奥沙唑仑 | 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
• 中文名称: 奥沙唑仑
• 中文别名: 苯基磷羧酸钙；恶唑仑
• 英文名称: oxazolam
• 英文别名: Hializan；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
• 化学式: C₁₈H₁₇ClN₂O₂
• 分子量: 328.798
• InChiKey: VCCZBYPHZRWKFY-UHFFFAOYSA-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：

  奥沙唑仑 生成 2-氨基-5-氯二苯甲酮
  参考文献：
  名称：

  WESTON, S. I.;JAPP, M.;PARTRIDGE, J.;OSSELTON, M. D., J. CHROMATOGR., 538,(1991) N, C. 277-284

  摘要：

  DOI：
• 作为产物：
  描述：

  10-chloro-2-methyl-11b-phenyl-3,5,6,7-tetrahydro-2H-[1,3]oxazolo[3,2-d][1,4]benzodiazepine 生成 奥沙唑仑
  参考文献：
  名称：

  MASIKO, TEHTSUDZIRO

  摘要：

  DOI：

文献信息

• Intermediates for tricyclic benzodiazepines
  申请人：Hoffmann-La Roche Inc.

  公开号：US03965151A1

  公开（公告）日：1976-06-22

  Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.

  描述了在三环苯二氮卓衍生物（“A”）中，1位位置带有一个氢氧基较低的烷基取代基，以及在苯二氮卓基团的4位和5位之间连接的杂环环。该杂环环将包含出现在苯二氮卓环的4位的氮原子，以及连接到苯二氮卓环5位的碳原子上的杂原子，该杂原子可能是氧或氮。“A”中带有新杂环环中的氧原子可以通过在酸催化剂存在下用环氧化合物处理相应的4,5-不饱和苯二氮卓制备而成。“A”中带有新杂环环中的氮或氧原子可以通过对应开放化合物的环化制备而成。“A”可用作镇静剂、肌肉松弛剂和抗惊厥剂。
• The acid-base equilibrium reaction of benzodiazepinooxazoles.
  作者：MASARU IKEDA、TSUNEJI NAGAI

  DOI：10.1248/cpb.30.3810

  日期：——

  The acid-base equilibrium reactions of oxazolam (10-chloro-2, 3, 5, 6, 7, 11b-hexahydro-2-methyl-11b-phenylbenzo [6, 7]-1, 4-diazepino [5, 4-b] oxazol-6-one) and thirteen other derivatives of 1, 4-benzodiazepinooxazole (BDOZ) were studied. Ultraviolet absorption and fluorescence spectroscopies were employed to obtain the equilibrium constants. In most BDOZs the protonated species were promptly cleaved at the oxazolidine ring fused to the diazepine nucleus, and equilibrated with the original species. A few exceptional compounds required an appreciable time lag for the equilibration. The effects of substituents on the pKa value are discussed from the viewpoint of physical organic chemistry.

  研究了恶唑仑（10-氯-2, 3, 5, 6, 7, 11b-hexahydro-2-methyl-11b-phenylbenzo [6, 7]-1, 4-diazepino [5, 4-b] oxazol-6-one）和 1, 4-苯并二氮杂卓（BDOZ）的 13 种其他衍生物的酸碱平衡反应。研究采用紫外吸收光谱和荧光光谱来获得平衡常数。在大多数 BDOZ 中，质子化的物质会在与二氮杂卓核融合的恶唑烷环上迅速裂解，并与原始物质达到平衡。少数特殊化合物的平衡需要明显的时间差。从物理有机化学的角度讨论了取代基对 pKa 值的影响。
• Kinetics of hydrolysis of oxazolam in aqueous solution.
  作者：MASARU IKEDA、TSUNEJI NAGAI

