(1S,2R)-2-nitro-1-(thiophen-2-yl)butan-1-ol | 1239610-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1S,2R)-2-nitro-1-(thiophen-2-yl)butan-1-ol
• 英文别名: (1S,2R)-2-nitro-1-thiophen-2-ylbutan-1-ol
• CAS: 1239610-56-0
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: GIFCCXNTVBZYTK-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 硝基丙烷 在 N-甲基吗啉 、 C₃₁H₃₃CuF₆N₅O₆S₂ 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 (1S,2R)-2-nitro-1-(thiophen-2-yl)butan-1-ol 、 C₈H₁₁NO₃S
  参考文献：
  名称：

  CuII–双咪唑啉催化的高度同硝基硝基硝基醇反应

  摘要：

  催化亨利（Henry）：发现在N-甲基吗啉为碱的存在下，手性双咪唑啉1 -Cu（OTf）2能以高合成和对映选择性的方式有效催化多种醛（包括芳族化合物）的硝基醛反应。杂芳族，α，β-不饱和和脂肪族醛（请参见方案）。

  DOI：

  10.1002/chem.201000650

文献信息

• Synthesis and computation of diastereomeric phenanthroline–quinine ligands and their application in asymmetric Henry reaction
  作者：Lili Zhang、Hao Wu、Zhongyue Yang、Xiufang Xu、Haitao Zhao、Yaodong Huang、Yongmei Wang

  DOI：10.1016/j.tet.2013.10.010

  日期：2013.12

  A class of chiral ligands has been developed by combining phenanthroline with quinine in a one-step method that does not require resolution. The synthesized three ligands were then coordinated with Cu-(II) and the performance of the resultant chiral catalysts in the asymmetric Henry reaction was evaluated. Moderate to good yields (up to 86%) with high enantioselectivities (up to 99% ee) were observed in the reactions catalyzed by one of the three catalysts. Theoretical calculations were performed to analyze the catalytic activities of the different Cu-(II)-ligand catalysts. Three different ligands were investigated and one ligand was found to adopt an unexpected five-coordinated mode; the second coordinated with two nitrogen atoms of phenanthroline to give a complex, which activated both substrates of Henry reaction; the third was unable to form a complex with Cu-(II). (C) 2013 Elsevier Ltd. All rights reserved.