(S)-2-cyano-1,4-benzodioxane | 1616377-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (S)-2-cyano-1,4-benzodioxane
• 英文别名: (3S)-2,3-dihydro-1,4-benzodioxine-3-carbonitrile
• CAS: 1616377-81-1
• 化学式: C₉H₇NO₂
• 分子量: 161.16
• InChiKey: DNLJHDDOVWQQEW-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-cyano-1,4-benzodioxane 在 sodium tetrahydroborate 、 sodium meta bi sulfate 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 21.5h， 生成 (S)-2-羟甲基-1,4-苯并二恶烷
  参考文献：
  名称：

  From 2-Aminomethyl-1,4-benzodioxane Enantiomers to Unichiral 2-Cyano- and 2-Carbonyl-Substituted Benzodioxanes via Dichloroamine

  摘要：

  2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).

  DOI：

  10.1021/jo500964y
• 作为产物：
  描述：

  (S)-2-N,N-dichloroaminomethyl-1,4-benzodioxane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以99.1%的产率得到
  参考文献：
  名称：

  From 2-Aminomethyl-1,4-benzodioxane Enantiomers to Unichiral 2-Cyano- and 2-Carbonyl-Substituted Benzodioxanes via Dichloroamine

  摘要：

  2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).

  DOI：

  10.1021/jo500964y

文献信息

• From 2-Aminomethyl-1,4-benzodioxane Enantiomers to Unichiral 2-Cyano- and 2-Carbonyl-Substituted Benzodioxanes via Dichloroamine
  作者：Cristiano Bolchi、Ermanno Valoti、Valentina Straniero、Paola Ruggeri、Marco Pallavicini

  DOI：10.1021/jo500964y

  日期：2014.7.18

  2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).