(R)-tert-butyl 2-(tetrahydro-2H-pyran-3-yl)hydrazinecarboxylate | 1315380-81-4

• 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-(tetrahydro-2H-pyran-3-yl)hydrazinecarboxylate
• 英文别名: tert-butyl N-[[(3R)-oxan-3-yl]amino]carbamate
• CAS: 1315380-81-4
• 化学式: C₁₀H₂₀N₂O₃
• 分子量: 216.28
• InChiKey: FOBVQYVABFGEAZ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢-2H-吡喃-3-酮 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 MandyPhosTM M₀₀₂-1 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 20.0~30.0 ℃ 、2.07 MPa 条件下， 反应 22.0h， 生成 (R)-tert-butyl 2-(tetrahydro-2H-pyran-3-yl)hydrazinecarboxylate 、 (R)-tert-butyl 2-(tetrahydro-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

文献信息

• Catalytic asymmetric hydrogenation of heterocyclic ketone-derived hydrazones, pronounced solvent effect on the inversion of configuration
  作者：Nizar Haddad、Bo Qu、Sonia Rodriguez、Lars van der Veen、Diana C. Reeves、Nina C. Gonnella、Heewon Lee、Nelu Grinberg、Shengli Ma、Dhileepkumar Krishnamurthy、Tobias Wunberg、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2011.05.017

  日期：2011.7

  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.