1-(3-chlorophenyl)-1,3-dihydroindol-2-one | 83254-84-6

• 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: 1-(3-chlorophenyl)-1,3-dihydroindol-2-one
• 英文别名: 1-(3-Chlorophenyl)oxindole；1-(3-chlorophenyl)indolin-2-one；1-(3-chlorophenyl)-2(1H,3H)-indolone；N-(3-chlorophenyl)-indolin-2-one；1-(3-Chlorophenyl)-indolin-2-one；1-(3-chlorophenyl)-3H-indol-2-one
• CAS: 83254-84-6
• 化学式: C₁₄H₁₀ClNO
• 分子量: 243.692
• InChiKey: HMWMGKFMLJFUJI-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  488.4±44.0 °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：

  1-(3-chlorophenyl)-1,3-dihydroindol-2-one 在 氨 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 3-[1-Amino-eth-(Z)-ylidene]-1-(3-chloro-phenyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  A novel class of "GABAergic" agents: 1-aryl-3-(aminoalkylidene)oxindoles

  摘要：

  Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles. Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)-ethylidene and N-methyl-2-pyrrolidinylidene side chains. The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels. Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid. Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.

  DOI：

  10.1021/jm00122a025
• 作为产物：
  描述：

  邻溴苯乙酸 在 palladium diacetate caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 1-(3-chlorophenyl)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  微波辅助顺序酰胺键形成和分子内酰胺化：快速进入功能化的吲哚。

  摘要：

  已经开发了用于合成N-取代的羟吲哚的通用方法。此两步过程涉及在2-卤代芳酸与各种烷基胺和苯胺之间首先形成微波辅助的酰胺键，然后在水性条件下进行钯催化的分子内酰胺化反应。在烷基胺的情况下，该过程可以一锅法进行，而无需分离中间体酰胺。[结构：见文字]

  DOI：

  10.1021/ol0473804

文献信息

• 4-aryl substituted indolinones
  申请人：Sugen, Inc.

  公开号：US20030069297A1

  公开（公告）日：2003-04-10

  The present invention relates to 4-arylindolinones, as well as pharmaceutical compositions thereof, capable of modulating protein kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation. The present invention also relates to methods for treating protein kinase related disorders.

  本发明涉及4-芳基吲哚酮，以及其药物组合物，能够调节蛋白激酶信号传导，以调节、调节和/或抑制异常细胞增殖。本发明还涉及治疗蛋白激酶相关疾病的方法。
• .alpha.,.alpha.-disubstituted aromatics and heteroaromatics as cognition
  申请人：The DuPont Merck Pharmaceutical Co.

  公开号：US05173489A1

  公开（公告）日：1992-12-22

  Cognitive defeciencies or neurological dysfunction in mammals are treated with .alpha.,.alpha.-disubstituted aromatic or heteroaromatic compounds. The compounds have the formula: ##STR1## or a salt thereof wherein X and Y are taken together to form a saturated or unsaturated carbocyclic or heterocyclic first ring and the shown carbon in said ring is .alpha. to at least one additional aromatic ring or heteroaromatic ring fused to the first ring; one of Het.sup.1 is 2, 3 or 4-pyridyl or 2, 4, or 5-pyrimidinyl and the other is selected from (a) 2, 3, or 4-pyridyl, (b) 2, 4, or 5-pyrimidinyl, (c) 2-pyrazinyl, (d) 3, or 4-pyridazinyl, (e) 3, or 4-pyrazolyl, (f) 2, or 3-tetrahydrofuranyl, and (g) 3-thienyl.

  哺乳动物中的认知缺陷或神经功能障碍可用α，α-二取代芳香或杂芳化合物进行治疗。这些化合物的化学式为：##STR1##或其盐，其中X和Y一起形成饱和或不饱和的碳环或杂环第一环，所示的碳在该环中为至少一个额外的芳香环或杂芳环的α位融合到第一环；Het.sup.1中的一个是2，3或4-吡啶基或2，4或5-嘧啶基，另一个选自(a)2，3或4-吡啶基，(b)2，4或5-嘧啶基，(c)2-吡嗪基，(d)3或4-吡啶嗪基，(e)3或4-吡唑基，(f)2或3-四氢呋喃基，和(g)3-噻吩基。
• 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。
• 3,3-disubstituted indolines
  申请人：E. I. Dupont de Nemours & Company

  公开号：US04760083A1

  公开（公告）日：1988-07-26

  Cognitive deficiencies and/or neurological function deficits and/or mood and/or mental disturbances are treated by the administration of 3,3-disubstituted indolines. The indolines have the formula: ##STR1## wherein: p is 0 or 1; Z is O or S; R is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.8 cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl or ##STR2## V, W, X, and Y independently are H, halo, C.sub.1 -C.sub.3 alkyl, OR.sup.1, NO.sub.2, CF.sub.3, CN or NR.sup.2 R.sup.2 ; R.sup.1 and R.sup.2 independently are H or C.sub.1 -C.sub.3 alkyl; -- .circle.H and -- .circle.H' independently are 6-membered heterocyclic aromatic rings containing at least one nitrogen atom as a part of the ring optionally substituted with one substituent selected from the group C.sub.1 -C.sub.3 alkyl, halo, OR.sup.1 or NR.sup.1 R.sup.2 ; or an N-oxide or pharmaceutically suitable acid addition salt thereof.

  认知缺陷和/或神经功能缺陷和/或情绪和/或精神障碍可通过给予3,3-二取代吲哚烷进行治疗。该吲哚烷的化学式为：##STR1## 其中：p为0或1；Z为O或S；R为C.sub.1-C.sub.10烷基，C.sub.3-C.sub.8环烷基，2-吡啶基，3-吡啶基，4-吡啶基或##STR2## V，W，X和Y独立地为H，卤素，C.sub.1-C.sub.3烷基，OR.sup.1，NO.sub.2，CF.sub.3，CN或NR.sup.2R.sup.2；R.sup.1和R.sup.2独立地为H或C.sub.1-C.sub.3烷基；-- .circle.H和-- .circle.H'独立地为6元杂环芳香环，其中至少有一个氮原子作为环的一部分，可选择地被一种来自群C.sub.1-C.sub.3烷基，卤素，OR.sup.1或NR.sup.1R.sup.2的取代基取代；或其N-氧化物或药学上适宜的酸加合盐。