic Resolution to Enantiopure Dihydroxylated Amino Acids
  作者：Jean-Pierre Praly、Kaiss Aouadi、Sébastien Vidal、Moncef Msaddek

  DOI：10.1055/s-2006-951534

  日期：——

  1,3-Dipolar cycloadditions of racemic 3-substituted 1-butenes to nitrones derived from (-)- or (+)-menthone occurred via exo-approach of the alkene onto the nitrone's less hindered face. This process afforded bicyclic spirpheterocycles as epimers, with selectivities ≤ 4:1, depending on the 3-substituent (R) on the alkene. The selectivity appeared to be influenced by hydrogen bonding (R = OH) or the

  外消旋 3-取代的 1-丁烯与衍生自 (-)- 或 (+)-薄荷酮的硝酮的 1,3-偶极环加成反应是通过烯烃在硝酮受阻较小的面上的外向途径发生的。该过程提供双环螺环作为差向异构体，选择性≤ 4:1，取决于烯烃上的 3-取代基 (R)。作为动力学拆分的结果，选择性似乎受到氢键 (R = OH) 或 R 基团的体积 (R = OBz, Br) 的影响。在手性助剂的还原步骤和裂解之后，获得的环加合物以高总产率得到对映纯的二羟基化非天然氨基酸。
• Novel routes to either racemic or enantiopure α-amino-(4-hydroxy-pyrrolidin-3-yl)acetic acid derivatives and biological evaluation of a new promising pharmacological scaffold
  作者：Samy Cecioni、Kaïss Aouadi、Julie Guiard、Sandrine Parrot、Nathalie Strazielle、Sandrine Blondel、Jean-François Ghersi-Egea、Christian Chapelle、Luc Denoroy、Jean-Pierre Praly

  DOI：10.1016/j.ejmech.2015.05.017

  日期：2015.6

  Cycloaddition between (+) or (-)-menthone-derived nitrones and N-benzyl-3-pyrroline afforded enantiopure spiro-fused heterocycles. The reaction occurred enantio- and diastereo-selectively on the less hindered side of the nitrone, the 3-pyrroline N-benzyl group being oriented outwards, thus controlling the configurations of three simultaneously created chiral centers. From either (+) or (-)-menthone, both enantiomeric cycloadducts were synthesized in excellent yield. Removing the chiral auxiliary and the N-benzyl group delivered a series of enantiopure 4-hydroxy-3-glycinyl-pyrrolidine derivatives in 3-5 steps and 36 to 81 overall yields. Using two other achiral nitrones, shorter routes to racemic analogues were developed. Two of the synthesized compounds markedly lowered extracellular glutamate level and modestly interacted with cannabinoid type-1 receptors. As these two neuroactive compounds were devoid of in vitro toxicity and did not cross the blood brain interface, they might represent potential pharmacological agents to target peripheral organs. (C) 2015 Elsevier Masson SAS. All rights reserved.