(R)-tert-butyl 2-(3-deuteriotetrahydro-2H-pyran-3-yl)hydrazinecarboxylate | 1315380-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (R)-tert-butyl 2-(3-deuteriotetrahydro-2H-pyran-3-yl)hydrazinecarboxylate
• CAS: 1315380-86-9
• 化学式: C₁₀H₂₀N₂O₃
• 分子量: 217.272
• InChiKey: FOBVQYVABFGEAZ-ZOYPIFFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(dihydro-2H-pyran-3(4H)-ylidene)hydrazine-1-carboxylate 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 MandyPhosTM M₀₀₂-1 、 氘 作用下， 以 甲醇 为溶剂， 30.0 ℃ 、2.07 MPa 条件下， 反应 20.0h， 以93%的产率得到(R)-tert-butyl 2-(3-deuteriotetrahydro-2H-pyran-3-yl)hydrazinecarboxylate
  参考文献：
  名称：

  Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration

  摘要：

  An enantioselective hydrogenation of hydrazones derived from heterocyclic ketones was developed with up to 85% ee. The enantiomeric purity was enriched to >99% ee by crystallization from EtOAc in >80% yield. Optimization studies have revealed a notable solvent effect that resulted in inversion of enantioselectivity from 85% ee in MeOH to -27% ee in DCE. The hydrazone geometry and possible hydrogenation via endocyclic alkene were examined as possible factors for the inversion of enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.017