methyl (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate | 891193-74-1

• 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 (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate
• 英文别名: methyl (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 891193-74-1
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: MQLNPLUEULVAGD-YKCGFPGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  methyl (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以66%的产率得到(3aR,4R,6aS)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 在 重铬酸吡啶 、 3 A molecular sieve 、 溶剂黄146 、 苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 methyl (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006

文献信息

• Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose
  作者：Nikolaos G. Argyropoulos、Theodoros D. Panagiotidis、John K. Gallos

  DOI：10.1016/j.tetasy.2006.02.006

  日期：2006.3

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.