(4S)-7-chloro-3,4-dihydro-2H-chromen-4-ol | 197908-45-5

• 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: (4S)-7-chloro-3,4-dihydro-2H-chromen-4-ol
• CAS: 197908-45-5
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: CTDYKWYKIBZVPN-QMMMGPOBSA-N

物化性质

• 沸点：
  300.0±40.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7-chlorochromone 在 甲酸 、 C₃₁H₃₅ClN₂O₂RhS^(1-) 、 sodium formate 作用下， 以 水 为溶剂， 反应 3.0h， 以99%的产率得到(4S)-7-chloro-3,4-dihydro-2H-chromen-4-ol
  参考文献：
  名称：

  Rh(II)-Cp∗–TsDPEN catalyzed aqueous asymmetric transfer hydrogenation of chromenones into saturated alcohol: CC and CO reduction in one step

  摘要：

  As an efficient catalyst for asymmetric transfer hydrogenation reaction (ATH reaction) of alpha,beta-unsaturated ketones, Rh-Cp*-TsDPEN (Cp* = 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenyl- ethylenediamine) shows high chemoselectivity on C=O and C=C reduction. In our method, both C=O and C=C bonds in a variety of chromenone derivatives were reduced efficiently in aqueous media, resulting in at least 98% ee and up to 99% yields in a convenient way without further purification. The product was a useful intermediate for deriving chiral chroman-4-amine, which was reported as an effective agent against hypotension and inflammatory pain by inhibiting human bradykinin B1 receptor. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.04.050

文献信息

• Rh(II)-Cp∗–TsDPEN catalyzed aqueous asymmetric transfer hydrogenation of chromenones into saturated alcohol: CC and CO reduction in one step
  作者：Lei Tang、Zechao Lin、Qiwei Wang、Xiaobei Wang、Linfeng Cun、Weicheng Yuan、Jin Zhu、Jingen Deng

  DOI：10.1016/j.tetlet.2012.04.050

  日期：2012.7

  As an efficient catalyst for asymmetric transfer hydrogenation reaction (ATH reaction) of alpha,beta-unsaturated ketones, Rh-Cp*-TsDPEN (Cp* = 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenyl- ethylenediamine) shows high chemoselectivity on C=O and C=C reduction. In our method, both C=O and C=C bonds in a variety of chromenone derivatives were reduced efficiently in aqueous media, resulting in at least 98% ee and up to 99% yields in a convenient way without further purification. The product was a useful intermediate for deriving chiral chroman-4-amine, which was reported as an effective agent against hypotension and inflammatory pain by inhibiting human bradykinin B1 receptor. (C) 2012 Published by Elsevier Ltd.