(+/-)-2-(2-chlorophenyl)-1,3-oxazolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2-(2-chlorophenyl)-1,3-oxazolidine
• 英文别名: 2-(2-chloro-phenyl)-oxazolidine；2-(2-Chlor-phenyl)-oxazolidin；2-(2-Chlorophenyl)-1,3-oxazolidine
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: UOQYLKLVYVXKMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙烯酮 、 (+/-)-2-(2-chlorophenyl)-1,3-oxazolidine 以 乙酸乙酯 为溶剂， 反应 24.0h， 以91%的产率得到(+/-)-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine
  参考文献：
  名称：

  Effective synthesis and X-ray investigation of (±)-2S-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine

  摘要：

  (±)-2S-2-(2-氯苯基)-3-乙酰基-1,3-噁唑烷的晶体和分子结构通过X射线衍射分析确定。晶体为正交晶系，晶胞参数a = 6.7419(8) Å，b = 10.3797(12) Å，c = 14.9233(18) Å；空间群P212121，Z = 4，ρ计算 = 1.436 g/cm³，组成C11H12ClNO2。氯原子偏离苯环平均平方平面的偏差为−0.010(5) Å。五元噁唑烷环具有信封构型，这是此类化合物的典型特征；环相对于苯片段在C-C键处旋转（二面角为79.7(1)°）。位于2-氯苯片段平面内的C2手性中心的空间结构可以描述为一个具有S构型的sp³杂化碳原子的扭曲四面体。通过对扭转角和氮原子偏离其周围三角平面的分析（偏差为−0.017(3) Å），可以说三取代氮原子倾向于形成金字塔结构。三维晶体结构由C-H...O类型的分子间氢键和氯原子与酰基羰基氧之间的强烈分子间接触3.164(3) Å形成。

  DOI：

  10.1007/s10947-006-0254-3
• 作为产物：
  描述：

  2-氯苯甲醛 、 C.I.酸性橙108 在 molecular sieve 作用下， 以 xylene 为溶剂， 反应 2.0h， 以57%的产率得到(+/-)-2-(2-chlorophenyl)-1,3-oxazolidine
  参考文献：
  名称：

  Effective synthesis and X-ray investigation of (±)-2S-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine

  摘要：

  (±)-2S-2-(2-氯苯基)-3-乙酰基-1,3-噁唑烷的晶体和分子结构通过X射线衍射分析确定。晶体为正交晶系，晶胞参数a = 6.7419(8) Å，b = 10.3797(12) Å，c = 14.9233(18) Å；空间群P212121，Z = 4，ρ计算 = 1.436 g/cm³，组成C11H12ClNO2。氯原子偏离苯环平均平方平面的偏差为−0.010(5) Å。五元噁唑烷环具有信封构型，这是此类化合物的典型特征；环相对于苯片段在C-C键处旋转（二面角为79.7(1)°）。位于2-氯苯片段平面内的C2手性中心的空间结构可以描述为一个具有S构型的sp³杂化碳原子的扭曲四面体。通过对扭转角和氮原子偏离其周围三角平面的分析（偏差为−0.017(3) Å），可以说三取代氮原子倾向于形成金字塔结构。三维晶体结构由C-H...O类型的分子间氢键和氯原子与酰基羰基氧之间的强烈分子间接触3.164(3) Å形成。

  DOI：

  10.1007/s10947-006-0254-3

文献信息

• Design of New Cognition Enhancers:  From Computer Prediction to Synthesis and Biological Evaluation
  作者：Athina A. Geronikaki、John C. Dearden、Dmitrii Filimonov、Irina Galaeva、Taissia L. Garibova、Tatiana Gloriozova、Valentina Krajneva、Alexey Lagunin、Fliur Z. Macaev、Guenadij Molodavkin、Vladimir V. Poroikov、Serghei I. Pogrebnoi、Felix Shepeli、Tatiana A. Voronina、Maria Tsitlakidou、Liudmila Vlad

