(6S)-N-1-(tert-butoxycarbonyl)-5-phenyl-6-isopropyl-1,2,3,6-tetrahydro-2-pyrazinone | 281194-62-5

• 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: (6S)-N-1-(tert-butoxycarbonyl)-5-phenyl-6-isopropyl-1,2,3,6-tetrahydro-2-pyrazinone
• 英文别名: tert-butyl (2S)-6-oxo-3-phenyl-2-propan-2-yl-2,5-dihydropyrazine-1-carboxylate
• CAS: 281194-62-5
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: IKIKAJODHVQGGA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S)-N-1-(tert-butoxycarbonyl)-5-phenyl-6-isopropyl-1,2,3,6-tetrahydro-2-pyrazinone 在 potassium carbonate palladium diacetate 、 四丁基溴化铵 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  由具有1,2,3,6-四氢吡嗪-2-一结构的α，β-（Z）-二氢氢化物衍生物不对称合成α-氨基酸

  摘要：

  手性（Ž）-α，β-didehydroamino酸（DDAA）衍生物14，15和16是从所获得的新的手性iminic环状甘氨酸模板与1,2,3,6- tetrahydropyrazin -2-酮结构10通过与羰基缩合化合物，Eschenmoser盐和Bredereck试剂。使用Heck烯化和乙烯基亲核取代，二氢丙氨酸衍生物15和烯胺酮16可以得到DDAA衍生物14。这些DDAA衍生物14和15 进行非对映选择性环丙烷化，1，3-偶极和Diels-Alder环加成反应，水解后得到相应的环状和双环α-氨基酸。

  DOI：

  10.1016/s0040-4020(01)00553-1
• 作为产物：
  描述：

  2-amino-N-[(2S)-3-methyl-1-oxo-1-phenylbutan-2-yl]acetamide 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (6S)-N-1-(tert-butoxycarbonyl)-5-phenyl-6-isopropyl-1,2,3,6-tetrahydro-2-pyrazinone
  参考文献：
  名称：

  Chiral (Z)-α,β-didehydroamino acid derivatives from a new chiral glycine equivalent with a 1,2,3,6-tetrahydropyrazin-2-one structure: applications to the synthesis of 1-aminocyclopropanecarboxylic acids and bicyclic α-amino acids

  摘要：

  The new chiral glycine equivalent 9, easily obtained from(+)-alpha-aminoisovalerophenone and glycine, afforded chiral (Z)-alpha,beta-didehydroamino acid (DDAA) derivatives 13 and 14 with a 1,2,3,6-tetrahydropyrazin-2-one structure. Compounds 13 and 14 were synthesised by reaction of 9 with Eschenmoser's salt and by condensation reactions with aldehydes or acetone under PTC conditions, respectively. The diastereoselective cyclopropanation of 14, followed by hydrolysis, furnished (-)-allo-norcoronamic acid with high ee, whilst diastereoselective Diels-Alder reaction of dienophile 13 and cyclopentadiene afforded, after double bond hydrogenation and hydrolysis, (-)-2-aminonorbornane-2-carboxylic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00023-9

文献信息

• Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetrahydropyrazin-2-one structure
  作者：Tomás Abellán、Balbino Mancheño、Carmen Nájera、José M Sansano

  DOI：10.1016/s0040-4020(01)00553-1

  日期：2001.7

  structure 10 by condensation with carbonyl compounds, Eschenmoser's salt and Bredereck's reagent, respectively. The didehydroalanine derivative 15 and the enaminone 16 can give DDAA derivatives 14 using Heck olefination and vinylic nucleophilic substitution. These DDAA derivatives 14 and 15 undergo diastereoselective cyclopropanation, 1,3-dipolar and Diels–Alder cycloaddition reactions giving, after

  手性（Ž）-α，β-didehydroamino酸（DDAA）衍生物14，15和16是从所获得的新的手性iminic环状甘氨酸模板与1,2,3,6- tetrahydropyrazin -2-酮结构10通过与羰基缩合化合物，Eschenmoser盐和Bredereck试剂。使用Heck烯化和乙烯基亲核取代，二氢丙氨酸衍生物15和烯胺酮16可以得到DDAA衍生物14。这些DDAA衍生物14和15 进行非对映选择性环丙烷化，1，3-偶极和Diels-Alder环加成反应，水解后得到相应的环状和双环α-氨基酸。
• Chiral (Z)-α,β-didehydroamino acid derivatives from a new chiral glycine equivalent with a 1,2,3,6-tetrahydropyrazin-2-one structure: applications to the synthesis of 1-aminocyclopropanecarboxylic acids and bicyclic α-amino acids
  作者：Tomás Abellán、Carmen Nájera、José M Sansano

  DOI：10.1016/s0957-4166(00)00023-9

  日期：2000.3

  The new chiral glycine equivalent 9, easily obtained from(+)-alpha-aminoisovalerophenone and glycine, afforded chiral (Z)-alpha,beta-didehydroamino acid (DDAA) derivatives 13 and 14 with a 1,2,3,6-tetrahydropyrazin-2-one structure. Compounds 13 and 14 were synthesised by reaction of 9 with Eschenmoser's salt and by condensation reactions with aldehydes or acetone under PTC conditions, respectively. The diastereoselective cyclopropanation of 14, followed by hydrolysis, furnished (-)-allo-norcoronamic acid with high ee, whilst diastereoselective Diels-Alder reaction of dienophile 13 and cyclopentadiene afforded, after double bond hydrogenation and hydrolysis, (-)-2-aminonorbornane-2-carboxylic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.