tert-butyl-[4-[(5R)-4,5-dihydro-1,2-oxazol-5-yl]butoxy]-diphenylsilane | 1161512-55-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-[4-[(5R)-4,5-dihydro-1,2-oxazol-5-yl]butoxy]-diphenylsilane
• CAS: 1161512-55-5
• 化学式: C₂₃H₃₁NO₂Si
• 分子量: 381.59
• InChiKey: CZEKDTRRKYQNPZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[4-[(5R)-4,5-dihydro-1,2-oxazol-5-yl]butoxy]-diphenylsilane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以96%的产率得到(R)-7-(tert-butyldiphenylsilyloxy)-3-hydroxyheptanenitrile
  参考文献：
  名称：

  Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals

  摘要：

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

  DOI：

  10.1021/jo1013788
• 作为产物：
  描述：

  7-{[tert-Butyl(diphenyl)silyl]oxy}hept-2-enal 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 苯甲酸 、 丙酮肟 、 甲醇 、 硫酸 作用下， 以 甲苯 为溶剂， 生成 tert-butyl-[4-[(5R)-4,5-dihydro-1,2-oxazol-5-yl]butoxy]-diphenylsilane
  参考文献：
  名称：

  Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals

  摘要：

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

  DOI：

  10.1021/jo1013788

文献信息

• Enantioselective Synthesis of 2-Isoxazolines by a One-Flask Conjugate Addition/Oxime-Transfer Process
  作者：Antti Pohjakallio、Petri M. Pihko

  DOI：10.1002/chem.200802684

  日期：2009.4.14

  Enantioselective isoxazoline synthesis: A combination of 1) a catalytic enantioselective conjugate addition of oximes to α,β‐unsaturated aldehydes and 2) an acid‐catalyzed intramolecular oxime‐transfer reaction lead to the first asymmetric synthesis of 3‐unsubstituted 2‐isoxazolines (see scheme).

  对映选择性异恶唑啉合成：1）肟对α，β-不饱和醛的催化对映选择性共轭加成与2）酸催化的分子内肟转移反应的结合导致了3-未取代的2-异恶唑啉的首次不对称合成（参见方案）。
• Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of β-Hydroxynitriles from Enals
  作者：Antti Pohjakallio、Petri M. Pihko、Jun Liu

  DOI：10.1021/jo1013788

  日期：2010.10.1

  The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.