  DOI：10.1021/jm031086k

  日期：2004.5.1

  To discover new cognition enhancers, a set of virtually designed synthesizable compounds from different chemical series was investigated using two computer-aided approaches. One of the approaches is prediction of biological activity spectra for substances (PASS) and the second is prediction of toxicity, mutagenicity, and carcinogenicity (DEREK). To increase the probability of finding new chemical entities, we investigated a heterogeneous set of highly diverse chemicals including different types of heterocycles: five-membered (thiophenes, thiazoles, imidazoles, oxazoles, pyrroles), six-membered (pyridines, pyrimidines), seven-membered (diazepines, triazepines), fused five+six-membered heterocycles (indoles, benzothiazoles, purines, indolizines, neutral, mesoionic, and cationic azolopyridines). A database including 5494 structures of compounds was created. On the basis of the PASS and DEREK prediction results, eight compounds with the highest probability of cognition-enhancing effect were selected. The cognition-enhancing activity testing showed that all of the selected compounds had a pronounced antiamnesic effect and were found to reduce significantly scopolamine-induced amnesia of passive avoidance reflex (PAR). The action of compounds at doses of 1 and 10 mg/kg caused a statistically significant increase in latent time of reflex and in the number of animals, which did not enter the dark chamber when testing the PAR. Therefore, on the basis of computer prediction, new cognition-enhancing agents were discovered within the chemical series, in which this activity was not known previously.
• Effective synthesis and X-ray investigation of (±)-2S-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine
  作者：F. Z. Makaev、F. G. Shepel、S. T. Malinovskii、M. Gdaniec

  DOI：10.1007/s10947-006-0254-3

  日期：2005.11

  The crystal and molecular structure of (±)-2S-2-(2-chlorophenyl)-3-acetyl-1,3-oxazolidine was determined by X-ray diffraction analysis. Orthorhombic crystal with unit cell parameters a = 6.7419(8) Å, b = 10.3797(12) Å, c = 14.9233(18) Å; space group P212121, Z = 4, ρ calc = 1.436 g/cm3, composition C11H12ClNO2. The deviation of the chlorine atom from the mean square plane of the phenyl cycle is −0.010(5) Å. The five-membered oxazolidine cycle has an envelope conformation, which is typical for this class of compounds; the cycle is rotated at the C-C bond with respect to the phenyl fragment (the dihedral angle is 79.7(1)°). The spatial structure of the C2 chiral center lying in the plane of the 2-chlorophenyl fragment may be described as a distorted tetrahedron with an S configuration of the sp 3 hybridized carbon atom. Analysis of torsion angles and deviation of the nitrogen atom from the surrounding three-angle plane by −0.017(3) Å allows one to speak about a tendency toward a pyramidal structure for the trisubstituted nitrogen atom. The 3D crystal structure is formed by intermolecular hydrogen bonds of C-H...O type and a strong intermolecular contact of 3.164(3) Å between the chlorine atom and the carbonyl oxygen of the acyl group.

  (±)-2S-2-(2-氯苯基)-3-乙酰基-1,3-噁唑烷的晶体和分子结构通过X射线衍射分析确定。晶体为正交晶系，晶胞参数a = 6.7419(8) Å，b = 10.3797(12) Å，c = 14.9233(18) Å；空间群P212121，Z = 4，ρ计算 = 1.436 g/cm³，组成C11H12ClNO2。氯原子偏离苯环平均平方平面的偏差为−0.010(5) Å。五元噁唑烷环具有信封构型，这是此类化合物的典型特征；环相对于苯片段在C-C键处旋转（二面角为79.7(1)°）。位于2-氯苯片段平面内的C2手性中心的空间结构可以描述为一个具有S构型的sp³杂化碳原子的扭曲四面体。通过对扭转角和氮原子偏离其周围三角平面的分析（偏差为−0.017(3) Å），可以说三取代氮原子倾向于形成金字塔结构。三维晶体结构由C-H...O类型的分子间氢键和氯原子与酰基羰基氧之间的强烈分子间接触3.164(3) Å形成。