5-phenyl-3-phenylaminocyclohex-2-en-1-one | 36646-79-4

• 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: 5-phenyl-3-phenylaminocyclohex-2-en-1-one
• 英文别名: 5-phenyl-3-(phenylamino)cyclohex-2-enone；3-anilino-5-phenyl-cyclohex-2-enone；1-Phenyl-cyclohexandion-(3.5)-monoanil；3-Anilino-5-phenyl-cyclohex-2-enon；Phenyldihydroresorcin-monoanil；3-Anilino-5-phenylcyclohex-2-en-1-on；5-Phenyl-3-(phenylamino)cyclohex-2-EN-1-one；3-anilino-5-phenylcyclohex-2-en-1-one
• CAS: 36646-79-4
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: TWQANWHARNYQGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-phenylaminocyclohex-2-en-1-one 在 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到3-Anilino-2-iodo-5-phenylcyclohex-2-en-1-one
  参考文献：
  名称：

  α-Iodination of enaminones using the modified Johnson's procedure: the use of I2 and Et3N

  摘要：

  Facile synthesis of alpha-iodo enaminones 2 was carried out by the use of iodine and triethylamine in methylene chloride in short time in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01518-1
• 作为产物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 苯胺 以 苯 为溶剂， 反应 3.0h， 生成 5-phenyl-3-phenylaminocyclohex-2-en-1-one
  参考文献：
  名称：

  Partially Saturated Indeno[1,2-b]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-N,O-hemiaminals

  摘要：

  一系列3-氨基环己烯-2-酮与单水合的吡喃-1,2,3-三酮（呋喃啉）反应，生成4b,9b-二羟基吲哚[1,2-b]吲哚，其后经脱氧反应转化为吲哚[1,2-b]吲哚。

  DOI：

  10.1055/s-0028-1087983

文献信息

• Cyclization of Cyanoethylated Ketones as a Route to 6-Substituted Indole Derivatives
  作者：Jan Bergman、Birgitta Stensland

  DOI：10.1002/jhet.2048

  日期：2014.1

  δ‐Cyanoketones are quickly cyclized with KOtBu to 3‐aminocyclohex‐2‐enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3‐amino‐6,6‐dimethylcyclohex‐2‐enone gave 3‐chloro‐6,6‐dimethyl‐2,5,6,7‐tetrahydroindole‐2,5‐dione, whose structure was corroborated by X‐ray crystallography, whereas the corresponding molecule without the blocking gem‐dimethyl groups

  δ-氰基酮可通过KOtBu快速环化成3-氨基环己-2-烯酮衍生物，当用草酰氯处理时，它们会生成取代的吲哚。因此，3-氨基-6,6-二甲基环己-2-烯酮产生了3-氯-6,6-二甲基-2,5,6,7-四氢吲哚-2,5-二酮，其结构得到了X射线的证实。晶体学，而没有封闭的二甲基-二甲基基团的相应分子3-氨基环己-2-烯酮通过氢转移得到6-氯-3-羟基羟吲哚。
• An Efficient Synthesis of Pyrroline-Fused Acridine Derivatives Catalyzed by Silica Sulfuric Acid
  作者：Ming-Hua Hu、Wei Lin、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2023

  日期：2014.8

  A simple and efficient synthesis of pyrrolo[2,3,4-kl]acridine-1-one derivatives via the cascade reaction of isatins with enaminones catalyzed by silica sulfuric acid (SSA) has been established. In this reactions, SSA shows a highly catalytic nature: easy to handle procedure, short reaction time, recycle exploitation, insensitivity to air and moisture, and excellent isolated yields. The catalyst could

  已经建立了一种简单高效的合成方法，该方法通过靛红与二氧化硅硫酸（SSA）催化的烯胺酮的级联反应合成吡咯并[ 2,3,4- kl ] ac啶-1-酮衍生物。在此反应中，SSA具有高度催化性：易于操作，反应时间短，可循环利用，对空气和湿气不敏感以及出色的分离收率。催化剂可以循环至少五次。
• Microwave-Assisted Improved Synthesis of Pyrrolo[2,3,4-kl]acridine and Dihydropyrrolo[2,3,4-kl]acridine Derivatives Catalyzed by Silica Sulfuric Acid
  作者：Chengpao Cao、Changliang Xu、Wei Lin、Xuemei Li、Minghua Hu、Juxian Wang、Zhibin Huang、Daqing Shi、Yucheng Wang

  DOI：10.3390/molecules18021613

  日期：——

  An improved synthesis of multifunctionalized pyrrolo[2,3,4-kl]acridine derivatives with different substituted patterns using silica sulfuric acid (SSA) as a heterogeneous catalyst under microwave irradiation conditions was developed. The reaction could be conducted by using readily available and inexpensive substrates within short periods of 12–15 min. under microwave irradiation. Compared with the

  开发了使用二氧化硅硫酸 (SSA) 作为非均相催化剂在微波辐射条件下合成具有不同取代模式的多功能吡咯并 [2,3,4-kl] 吖啶衍生物的改进方法。该反应可以通过使用容易获得且价格低廉的底物在 12-15 分钟的短时间内在微波辐射下进行。与传统方法相比，该方法的显着优点是反应条件温和、操作简单、产率高、反应时间短、过程环保。
• Domino Constructions of Pentacyclic Indeno[2,1-c]quinolines and Pyrano[4,3-b]oxepines by [4+1]/[3+2+1]/[5+1] and [4+3] Multiple Cyclizations
  作者：Bo Jiang、Bao-Ming Feng、Shu-Liang Wang、Shu-Jiang Tu、Guigen Li

  DOI：10.1002/chem.201201109

  日期：2012.8.6

  New three‐component domino reactions have been discovered. The reactions are easy to perform (see scheme; MW=microwave irradiation) and proceed with fast rates, which makes work‐up convenient. Most of the multiple stereocenters and the geometry are controlled well. The stereochemistry has been unequivocally determined by X‐ray structural analysis.

  发现了新的三组分多米诺骨牌反应。该反应易于进行（参见方案；MW=微波辐射）并且进行速度快，这使得后处理变得方便。大多数多个立构中心和几何形状都控制得很好。立体化学已通过 X 射线结构分析明确确定。
• Vorlaender, Justus Liebigs Annalen der Chemie, 1897, vol. 294, p. 284
  作者：Vorlaender

  DOI：——

  日期：——