10-chloro-2t-methyl-11b-phenyl-(11br)-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one | 24143-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 10-chloro-2t-methyl-11b-phenyl-(11br)-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one
• 英文别名: (+/-)trans-10-Chlor-2r-methyl-11bt-phenyl-2,3,5,6,7,11b-hexahydro-benzo<6,7>-1,4-diazepino<5,4-b>oxazol-6-on；(+/-)trans-10-Chlor-2-methyl-11b-phenyl-2,3,5,6,7,11b-hexahydro-benzo<6,7>-1,4-diazepino<5,4-b>oxazol-6-on；trans-oxazolazepam；trans-oxazolam；(2S,11bR)-10-chloro-2-methyl-11b-phenyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
• CAS: 24143-17-7；27167-30-2；27172-76-5；102916-80-3；102916-81-4；102916-82-5；102916-83-6
• 化学式: C₁₈H₁₇ClN₂O₂
• 分子量: 328.798
• InChiKey: VCCZBYPHZRWKFY-KPZWWZAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-chloro-2t-methyl-11b-phenyl-(11br)-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one 生成 7-benzyl-10-chloro-2t-methyl-11b-phenyl-(11br)-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one
  参考文献：
  名称：

  抗焦虑镇静剂。1.苯并[6,7] -1,4-二氮杂[5,4-b]恶唑衍生物及其类似物的合成及药理作用。

  摘要：

  DOI：

  10.1021/jm00288a015
• 作为产物：
  描述：

  2-溴乙酰胺-5-氯苯甲酮 、 异丙醇胺 生成 10-chloro-2t-methyl-11b-phenyl-(11br)-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one
  参考文献：
  名称：

  抗焦虑镇静剂。1.苯并[6,7] -1,4-二氮杂[5,4-b]恶唑衍生物及其类似物的合成及药理作用。

  摘要：

  DOI：

  10.1021/jm00288a015

文献信息

• cis/trans Isomerization rate of oxazolam in organic solvents measured by high-performance liquid chromatography.
  作者：Yukihisa KURONO、Yasuhiro JINNO、Tomonari KUWAYAMA、Naomi SATO、Tamotsu YASHIRO、Ken IKEDA

  DOI：10.1248/cpb.37.1044

  日期：——

  Diastereoisomers of oxazolam (2R-cis, 2R-trans, 2S-cis, and 2S-trans isomers) were resolved and assigned by high-performance liquid chromatography (HPLC). By means of HPLC the cis/trans isomerization rates of oxazolam in some organic solvents could be measured, although such rate measurements had previously been attempted only by an nuclear magnetic resonance (NMR) method and it was reported that in most organic solvents the isomerization was too fast to allow the rates to be measured. In some cases (depending on the lot number of the solvent), rapid isomerization was observed in chloroform-d (the ratio of cis isomer to trans isomer (2 : 3) did not change with time, that is, the isomerization was at equilibrium immediately after dissolution of oxazolam in the CDCI3). This fast isomerization was suggested to be catalyzed by an acid contaminant, since the iminium intermediate of oxazolam was detected in the reaction solution by fluorescence spectroscopy.

  通过高效液相色谱法（HPLC）解析并确定了恶唑仑的消旋异构体（2R-cis、2R-trans、2S-cis和2S-trans异构体）。通过HPLC可以测量恶唑仑在某些有机溶剂中的顺式/反式异构化率，尽管此前仅通过核磁共振（NMR）方法尝试过测量这种速率，并且有报道称在大多数有机溶剂中异构化速度太快，无法测量速率。在某些情况下（取决于溶剂的批号），在氯仿-d中观察到快速异构化（顺式异构体与反式异构体的比率（2：3）不会随时间变化，也就是说，在恶唑仑溶解在CDCI3中后，异构化立即达到平衡）。这种快速异构化被认为是由一种酸性污染物催化的，因为在反应溶液中通过荧光光谱检测到了恶唑仑的亚氨基中间体。