methyl 3-(5-acetyl-2,2-dimethyl-1,3-dioxol-4-yl)propionate | 923590-94-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(5-acetyl-2,2-dimethyl-1,3-dioxol-4-yl)propionate
• 英文别名: methyl 3-(5-acetyl-2,2-dimethyl-1,3-dioxol-4-yl)propanoate；Methyl 3-(5-acetyl-2,2-dimethyl-2H-1,3-dioxol-4-yl)propanoate
• CAS: 923590-94-7
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: YWOJPEGBZQVELP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-(2,3-O-isopropylidene-β-D-ribofuranosyl)acetate 在 咪唑 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲苯 、 苯 为溶剂， 反应 3.0h， 生成 methyl 3-(5-acetyl-2,2-dimethyl-1,3-dioxol-4-yl)propionate
  参考文献：
  名称：

  Uncommon transformations of methyl (1S,2S,3R,4R)-2,3-isopropylidenedioxy-5-iodomethyl-2-tetrahydrofurylacetate initiated by bases

  摘要：

  Methyl (I S,2S,3R,4R)-2,3-isopropylidenedioxy-5-iodomethyl-2-tetrahydrofurylacetate prepared in two stages from D-ribose acetonide underwent a series of uncommon transformations under the treatment with bases providing the following different products depending on the base applied: methyl 3-(5-acetyl-2,2-dimethyl- 1,3-dioxol-4-yl)propionate (DBU), methyl 2,3-isopropybdenedioxy-7-oxabicyclo[2.2.1]heptane-6-carboxylate (t-BuOK), methyl {(5R)-2,2-dimethyl-5-[(2R)-oxiranyl]-1,3-dioxolan-4-ylidene}propionate and methyl-(E)-3-{(4S,5R)-2,2-dimethyl-5-[(IR)-(2-oxiranyl)]-1,3-dioxolan-4-yl}-2-propenoate (t-BuOK and LDA).

  DOI：

  10.1134/s1070428006110169

文献信息

• Unexpected transformation of methyl 3,6-anhydro-2,7-dideoxy-7-iodo-4,5-O-isopropylidene-D-allo-heptonate in the dehydroiodination reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene
  作者：N. A. Ivanova、Z. R. Valiullina、O. V. Shitikova、M. S. Miftakhov

  DOI：10.1007/s11172-006-0179-1

  日期：2005.11

  The reaction of methyl 3,6-anhydro-2,7-dideoxy-7-iodo-4,5-O-isopropylidene-D-allo-heptonate with 1,8-diazabicyclo[5.4.0]undec-7-ene affords methyl 3,6-anhydro-2,7-dideoxy-4,5-O-isopropylidene-D-ribo-hept-6-enonate, which undergoes the previously unknown rearrangement into a 2,2-dimethyl-1,3-dioxole derivative.

  3,6-脱水-2,7-二脱氧-7-碘-4,5-O-异亚丙基-D-别庚酸甲酯与1,8-二氮杂双环[5.4.0]十一碳-7-烯的反应生成3,6-脱水-2,7-二脱氧-4,5-O-异亚丙基-D-核糖-庚-6-烯酸甲酯，后者经历先前未知的重排反应，生成2,2-二甲基-1,3-二氧杂环戊烯衍生物。
• Uncommon transformations of methyl (1S,2S,3R,4R)-2,3-isopropylidenedioxy-5-iodomethyl-2-tetrahydrofurylacetate initiated by bases
  作者：N. A. Ivanova、Z. R. Valiullina、O. V. Shitikova、M. S. Miftakhov

  DOI：10.1134/s1070428006110169

  日期：2006.11

  Methyl (I S,2S,3R,4R)-2,3-isopropylidenedioxy-5-iodomethyl-2-tetrahydrofurylacetate prepared in two stages from D-ribose acetonide underwent a series of uncommon transformations under the treatment with bases providing the following different products depending on the base applied: methyl 3-(5-acetyl-2,2-dimethyl- 1,3-dioxol-4-yl)propionate (DBU), methyl 2,3-isopropybdenedioxy-7-oxabicyclo[2.2.1]heptane-6-carboxylate (t-BuOK), methyl (5R)-2,2-dimethyl-5-[(2R)-oxiranyl]-1,3-dioxolan-4-ylidene}propionate and methyl-(E)-3-(4S,5R)-2,2-dimethyl-5-[(IR)-(2-oxiranyl)]-1,3-dioxolan-4-yl}-2-propenoate (t-BuOK and LDA).