(2R,3R)-3-(1,3-dioxolan-2-yl)-2-nitromethyl-hex-5-enoic acid methyl ester | 1087041-30-2

• 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: (2R,3R)-3-(1,3-dioxolan-2-yl)-2-nitromethyl-hex-5-enoic acid methyl ester
• CAS: 1087041-30-2
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: XDAPEGOTMNUEQI-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  87.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(1,3-dioxolan-2-yl)-2-nitromethyl-hex-5-enoic acid methyl ester 在 三甲基氯硅烷 、 三乙胺 、 六甲基磷酰三胺 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以50%的产率得到(3aR,5R,6R)-5-(1,3-dioxolan-2-yl)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids

  摘要：

  We propose an asymmetric synthesis of functionalized cyclopentanoids bearing up to four stereogenic centers from easily accessible nitroalkenes and unsaturated aldehydes. The overall sequence includes an enantioselective organocatalytic Michael addition and a [3 + 2]-heterocyclization between an in situ generated silyInitronate and the unactivated double bond. Finally, the fused isoxazoline can be further transformed to various cyclopentanoids.

  DOI：

  10.1021/ol8023133
• 作为产物：
  描述：

  (2R,3R)-3-formyl-2-nitromethylhex-5-enoic acid methyl ester 、 乙二醇 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 苯 为溶剂， 以65%的产率得到(2R,3R)-3-(1,3-dioxolan-2-yl)-2-nitromethyl-hex-5-enoic acid methyl ester
  参考文献：
  名称：

  Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids

  摘要：

  We propose an asymmetric synthesis of functionalized cyclopentanoids bearing up to four stereogenic centers from easily accessible nitroalkenes and unsaturated aldehydes. The overall sequence includes an enantioselective organocatalytic Michael addition and a [3 + 2]-heterocyclization between an in situ generated silyInitronate and the unactivated double bond. Finally, the fused isoxazoline can be further transformed to various cyclopentanoids.

  DOI：

  10.1021/ol8023133