3-(Benzylamino)-5-methylcyclohex-2-en-1-one | 148278-40-4

• 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: 3-(Benzylamino)-5-methylcyclohex-2-en-1-one
• 英文别名: 3-(benzylamino)-5-methylcyclohex-2-en-1-one
• CAS: 148278-40-4；139932-87-9
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: XAHQYCNXXQPCCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.8±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-溴-1,4-萘醌 、 3-(Benzylamino)-5-methylcyclohex-2-en-1-one 在 copper(ll) bromide potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 144.0h， 生成 5-Benzyl-3-methyl-2,3,4,5-tetrahydro-benzo[b]carbazole-1,6,11-trione
  参考文献：
  名称：

  吉那霉素ABCD环系统的区域选择性合成

  摘要：

  新的溴醌-烯胺环化成功地扩展到了无环烯胺酮，从而产生了新的kinamycin ABC构架6的合成，当应用于环状烯胺酮8a-e时，它们的ABCD环系统也首次合成。用DDQ分别实现化合物4b，d至9a，b的平滑芳构化。

  DOI：

  10.1016/s0040-4039(00)93989-3
• 作为产物：
  描述：

  5-甲基-3-羟基环己-2-烯酮 、 苄胺 以 乙醇 、 苯 为溶剂， 反应 4.0h， 以25%的产率得到3-(Benzylamino)-5-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Anticonvulsant evaluation and mechanism of action of benzylamino enaminones

  摘要：

  The mechanism of anticonvulsant action was evaluated for the benzylamino enaminones. The most potent enaminone in this series was the unsubstituted benzylamine analog (30; methyl 4-benzylamino-6-methyl-2-oxocyclohex-3-en-1-oate) which had an oral effective dose (EDSO) in rats of 27 mg/kg against maximal electroshock seizures, and a concentration 10-fold less than this dose depressed excitatory synaptic transmission, and action potential firing in the rat brain in vitro. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.049

文献信息

• Partially Saturated Indeno[1,2-<i>b</i>]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-<i>N</i>,<i>O</i>-hemiaminals
  作者：Hans-Jörg Hemmerling、Guido Reiss

  DOI：10.1055/s-0028-1087983

  日期：——

  A series of 3-aminocyclohex-2-enones were reacted with indane-1,2,3-trione monohydrate (ninhydrin) yielding 4b,9b-dihydroxyindeno[1,2-b]indoles that were deoxygenated to indeno[1,2-b]indoles.

  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。
• Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors
  作者：Claas Hundsdörfer、Hans-Jörg Hemmerling、Claudia Götz、Frank Totzke、Patrick Bednarski、Marc Le Borgne、Joachim Jose

  DOI：10.1016/j.bmc.2012.02.017

  日期：2012.4

  Herein we describe the synthesis and properties of indeno[1,2-b]indole derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 19 compounds was obtained using a convenient and straightforward synthesis protocol. The compounds were tested for inhibition of human protein kinase CK2, which was recombinantly expressed in Escherichia coli. New inhibitors with IC50 in the micro-

  在这里，我们描述了茚并[1,2- b ]吲哚衍生物的合成及其性质，它们是一类新型的人类蛋白激酶CK2的有效抑制剂。使用方便和直接的合成方案获得了一组19种化合物。测试了化合物对在大肠杆菌中重组表达的人蛋白激酶CK2的抑制作用。鉴定出IC 50在微摩尔和亚微摩尔范围内的新抑制剂。化合物4b（5-异丙基-7,8-二氢茚并[1,2- b ]吲哚-9,10（5 H，6 H）-二酮）抑制人CK2的IC 50浓度为0.11μM，并且没有显着抑制22种其他人类蛋白激酶，表明对CK2具有选择性。显示了化合物4b对ATP的竞争抑制作用，确定的K i为0.06μM。我们的发现表明，茚并[1,2- b ]吲哚是进一步开发和优化人类蛋白激酶CK2抑制剂的有希望的起点。
• Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants
  作者：James E. Foster、Jesse M. Nicholson、Raymond Butcher、James P. Stables、Ivan O. Edafiogho、Angela M. Goodwin、Michael C. Henson、Carlynn A. Smith、K.R. Scott

  DOI：10.1016/s0968-0896(99)00185-6

  日期：1999.11

  A comparison of enaminones from various unsubstituted and p-substituted benzamides to the analogous benzylamines has been undertaken with the aim of elucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocyclohex-3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimethyl-3-N-(benzylamino)-cyclohex-2-en-1-one

  为了阐明抗惊厥活性所必需的基本结构参数，已经进行了将各种未取代和对位取代的苯甲酰胺中的烯胺酮与类似的苄胺进行比较。对4-N-（苄氨基）-6-甲基-2-氧代环己-3-烯-1-酸酯，3a，3-N-（苄基氨基）环己-2-烯-1-酮，3p和5,5-二甲基-3-N-（苄氨基）-环己-2-烯-1-酮，3r表示苄胺具有明显的最大抗电击癫痫发作（MES）活性。对类似苯甲酰胺的评估表明，其抗惊厥活性存在显着差异，这些差异很可能与它们三维结构的差异有关。
• Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition
  作者：Quang Huy To、Yong Rok Lee、Sung Hong Kim

  DOI：10.1007/s00706-012-0762-0

  日期：2012.10

  A simple and efficient method to synthesize a variety of tetrahydroquinolinones was successfully achieved by reacting various beta-enaminones with several alpha,beta-unsaturated aldehydes. This strategy can be viewed as a Bronsted acid-mediated formal [3+3] cycloaddition.
• Anticonvulsant evaluation and mechanism of action of benzylamino enaminones
  作者：Ivan O. Edafiogho、Kethireddy V.V. Ananthalakshmi、Samuel B. Kombian

  DOI：10.1016/j.bmc.2006.03.049

  日期：2006.8

  The mechanism of anticonvulsant action was evaluated for the benzylamino enaminones. The most potent enaminone in this series was the unsubstituted benzylamine analog (30; methyl 4-benzylamino-6-methyl-2-oxocyclohex-3-en-1-oate) which had an oral effective dose (EDSO) in rats of 27 mg/kg against maximal electroshock seizures, and a concentration 10-fold less than this dose depressed excitatory synaptic transmission, and action potential firing in the rat brain in vitro. (c) 2006 Elsevier Ltd. All rights reserved.