  DOI：10.1248/cpb.32.1080

  日期：——

  The hydrolysis reaction of oxazolam, a representative of 1, 4-benzodiazepinooxazoles (BDOZ), was investigated kinetically. The reaction product was identified by thin layer chromatography (TLC) and infrared (IR) spectroscopy, and it was concluded that irreversible hydrolytic cleavage took place at the diazepinone nucleus. The rate constant was determined by ultraviolet (UV) spectroscopy. The reaction was a first-order process consisting of two parallel reactions with different reacting species of oxazolam, depending on the pH of the medium. The pH-rate profile obtained for the reaction suggested that the reaction was independent of hydrogen ion concentration in acidic media, while it was catalyzed by hydroxide ion in alkaline media. The nonlinear least-squares fit method was employed to determine the catalytic rate constants involved in the equation describing the pH-rate constant relationship. Activation energies as well as other thermodynamic parameters were obtained in media of pH 2.0 and 8.0, and the values confirmed that different chemical species of oxazolam were involved. The observed effect of buffer concentration indicated that general base catalysis was involved in the reaction of the ionized species of oxazolam. A mechanistic consideration indicated that the rate-determining step may be the nucleophilic attack of a water molecule or hydroxide ion at the 11b-position in the diazepinone nucleus.

  研究了1,4-苯二氮卓噻唑（BDOZ）代表性化合物氧噻唑的水解反应动力学。通过薄层色谱（TLC）和红外光谱（IR）鉴定了反应产物，并得出结论：在二氮杂庚酮核发生了不可逆的水解裂解。通过紫外光谱（UV）确定了反应速率常数。该反应为一阶过程，由两种不同反应物种的平行反应组成，取决于介质的pH值。获得的pH-速率曲线表明，在酸性介质中，反应与氢离子浓度无关，而在碱性介质中则受到氢氧根离子的催化。采用非线性最小二乘拟合方法确定了描述pH-速率常数关系方程中涉及的催化速率常数。在pH为2.0和8.0的介质中获得了活化能和其他热力学参数，数值确认了不同化学物种的氧噻唑参与了反应。观察到的缓冲浓度效应表明，反应中涉及了离子化氧噻唑物种的一般碱催化。机理考量表明，速率决定步骤可能是水分子或氢氧根离子在二氮杂庚酮核的11b位点的亲核攻击。
• Intermediates for the production of tricyclic benzodiazepines
  申请人：Hoffmann-La Roche Inc.

  公开号：US04017531A1

  公开（公告）日：1977-04-12

  Tricyclic benzodiazepine derivatives ("A") bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. A bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. A bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. A are useful as sedative, muscle relaxant and anti-convulsant agents.

  本文描述了三环苯二氮平衍生物（“A”），其在1位具有一个羟基较低烷基取代基，并且在苯二氮平骨架的4和5位之间连接了一个杂环环。杂环环将包含出现在苯二氮平环的4位的氮原子，以及连接到苯二氮平环的5位碳原子上的杂原子，可以是氧原子或氮原子。在存在酸催化剂的情况下，通过用环氧化合物处理相应的4,5-不饱和苯二氮平来形成在新杂环环中具有氧原子的A。通过环化相应的开放化合物来制备在新杂环环中具有氮原子或氧原子的A。A可用作镇静剂、肌肉松弛剂和抗惊厥剂。
• Tricyclic benzodiazepines
  申请人：Hoffmann-La Roche Inc.

  公开号：US03997591A1

  公开（公告）日：1976-12-14

  Tricyclic benzodiazepine derivatives (A) bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. "A" bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. "A" bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. "A" are useful as sedative, muscle relaxant and anti-convulsant agents.

  本文描述了一种三环苯二氮平衍生物（A），其1位带有羟基较低烷基取代基，且杂环环在苯二氮平基团的4和5位之间连接。杂环环将包含出现在苯二氮平环的4位的氮原子以及连接到苯二氮平环的5位碳原子的杂原子，可以是氧原子或氮原子。在新的杂环环中带有氧原子的“A”可以通过在存在酸催化剂的条件下用环氧化合物处理相应的4,5-不饱和苯二氮平制备而成。在新的杂环环中带有氮或氧原子的“A”可以通过相应的开放化合物的环化反应制备而成。这些“A”用作镇静剂、肌肉松弛剂和抗惊厥剂。

表征谱图