(E)-triisopropyl(4-nitrobut-3-en-1-yn-1-yl)silane

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-triisopropyl(4-nitrobut-3-en-1-yn-1-yl)silane
• 英文别名: [(E)-4-nitrobut-3-en-1-ynyl]-tri(propan-2-yl)silane
• 化学式: C₁₃H₂₃NO₂Si
• 分子量: 253.417
• InChiKey: YDJARDVRDNKKEG-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-triisopropyl(4-nitrobut-3-en-1-yn-1-yl)silane 、 2-呋喃基羟基甲基甲酮 在 chiral proline-derived zinc magnesium 作用下， 以 正庚烷 、 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 、 (2S,3S)-1-Furan-2-yl-2-hydroxy-3-nitromethyl-5-triisopropylsilanyl-pent-4-yn-1-one
  参考文献：
  名称：

  A Heterodinuclear Asymmetric Catalyst for Conjugate Additions of α-Hydroxyketones to β-Substituted Nitroalkenes

  摘要：

  The bis- ProPhenol ligand was designed to facilitate formation of hetereodinuclear complexes based upon the large difference in p K a of the one phenolic OH group to the tertiary OH groups. In exploring the first example of hydroxyacetophenones as donors in asymmetric Michael reactions with nitroalkene acceptors, the best stereocontrol was observed with a zinc/ magnesium dinuclear complex where enantiomeric excesses ranged up to 92% for the major anti diastereomer.

  DOI：

  10.1021/ol062485n

文献信息

• Highly Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic Acid Derivatives Catalyzed by a Dinuclear Zinc Complex
  作者：Barry M. Trost、Keiichi Hirano

  DOI：10.1002/anie.201201116

  日期：2012.6.25

  dinuclear zinc–ProPhenol catalyst enables highly enantioselective nitro‐Michael reactions with oxazol‐4(5H)‐ones as nucleophilic substrates (see scheme, Nap=2‐naphthyl). This work highlights the utility of the ProPhenol family of ligands. The modular nature of these ligands proved crucial in the optimization of reaction conditions to achieve excellent stereoselectivities.

  双核锌-ProPhenol催化剂可与作为亲核底物的恶唑-4（5 H）-酮进行高度对映选择性的硝基-迈克尔反应（请参阅方案，Nap = 2-萘基）。这项工作突出了ProPhenol配体家族的实用性。这些配体的模块性质被证明对于优化反应条件以实现出色的立体选择性至关重要。
• A Heterodinuclear Asymmetric Catalyst for Conjugate Additions of α-Hydroxyketones to β-Substituted Nitroalkenes
  作者：Barry M. Trost、Soleiman Hisaindee

  DOI：10.1021/ol062485n

  日期：2006.12.1

  The bis- ProPhenol ligand was designed to facilitate formation of hetereodinuclear complexes based upon the large difference in p K a of the one phenolic OH group to the tertiary OH groups. In exploring the first example of hydroxyacetophenones as donors in asymmetric Michael reactions with nitroalkene acceptors, the best stereocontrol was observed with a zinc/ magnesium dinuclear complex where enantiomeric excesses ranged up to 92% for the major anti diastereomer.