(3S,6R,7R,7aS)-3-isopropyl-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione | 1569081-49-7

• 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: (3S,6R,7R,7aS)-3-isopropyl-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione
• 英文别名: (1S,2R,6R,9S)-11-anilino-4,4-dimethyl-9-propan-2-yl-3,5-dioxa-8,11-diazatricyclo[6.3.0.02,6]undecane-7,10-dione
• CAS: 1569081-49-7
• 化学式: C₁₈H₂₃N₃O₄
• 分子量: 345.398
• InChiKey: JNPVXTOROQAPGP-XQLPTFJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6R,7R,7aS)-3-isopropyl-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到(3S,6R,7R,7aS)-6,7-dihydroxy-3-isopropyl-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione
  参考文献：
  名称：

  A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones

  摘要：

  The cyclocondensation reactions between L-alpha-amino acid phenylhydrazides and 2,3-O-isopropylidene-L-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, which were converted by acidic hydrolysis with MeOH-HCl into their corresponding optically active (35,6R,7R,7aS)-3-substituted-6,7-dihydroxy-l-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.002
• 作为产物：
  描述：

  苯肼 在 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (3S,6R,7R,7aS)-3-isopropyl-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-dione
  参考文献：
  名称：

  A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones

  摘要：

  The cyclocondensation reactions between L-alpha-amino acid phenylhydrazides and 2,3-O-isopropylidene-L-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, which were converted by acidic hydrolysis with MeOH-HCl into their corresponding optically active (35,6R,7R,7aS)-3-substituted-6,7-dihydroxy-l-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.002

文献信息

• A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones
  作者：Yakdhane Kacem、Béchir Ben Hassine

  DOI：10.1016/j.tetasy.2013.12.002

  日期：2014.2

  The cyclocondensation reactions between L-alpha-amino acid phenylhydrazides and 2,3-O-isopropylidene-L-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, which were converted by acidic hydrolysis with MeOH-HCl into their corresponding optically active (35,6R,7R,7aS)-3-substituted-6,7-dihydroxy-l-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.