3-oxobutanoimidazolide ethylene ketal | 116149-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-oxobutanoimidazolide ethylene ketal
• 英文别名: 2-Methyl-1,3-dioxolanyl-(2)-essigsaeureimidazolid；1-Imidazol-1-yl-2-(2-methyl-1,3-dioxolan-2-yl)ethanone
• CAS: 116149-27-0
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: SFCFVXWTXALVGO-UHFFFAOYSA-N

物化性质

• 熔点：
  52-55 °C
• 沸点：
  333.4±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异丙基肼 、 3-oxobutanoimidazolide ethylene ketal 以 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  An Efficient and Practical Synthesis of Remogliflozin Etabonate, a Potent Inhibitor of Low-Affinity Na+-Dependent Glucose Co-Transporter (SGLT2)

  摘要：

  A practical process for the preparation of remogliflozin etabonate, a prodrug of the selective low-affinity Na+-dependent glucose co-transporter (SGLT2) inhibitor, remogliflozin, is described. We established a chemoselective synthetic route to 1,2-dihydro-4-[(4-isopropoxyphenypmethyl]-1-isopropyl-5-methyl-3H-pyrazol-3-one and an efficient O-glycosylation of this compound with 2,3,4,6-tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide. This synthetic process provided remogliflozin etabonate in a 39% overall yield from commercially available 4-isopropoxybenzaldehyde.

  DOI：

  10.3987/com-18-13881
• 作为产物：
  描述：

  (2-methyl-[1,3]dioxolan-2-yl)-acetic acid 在 草酰氯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 3-oxobutanoimidazolide ethylene ketal
  参考文献：
  名称：

  A 5C + 5C bicycloaromatization reaction via an aldol condensation cascade. A regioselective synthesis of functionalized naphthalenes from acyclic precursors

  摘要：

  DOI：

  10.1021/jo00256a002

文献信息

• Synthesis of α-unsubstituted aldol adducts utilizing enantiomerically pure β-keto δ-dioxolane sulfoxides
  作者：Frances Rose Blase、Hung Le

  DOI：10.1016/0040-4039(95)00853-5

  日期：1995.6

  We report an efficient means to synthesize either enantiomer of α-unsubstituted aldol adducts in high enantiomeric excess through the use of β-keto δ-dioxolane sulfoxide 4. Through a short sequence of reactions, α-unsubstituted aldol products are obtainable in high yield.

  我们报告了一种有效的方法，可以通过使用β-酮δ-二氧戊环亚砜4来合成高对映体过量的α-未取代的醛醇加合物的对映体。通过短的反应序列，可以高产率获得α-未取代的羟醛产物。
• STOSSEL, D.;CHAN, T. H., J. ORG. CHEM., 53,(1988) N 21, C. 4901-4908
  作者：STOSSEL, D.、CHAN, T. H.

  DOI：——

  日期：——
• A 5C + 5C bicycloaromatization reaction via an aldol condensation cascade. A regioselective synthesis of functionalized naphthalenes from acyclic precursors
  作者：D. Stossel、T. H. Chan

  DOI：10.1021/jo00256a002

  日期：1988.10
• An Efficient and Practical Synthesis of Remogliflozin Etabonate, a Potent Inhibitor of Low-Affinity Na+-Dependent Glucose Co-Transporter (SGLT2)
  作者：Masahiro Kobayashi、Takayuki Ainai

  DOI：10.3987/com-18-13881

  日期：——

  A practical process for the preparation of remogliflozin etabonate, a prodrug of the selective low-affinity Na+-dependent glucose co-transporter (SGLT2) inhibitor, remogliflozin, is described. We established a chemoselective synthetic route to 1,2-dihydro-4-[(4-isopropoxyphenypmethyl]-1-isopropyl-5-methyl-3H-pyrazol-3-one and an efficient O-glycosylation of this compound with 2,3,4,6-tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide. This synthetic process provided remogliflozin etabonate in a 39% overall yield from commercially available 4-isopropoxybenzaldehyde.