(2R,3R)-3-formyl-2-nitromethylhex-5-enoic acid methyl ester | 1087041-13-1

• 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: (2R,3R)-3-formyl-2-nitromethylhex-5-enoic acid methyl ester
• 英文别名: methyl (2R,3R)-3-formyl-2-(nitromethyl)hex-5-enoate
• CAS: 1087041-13-1
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: VALQQNWTMIMFQS-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-戊烯醛 、 methyl 3-nitroacrylate 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 苯甲酸 作用下， 以 水 为溶剂， 生成 (2R,3R)-3-formyl-2-nitromethylhex-5-enoic acid methyl ester 、 3-formyl-2-nitromethylhex-5-enoic acid methyl ester 、 3-formyl-2-nitromethylhex-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

文献信息

• Sequential Organocatalyzed Michael Addition/[3 + 2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids
  作者：Damien Bonne、Lydie Salat、Jean-Pierre Dulcère、Jean Rodriguez

  DOI：10.1021/ol8023133

  日期：2008.12.4

  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.