(R)-6-fluoro-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol

• 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: (R)-6-fluoro-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol
• 英文别名: (4R)-6-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-ol；(4R)-6-fluoro-2,2-dimethyl-3,4-dihydrochromen-4-ol
• 化学式: C₁₁H₁₃FO₂
• 分子量: 196.221
• InChiKey: BEZSNFOXBWMXRK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氟-2,3-二氢-2,2-二甲基色烯-4-酮 在 硼烷 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (R)-6-fluoro-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol 、 (S)-6-fluoro-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol
  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.