6-chloro-1-phenylindolin-2-one | 83254-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-chloro-1-phenylindolin-2-one
• 英文别名: 1-phenyl-6-chlorooxindole；1-phenyl-6-chloro-2(1H,3H)-indolone；6-chloro-1-phenyl-2(1H,3H)-indolone；6-chloro-1-phenyl-3H-indol-2-one
• CAS: 83254-83-5
• 化学式: C₁₄H₁₀ClNO
• 分子量: 243.692
• InChiKey: XOSTYPSDUQZJEY-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118.5 °C
• 沸点：
  480.1±45.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-1-phenylindolin-2-one 在 2,4,6-三叔丁基吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 生成 6-chloro-1-phenyl-3-(trifluoromethylsulfonyl)-1H-indol-2-ol
  参考文献：
  名称：

  Regioselective Synthesis of Heteroaryl Triflones by LDA (Lithium Diisopropylamide)-Mediated Anionic Thia-Fries Rearrangement

  摘要：

  Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.

  DOI：

  10.1021/ol300842d
• 作为产物：
  描述：

  N1-(3-氯苯基)-2-氯乙胺 在 三氯化铝 、 铜 、 potassium carbonate 作用下， 反应 2.17h， 生成 6-chloro-1-phenylindolin-2-one
  参考文献：
  名称：

  Mono(m-substituted) chloroacetyldiarylamines in the stoll� reaction

  摘要：

  DOI：

  10.1007/bf00568949

文献信息

• Heteroylidene indolone compounds
  申请人：Pfizer Inc.

  公开号：US04476307A1

  公开（公告）日：1984-10-09

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烯基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症的个体或逆转先前或同时使用的神经阻滞剂药物的副作用方面非常有价值；或者在癫痫的治疗中。更广泛的一类取代的1-苯基-3-(氨基烯基)-2(1H,3H)-吲哚酮，以及1-苯基-3-(2-吡咯烯基)-2(1H,3H)-吲哚酮及其同系物，在焦虑症的治疗中非常有价值。
• Structures and phase transition of three isomers of 1-phenylindolin-2-one derivatives: 6-chloro-1-phenylindolin-2-one, 4-chloro-1-phenylindolin-2-one and 1-(3-chlorophenyl)indolin-2-one
  作者：Bing Wang、Qi Fang

  DOI：10.1107/s2053229618015796

  日期：2018.12.1

  Three 1-phenylindolin-2-one derivatives, namely 6-chloro-1-phenylindolin-2-one (A), 4-chloro-1-phenylindolin-2-one (B) and 1-(3-chlorophenyl)indolin-2-one (C), all C₁₄H₁₀ClNO, have been synthesized and the structures of these compounds at room temperature (A _RT, B _RT and C _RT) and low temperature (A _LT, B _LT and C _LT) have been determined. Crystal A at 295 K (A _RT) crystallized in the monoclinic space group P2₁/c and the phenyl ring of the unique molecule exhibits disorder over two positions. At low temperature, the disorder disappeared and crystal A at 90 K (A _LT) crystallized in the triclinic space group P\overline1} with a doubled unit-cell volume and four molecules in the asymmetric unit. Density functional theory (DFT) calculations revealed a low oscillation barrier (0.24 kcal mol⁻¹) of the phenyl ring of molecule A and the phase transition from the P2₁/c structure to the P\overline1} structure can be interpreted in terms of the freezing out of the two conformations at low temperature. Crystal B retains space group P2₁/c in the temperature range from 100 to 297 K. A kind of obtuse-cell to acute-cell change can be recognized; if the unit cell of B _LT at 100 K is set to be a standard obtuse cell [β = 90.341 (2)°] and the cell is kept untransformed in the course of temperature changing, the cell of B _RT at 297 K was found to be acute [β = 89.288 (2)°]. The molecules in structure C are packed in layers, with C—H...O hydrogen bonds between neighbouring layers.

  合成了三种 1-苯基吲哚啉-2-酮衍生物，即 6-氯-1-苯基吲哚啉-2-酮 (A)、4-氯-1-苯基吲哚啉-2-酮 (B) 和 1-(3-氯苯基)吲哚啉-2-酮 (C)，均为 C14H10ClNO。 RT、B 和 C RT）和低温（A LT、B 和 C LT）进行了测定。晶体 A 在 295 K（A RT）在单斜空间群 P21/c 中结晶，独特分子的苯基环在两个位置上表现出无序。在低温条件下，无序状态消失，90 K 时的晶体 A（A LT）在三菱空间群 P\overline1} 中结晶，单位晶胞体积加倍，不对称单元中有四个分子。密度泛函理论（DFT）计算显示，分子 A 的苯环具有较低的振荡势垒（0.24 kcal mol-1），从 P21/c 结构到 P\overline1} 结构的相变可以用两种构象在低温下冻结来解释。晶体 B 在 100 至 297 K 的温度范围内保持着空间群 P21/c。可以看到一种从钝晶胞到锐晶胞的变化；如果将 B LT 在 100 K 时的单胞被设定为标准钝胞[β = 90.341 (2)°]，并且在温度变化过程中保持单胞不变，则 B RT 在 297 K 时的晶胞为锐角 [β=89.288（2）°]。结构 C 中的分子呈层状排列，相邻层之间存在 C-H...O 氢键。
• Method of treating anxiety and depression with
  申请人：Pfizer Inc.

  公开号：US04977178A1

  公开（公告）日：1990-12-11

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经阻滞剂药物的副作用方面非常有价值；或在治疗癫痫方面也非常有价值。更广泛的一类取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，以及1-苯基-3-(2-吡咯烷亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面也非常有价值。
• 1-phenyl-2(1H,3H)-indolone psycho-therapeutic agents
  申请人：Pfizer Inc.

  公开号：US04861880A1

  公开（公告）日：1989-08-29

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经类药物的副作用，或治疗癫痫方面具有价值。更广泛的一类取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，连同1-苯基-3-(2-吡咯烷基亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面具有价值。
• 1-Phenyl-2(1H,3H)-indolone psychotherapeutic agents
  申请人：Pfizer Inc.

  公开号：US04879391A1

  公开（公告）日：1989-11-07

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidiene-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮是高效的GABA能药物，在治疗患有精神分裂症或逆转先前或同时给予的神经类药物副作用方面非常有价值；或在治疗癫痫方面也有用。更广泛的取代的1-苯基-3-(氨基烷基亚甲基)-2(1H,3H)-吲哚酮，连同1-苯基-3-(2-吡咯烷基亚甲基)-2(1H,3H)-吲哚酮及其同系物，在治疗焦虑方面也很有价值。