1-(2-溴-6-甲基苯基)乙酮 | 148517-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-溴-6-甲基苯基)乙酮
• 英文名称: 2-bromo-6-methylacetophenone
• 英文别名: 5-methyl-o-bromoacetophenone；1-(2-bromo-6-methylphenyl)ethanone；1-(2-bromo-6-methylphenyl)ethan-1-one
• CAS: 148517-71-9
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: NVGLKPGDXZAVGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-(2-溴-6-甲基苯基)乙酮 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 以94%的产率得到2-bromo-6-methyl-α-methylbenzyl alcohol
  参考文献：
  名称：

  Intramolecular anodic carbon-carbon bond-forming reactions of oxidized phenol intermediates leading to spirodienones. Structural effects on reactivity and evidence for a phenoxonium ion intermediate

  摘要：

  Anodic oxidation of 4-phenylphenol in methanol leads to 4-methoxy-4-phenylcyclohexa-2,5-dienones whereas anodic oxidation of 4-(2-alkenylphenyl)-phenols leads to spirocyclic 2,5-cyclohexadienones in competition with methanol addition to the 4-position. Using 4-phenylphenol and (4-(2-propenylphenyl)phenol as model systems, the optimum conditions for solvent addition versus carbon-carbon bond formation have been studied. The yield of the anodic cyclization reaction shows a dramatic dependence on olefin structure. Whereas 4-(2-propenylphenyl)phenol gives the spirocyclic 2,5-cyclohexadienone in high yield, 4-(2-vinylphenyl)phenol affords the analogous product in only 16 % yield. This low yield of intramolecular carbon-carbon bond-forming reactions can be markedly improved if the vinyl substituent is forced closer to the 4-position of the phenol by the buttressing effect of a o-methyl group. Coloumetric studies as well as the oxidation chemistry of a (4-hydroxyphenyl)(2-propenylaryl)methane derivative support the involvement of a phenoxonium ion as the intermediate in these carbon-carbon bond-forming reactions. Finally, non-oxidative generation of a phenoxonium ion by reaction of 4-hydroxy-4-(2-propenylphenyl)2,5-cyclohexadieneone with methanesulfonyl chloride/triethylamine leads to spirodienones related to those isolated in the anodic oxidation chemistry. Although a slightly acidic media is critical for obtaining good yields of spirodienones for the propenyl system, anodic oxidation of the trimethylsilyl derivatives of the phenol allows this reaction to be performed in neutral or slightly basic media.

  DOI：

  10.1021/jo00064a017
• 作为产物：
  描述：

  2-溴-6-甲基苯甲酸 在 草酰氯 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 43.0h， 生成 1-(2-溴-6-甲基苯基)乙酮
  参考文献：
  名称：

  Intramolecular anodic carbon-carbon bond-forming reactions of oxidized phenol intermediates leading to spirodienones. Structural effects on reactivity and evidence for a phenoxonium ion intermediate

  摘要：

  Anodic oxidation of 4-phenylphenol in methanol leads to 4-methoxy-4-phenylcyclohexa-2,5-dienones whereas anodic oxidation of 4-(2-alkenylphenyl)-phenols leads to spirocyclic 2,5-cyclohexadienones in competition with methanol addition to the 4-position. Using 4-phenylphenol and (4-(2-propenylphenyl)phenol as model systems, the optimum conditions for solvent addition versus carbon-carbon bond formation have been studied. The yield of the anodic cyclization reaction shows a dramatic dependence on olefin structure. Whereas 4-(2-propenylphenyl)phenol gives the spirocyclic 2,5-cyclohexadienone in high yield, 4-(2-vinylphenyl)phenol affords the analogous product in only 16 % yield. This low yield of intramolecular carbon-carbon bond-forming reactions can be markedly improved if the vinyl substituent is forced closer to the 4-position of the phenol by the buttressing effect of a o-methyl group. Coloumetric studies as well as the oxidation chemistry of a (4-hydroxyphenyl)(2-propenylaryl)methane derivative support the involvement of a phenoxonium ion as the intermediate in these carbon-carbon bond-forming reactions. Finally, non-oxidative generation of a phenoxonium ion by reaction of 4-hydroxy-4-(2-propenylphenyl)2,5-cyclohexadieneone with methanesulfonyl chloride/triethylamine leads to spirodienones related to those isolated in the anodic oxidation chemistry. Although a slightly acidic media is critical for obtaining good yields of spirodienones for the propenyl system, anodic oxidation of the trimethylsilyl derivatives of the phenol allows this reaction to be performed in neutral or slightly basic media.

