ethyl 2-nitro-5-oxopentanoate | 794528-56-6

• 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: ethyl 2-nitro-5-oxopentanoate
• 英文别名: 2-nitro-5-oxo-valeric acid ethyl ester；2-Nitro-5-oxo-valeriansaeure-aethylester；Ethyl 2-nitro-5-oxopentanoate
• CAS: 794528-56-6
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: FYICPWVFHSQXTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitro-5-oxopentanoate 在 platinum(IV) oxide 、 sodium hydroxide 、 rabbit muscle fructose-1,6-diphosphate aldolase EC 4.1.2.13 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 20.0~30.0 ℃ 、344.74 kPa 条件下， 反应 120.0h， 生成 (1S,2S,3R,6R)-6-amino-1-hydroxymethyl-cyclohexane-1,2,3-triol
  参考文献：
  名称：

  A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction

  摘要：

  The reactions of 4-nitroaldehydes 9 and 10 with dihydroxyacetonephosphate (DHAP) catalyzed by fructose-1,6-diphosphate aldolase from rabbit muscle were studied. Starting from 9 or 10, only one main stereomer of nitrocyclitol 8 was isolated. A highly stereoselective intramolecular cyclization (Henry reaction or nitroaldol reaction) took place under acidic conditions during the aldolase catalyzed condensation and phytase catalyzed phosphate hydrolysis coupled step. The catalytic hydrogenation of nitrocyclitol 8 yielded aminocyclitol 7, a valiolamine analogue. Its inhibition properties were evaluated towards five glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.029
• 作为产物：
  描述：

  ethyl 5,5-dimethoxy-2-nitropentanoate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 ethyl 2-nitro-5-oxopentanoate
  参考文献：
  名称：

  A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction

  摘要：

  The reactions of 4-nitroaldehydes 9 and 10 with dihydroxyacetonephosphate (DHAP) catalyzed by fructose-1,6-diphosphate aldolase from rabbit muscle were studied. Starting from 9 or 10, only one main stereomer of nitrocyclitol 8 was isolated. A highly stereoselective intramolecular cyclization (Henry reaction or nitroaldol reaction) took place under acidic conditions during the aldolase catalyzed condensation and phytase catalyzed phosphate hydrolysis coupled step. The catalytic hydrogenation of nitrocyclitol 8 yielded aminocyclitol 7, a valiolamine analogue. Its inhibition properties were evaluated towards five glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.029

文献信息

• Gamma-nitro-gamma-carbalkoxy butyraldehydes and process
  申请人：GEN MILLS INC

  公开号：US02599653A1

  公开（公告）日：1952-06-10