(S)-4-amino-6-benzyloxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-4-amino-6-benzyloxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran
• 英文别名: (4S)-2,2-dimethyl-6-phenylmethoxy-3,4-dihydrochromen-4-amine
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: APPZTNAPKBNODA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(benzyloxy)-2,2-dimethylchroman-4-one 生成 (S)-4-amino-6-benzyloxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran 、 (R)-4-amino-6-benzyloxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran
  参考文献：
  名称：

  Asymmetric synthesis of 4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans

  摘要：

  Highly enantioselective reduction of 3,4-dihydro-2,2-dimethyl-2H- 1 -benzopyran-4-ones 3 a-e by BH3 was achieved in the presence of catalytic amounts of Corey's oxazaborolidine 4 to afford the corresponding 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ols 2a-e in quantitative yields. These benzopyran-4-ols 2a-e were converted into the chiral 4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran 1a-e by mesylation, followed by introduction of an azide group by tetra-n-butyl-ammonium azide, and finally by reduction of the azide 6 with triphenylphosphine under very mild conditions without loss of stereo information. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00376-2

文献信息

• Asymmetric synthesis of 4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans
  作者：Andreas Burgard、Hans-Jochen Lang、Uwe Gerlach

  DOI：10.1016/s0040-4020(99)00376-2

  日期：1999.6

  Highly enantioselective reduction of 3,4-dihydro-2,2-dimethyl-2H- 1 -benzopyran-4-ones 3 a-e by BH3 was achieved in the presence of catalytic amounts of Corey's oxazaborolidine 4 to afford the corresponding 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ols 2a-e in quantitative yields. These benzopyran-4-ols 2a-e were converted into the chiral 4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran 1a-e by mesylation, followed by introduction of an azide group by tetra-n-butyl-ammonium azide, and finally by reduction of the azide 6 with triphenylphosphine under very mild conditions without loss of stereo information. (C) 1999 Elsevier Science Ltd. All rights reserved.