  DOI：

  10.1021/jo00064a017

文献信息

• Substituted 4-amino-thiazol-2-yl compounds as cyclin-dependent kinase inhibitors
  申请人：Agouron Pharmaceuticals Inc.

  公开号：US06569878B1

  公开（公告）日：2003-05-27

  Pharmaceutical compositions containing effective amounts of CDK-inhibiting diaminothiazole compounds of the following formula (where R1 and R2 are as defined in the specification) or their salts, or prodrugs or active metabolites of such compounds or salts, are useful for treating disorders and diseases such as cancer: In preferred embodiments, R1 and R2 are independently unsubstituted or substituted carbocyclic or heterocyclic aryl ring structures. Compounds where R2 is ortho-substituted aryl are especially potent inhibitors of CDKs such as CDK4.

  含有以下式（其中R1和R2如规范中定义）的CDK抑制二氨基噻唑化合物或其盐、前药或这些化合物或盐的活性代谢物的有效量的药物组合物，对于治疗癌症等疾病和疾病是有用的： 在优选实施例中，R1和R2独立地是未取代或取代的碳环或杂环芳基环结构。其中R2为邻位取代芳基的化合物特别是CDK4的有效抑制剂。
• [EN] INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES<br/>[FR] INHIBITEURS DE RÉPLICATION VIRALE, LEUR PROCÉDÉ DE PRÉPARATION ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BIODIM LAB

  公开号：WO2012140243A1

  公开（公告）日：2012-10-18

  The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.

  本发明涉及化合物，及其在治疗或预防病毒性疾病，包括HIV方面的应用。
• Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes
  作者：Guomin Jiang、Hao Ye、Lei Shi、Hong Dai、Xin-Xing Wu

  DOI：10.1021/acs.orglett.1c03517

  日期：2021.12.17

  The application of a C(vinyl), C(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C(vinyl), C(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl

  由于钯催化中反应性双键的干扰，从含乙烯基底物中应用 C(乙烯基)、C(芳基)-钯环具有挑战性。这封信描述了基于 C（乙烯基）、C（芳基）-钯环的 [4 + 2] 或 [4 + 3] 环化反应，在钯/空气系统下使用 α-氧代羧酸作为插入单元。该反应通过关键的乙烯基 C-H 活化和双脱羧序列进行，以良好的产率区域选择性地形成菲和环庚 [1,2,3-de] 萘。克级合成和合成功能材料分子突出了该协议的合成多功能性。
• Direct Copper-Catalyzed C-3 Arylation of Diphenylphosphine Oxide Indoles
  作者：Shang-Dong Yang、Xiao-Ling Huang、Chong Li、Juan Wang

  DOI：10.1055/a-1633-8792

  日期：2022.11

  We have developed a simple and effective method for the C-3 arylation of phosphorus-containing indole compounds in the presence of CuI under mild conditions. This reaction provides a reliable method for the modification of ligands.

  我们开发了一种简单有效的方法，用于在温和条件下在 CuI 存在下对含磷吲哚化合物进行 C-3 芳基化。该反应为配体的修饰提供了可靠的方法。
• Novel ((3Z,5Z)-3,5-bis(phenylimino)-1,2-dithiolan-4-yl) and 3H-[1,2]dithiolo[3,4-b]quinolin-4(9H)-one heterocycles: an effective and facile green route
  作者：Fangfang Jian、Jian Zheng、Yufeng Li、Jing Wang

  DOI：10.1039/b808949c

  日期：——

  Two new sulfur heterocycle systems containing a 1,2-dithiole group, have been synthesized and characterized by IR, 1H NMR and single crystal X-ray crystallography. Optimum conditions for these closed-ring reactions have been studied and the possible reaction mechanism has been explored. A simple, fast, inexpensive and clean green synthesis route has been described here. The anti-cancer activity of these compounds was evaluated in terms of cell growth inhibition against human liver cancer cells HepG2.

  通过红外光谱、1H NMR 和单晶 X 射线晶体学，合成并表征了两个含有 1,2 二硫代基团的新硫杂环系统。研究了这些闭环反应的最佳条件，并探讨了可能的反应机理。本文描述了一条简单、快速、廉价和清洁的绿色合成路线。根据对人类肝癌细胞 HepG2 的细胞生长抑制作用，对这些化合物的抗癌活性进行了评估。