5-acetoxy-4-oxopentanal-4-ethylene glycol ketal | 54214-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetoxy-4-oxopentanal-4-ethylene glycol ketal
• 英文别名: 1,3-Dioxolane-2-propanal, 2-[(acetyloxy)methyl]-；[2-(3-oxopropyl)-1,3-dioxolan-2-yl]methyl acetate
• CAS: 54214-75-4
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: DKDQRPNTJYQLCI-UHFFFAOYSA-N

物化性质

• 沸点：
  299.0±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetoxy-4-oxopentanal-4-ethylene glycol ketal 在 盐酸 、 lithium tetrafluoroborate 、 magnesium sulfate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 58.17h， 生成 benzyl 2-[(2S,5R,11S)-8-(acetyloxymethyl)-3-oxo-11-phenyl-9-oxa-1,4-diazatricyclo[6.3.0.02,5]undecan-4-yl]-2-diethoxyphosphorylacetate
  参考文献：
  名称：

  Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays

  摘要：

  A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.

  DOI：

  10.1021/jo00046a030
• 作为产物：
  描述：

  1-acetoxy-5-hexen-2-one ethylene glycol ketal 在 sodium periodate 、 osmium (III) chloride 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.5h， 以61%的产率得到5-acetoxy-4-oxopentanal-4-ethylene glycol ketal
  参考文献：
  名称：

  Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays

  摘要：

  A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.

  DOI：

  10.1021/jo00046a030

文献信息

• US4226866A
  申请人：——

  公开号：US4226866A

  公开（公告）日：1980-10-07
• US4957912A
  申请人：——

  公开号：US4957912A

  公开（公告）日：1990-09-18
• Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays
  作者：Y. Narukawa、K. N. Juneau、D. Snustad、D. B. Miller、L. S. Hegedus

  DOI：10.1021/jo00046a030

  日期：1992.9

  A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.