(2S)-2-[(2R)-oxiran-2-yl]-3,4-dihydro-2H-chromene

• 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: (2S)-2-[(2R)-oxiran-2-yl]-3,4-dihydro-2H-chromene
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: VECXQFNJFMVRGT-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2R)-oxiran-2-yl]-3,4-dihydro-2H-chromene 在 盐酸 、 palladium 10% on activated carbon 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 环己烯 为溶剂， 反应 10.0h， 生成 (R)-1-((R)-chroman-2-yl)-2-(((R)-2-((S)-chroman-2-yl)-2-hydroxyethyl)amino)ethan-1-ol hydrochloride
  参考文献：
  名称：

  Synthesis of Desfluorinated Nebivolol Isomers

  摘要：

  The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive beta-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.

  DOI：

  10.1021/acs.joc.5b00263
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 D-(-)-酒石酸二乙酯 、 水 、 sodium methylate 、 二异丁基氢化铝 、 三苯基膦 、 红铝 、 sodium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 正壬烷 、 正己烷 、 二氯甲烷 、 水 、 乙二醇 、 异丙醇 、 甲苯 为溶剂， 反应 35.5h， 生成 (2S)-2-[(2R)-oxiran-2-yl]-3,4-dihydro-2H-chromene
  参考文献：
  名称：

  Synthesis of Desfluorinated Nebivolol Isomers

  摘要：

  The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive beta-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.

  DOI：

  10.1021/acs.joc.5b00263

文献信息

• Synthesis of Desfluorinated Nebivolol Isomers
  作者：Purushothama Chary Khandavalli、Oliver Spiess、Oliver M. Böhm、Ilia Freifeld、Kurt Kesseler、Gerhard Jas、Dieter Schinzer

  DOI：10.1021/acs.joc.5b00263

  日期：2015.4.17

  The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive beta-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.