Tert-butyl 6-chloro-3-cyano-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate | 1007362-97-1

• 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 6-chloro-3-cyano-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate
• CAS: 1007362-97-1
• 化学式: C₂₀H₂₃ClN₂O₂
• 分子量: 358.868
• InChiKey: YJJQFNNOSPIPAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 6-chloro-3-cyano-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 生成 5-Chloro-6-methylspiro[indene-3,4'-piperidine]-1-carbonitrile
  参考文献：
  名称：

  Asymmetric bioreduction of α,β-unsaturated nitriles and ketones

  摘要：

  Two applications for the asymmetric reduction of activated alkenes employing isolated enoate reductases are reported. A series of alpha,beta-unsturated nitriles were shown to be converted to the optically active nitrile products in high yields and excellent enantioselectivities (up to 99% ee). In addition, the reduction of 2,3-disubstituted cyclopenteriones was shown to provide almost exclusively trans-2,3-disubstituted cyclopentanones in high yield and enantiopurity (94% ee). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.023
• 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 生成 Tert-butyl 6-chloro-3-cyano-5-methylspiro[indene-1,4'-piperidine]-1'-carboxylate 、 Tert-butyl 4-chloro-3-cyano-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.
• Asymmetric bioreduction of α,β-unsaturated nitriles and ketones
  作者：Birgit Kosjek、Fred J. Fleitz、Peter G. Dormer、Jeffrey T. Kuethe、Paul N. Devine

  DOI：10.1016/j.tetasy.2008.05.023

  日期：2008.6

  Two applications for the asymmetric reduction of activated alkenes employing isolated enoate reductases are reported. A series of alpha,beta-unsturated nitriles were shown to be converted to the optically active nitrile products in high yields and excellent enantioselectivities (up to 99% ee). In addition, the reduction of 2,3-disubstituted cyclopenteriones was shown to provide almost exclusively trans-2,3-disubstituted cyclopentanones in high yield and enantiopurity (94% ee). (C) 2008 Elsevier Ltd. All rights reserved.