(R)-1-[(S)-chroman-2-yl]ethane-1,2-diol | 1177405-74-1

• 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)-1-[(S)-chroman-2-yl]ethane-1,2-diol
• 英文别名: (R)-1-(S)-chroman-2yl-ethane-1,2-diol；(1R)-1-[(2S)-3,4-dihydro-2H-chromen-2-yl]ethane-1,2-diol
• CAS: 1177405-74-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MNUGGHAYBYTGNZ-KOLCDFICSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  382.8±17.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-[(S)-chroman-2-yl]ethane-1,2-diol 在 吡啶 、 盐酸 、 palladium 10% on activated carbon 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 、 环己烯 为溶剂， 反应 11.0h， 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 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 D-(-)-酒石酸二乙酯 、 水 、 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 、 甲苯 为溶剂， 反应 34.5h， 生成 (R)-1-[(S)-chroman-2-yl]ethane-1,2-diol
  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

• Application of Phenolate Ion Mediated Intramolecular Epoxide Ring Opening in the Enantioselective Synthesis of Functionalized 2,3-Dihydrobenzofurans and 1-Benzopyrans¹
  作者：Gautam Panda、Subal Dinda、Sajal Das

  DOI：10.1055/s-0028-1088077

  日期：2009.6

  The enantioselective synthesis of 2-isopropenyl-2,3-dihydrobenzofurans, 4-(2,3-dihydrobenzofuran-2-yl)-2-methylbut-3-en-2-ols, 2-hydroxymethyl chromans, and 4-chroman-2-yl-2-methylbut-3-en-2-ols has been achieved using Sharpless asymmetric epoxidation-derived enantiomerically enriched epoxy alcohols as chiral building blocks. A phenolate ion mediated intramolecular epoxide ring-opening reaction was

  对映选择性合成2-异丙烯基-2,3-二氢苯并呋喃，4-（2,3-二氢苯并呋喃-2-基）-2-甲基丁-3-烯-2-醇，2-羟甲基苯并二氢吡喃和4-苯并二氢吡喃-使用Sharpless不对称环氧化衍生的对映异构体富集的环氧醇作为手性结构单元，可以实现2-yl-2-甲基but-3-en-2-ols。酚盐离子介导的分子内环氧化物开环反应是每个环化反应的关键步骤。 2-异丙烯基-2,3-二氢苯并呋喃-2-羟甲基苯并二氢吡喃-环氧化-环氧化物-多环化合物-开环 CDRI通信号码7184。
• 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.