(R)-2-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine | 119746-91-7

• 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: (R)-2-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine
• 英文别名: (2R)-2-(Chloromethyl)-2,3-dihydro-1,4-benzodioxin；(3R)-3-(chloromethyl)-2,3-dihydro-1,4-benzodioxine
• CAS: 119746-91-7
• 化学式: C₉H₉ClO₂
• mdl: MFCD00014666
• 分子量: 184.622
• InChiKey: AYPKYQSHFKQVDL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-O-[2-[[(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl-methylamino]ethyl] 3-O-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  New 1,4-dihydropyridine derivatives combining calcium antagonism and .alpha.-adrenolytic properties

  摘要：

  A series of twelve 1,4-dihydropyridine derivatives incorporating an alpha-adrenergic moiety in one of the ester chains was synthesized. The compounds were evaluated for their calcium antagonist activities by the inhibition of [3H]nitrendipine binding and, in vitro, on pig coronary artery. Their alpha 1- and alpha 2-adrenolytic effects were assessed from their inhibition of [3H]prazosin and [3H]yohimbine binding and, in vitro, on rat aorta and guinea pig vas deferens. Compounds 6 and 9-11 displayed strong calcium antagonist activities, identical with that of nicardipine. The moderate alpha-adrenolytic properties observed were attributed to the presence of alpha-adrenergic moieties. The four chiral derivatives 6a (R,R), 6b (S,S), 6c (S,R), and 6d (R,S) with an N-methyl-N-(benzodioxanylmethyl)amino group on the ester chain were prepared and tested as done previously. Some structure-activity relationships are discussed.

  DOI：

  10.1021/jm00126a042
• 作为产物：
  描述：

  (S)-2-羟甲基-1,4-苯并二恶烷 在 吡啶 、 氯化亚砜 作用下， 反应 3.0h， 以68%的产率得到(R)-2-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine
  参考文献：
  名称：

  New 1,4-dihydropyridine derivatives combining calcium antagonism and .alpha.-adrenolytic properties

  摘要：

  A series of twelve 1,4-dihydropyridine derivatives incorporating an alpha-adrenergic moiety in one of the ester chains was synthesized. The compounds were evaluated for their calcium antagonist activities by the inhibition of [3H]nitrendipine binding and, in vitro, on pig coronary artery. Their alpha 1- and alpha 2-adrenolytic effects were assessed from their inhibition of [3H]prazosin and [3H]yohimbine binding and, in vitro, on rat aorta and guinea pig vas deferens. Compounds 6 and 9-11 displayed strong calcium antagonist activities, identical with that of nicardipine. The moderate alpha-adrenolytic properties observed were attributed to the presence of alpha-adrenergic moieties. The four chiral derivatives 6a (R,R), 6b (S,S), 6c (S,R), and 6d (R,S) with an N-methyl-N-(benzodioxanylmethyl)amino group on the ester chain were prepared and tested as done previously. Some structure-activity relationships are discussed.

  DOI：

  10.1021/jm00126a042

文献信息

• Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl
  作者：Wen Yang、Zhaobin Wang、Jianwei Sun

  DOI：10.1002/anie.201601844

  日期：2016.6.6

  An unprecedented enantioselective oxetane opening with chloride provides access to a range of highly functionalized three‐carbon building blocks. The excellent enantiocontrol is enabled not only by a new catalyst, but also by the unusual use of wet molecular sieves for the controlled release of HCl.

  前所未有的带有氯的对映选择性氧杂环丁烷开口为人们提供了进入一系列高度功能化的三碳结构单元的途径。出色的对映体控制不仅可以通过新型催化剂实现，而且还可以通过湿法分子筛的不寻常使用来控制HCl的释放。
• MARCINIAK, GILBERT;DELGADO, ANTONIO;LECLERC, GERARD;VELLY, JEANNE;DECKER,+, J. MED. CHEM., 32,(1989) N, C. 1402-1407
  作者：MARCINIAK, GILBERT、DELGADO, ANTONIO、LECLERC, GERARD、VELLY, JEANNE、DECKER,+

  DOI：——

  日期：——
• New 1,4-dihydropyridine derivatives combining calcium antagonism and .alpha.-adrenolytic properties
  作者：Gilbert Marciniak、Antonio Delgado、Gerard Leclerc、Jeanne Velly、Nicole Decker、Jean Schwartz

  DOI：10.1021/jm00126a042

  日期：1989.6

  A series of twelve 1,4-dihydropyridine derivatives incorporating an alpha-adrenergic moiety in one of the ester chains was synthesized. The compounds were evaluated for their calcium antagonist activities by the inhibition of [3H]nitrendipine binding and, in vitro, on pig coronary artery. Their alpha 1- and alpha 2-adrenolytic effects were assessed from their inhibition of [3H]prazosin and [3H]yohimbine binding and, in vitro, on rat aorta and guinea pig vas deferens. Compounds 6 and 9-11 displayed strong calcium antagonist activities, identical with that of nicardipine. The moderate alpha-adrenolytic properties observed were attributed to the presence of alpha-adrenergic moieties. The four chiral derivatives 6a (R,R), 6b (S,S), 6c (S,R), and 6d (R,S) with an N-methyl-N-(benzodioxanylmethyl)amino group on the ester chain were prepared and tested as done previously. Some structure-activity relationships are discussed.