Tert-butyl 3-(2-aminopropan-2-yl)-6-chloro-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate | 1007362-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: Tert-butyl 3-(2-aminopropan-2-yl)-6-chloro-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate
• CAS: 1007362-99-3
• 化学式: C₂₂H₃₁ClN₂O₂
• 分子量: 390.953
• InChiKey: QYPFCNHQFCSSTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-(2-aminopropan-2-yl)-6-chloro-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate chiral phosphine ligand 、 氢气 作用下， 40.0 ℃ 、620.54 kPa 条件下， 反应 18.0h， 生成 、 tert-butyl (1R)-1-(2-aminopropan-2-yl)-5-chloro-6-methylspiro[1,2-dihydroindene-3,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation

  摘要：

  [GRAPHICS]Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(1)-Josiphos complex in THF under 500 psi of H(2) generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.

  DOI：

  10.1021/jo702429u
• 作为产物：
  描述：

  Tert-butyl 4-(3-chloro-4-methylphenyl)-4-(2-chloro-2-oxoethyl)piperidine-1-carboxylate 、 氰基磷酸二乙酯 、 二碳酸二叔丁酯 、 甲基锂 生成 Tert-butyl 3-(2-aminopropan-2-yl)-6-chloro-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation

  摘要：

  [GRAPHICS]Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(1)-Josiphos complex in THF under 500 psi of H(2) generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.

  DOI：

  10.1021/jo702429u

文献信息

• Synthesis of a Tertiary Carbinamide via a Novel Rh-Catalyzed Asymmetric Hydrogenation
  作者：John Limanto、C. Scott Shultz、Benjamin Dorner、Richard A. Desmond、Paul N. Devine、Shane W. Krska

  DOI：10.1021/jo702429u

  日期：2008.2.1

  [GRAPHICS]Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(1)-Josiphos complex in THF under 500 psi of H(2) generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.