4,4-dimethylchroman-2-one | 29598-22-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 4,4-dimethylchroman-2-one
• 英文别名: 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran-2-one；4,4-dimethyl-2-oxo-chroman；2H-1-Benzopyran-2-one, 3,4-dihydro-4,4-dimethyl-；4,4-dimethyl-3H-chromen-2-one
• CAS: 29598-22-9
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: ZBSFDCKGUFSQLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-dimethylchroman-2-one 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 15-冠醚-5 、 四氯化锡 、 sodium hydride 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二硫化碳 、 乙醇 为溶剂， 反应 22.58h， 生成 p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)propenyl]benzoic acid
  参考文献：
  名称：

  Conformationally restricted retinoids

  摘要：

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.

  DOI：

  10.1021/jm00377a022
• 作为产物：
  描述：

  1-溴-2-叔丁基苯 在 palladium(II) trifluoroacetate 、 [1,3-bis(2,4,6-trimethylphenyl)-4,5-dimethyl]imidazolium chloride 、 间氯过氧苯甲酸 、 cesium pivalate 作用下， 以 二氯甲烷 、 乙基苯 为溶剂， 20.0~140.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 4,4-dimethylchroman-2-one
  参考文献：
  名称：

  NHC Ligand-Enabled, Palladium-Catalyzed Non-Directed C(sp³)–H Carbonylation To Access Indanone Cores

  摘要：

  A palladium-catalyzed C(sp(3))-H carbonylation of alkylated aryl triflates or bromides under 1 atm of CO has been developed, in which no directing group or oxidant was required. The essence of this reaction is the combination of appropriate NHC ligands with palladium to facilitate the formation of the five-membered cyclopalladium intermediate. Mechanism studies suggest that the insertion of carbon monoxide into two five-membered cyclopalladium species generated via palladium migration might be the crucial step for this transformation. This method offers an efficient solution for expedient construction of indanone cores, which are valuable synthons and pharmacophores ubiquitously found in numerous natural products.

  DOI：

  10.1021/acscatal.9b03426

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR OCULAR DELIVERY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR ADMINISTRATION OCULAIRE
  申请人：GRAYBUG VISION INC

  公开号：WO2020069353A1

  公开（公告）日：2020-04-02

  The present invention provides new prodrags of Sunitinib, Brinzolamide, and Dorzolamide and compositions to treat medical disorders, for example glaucoma, a disorder or abnormality related to an increase in intraocular pressure (TOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy.

  本发明提供了新的Sunitinib、Brinzolamide和Dorzolamide的前药，以及用于治疗医学疾病的组合物，例如青光眼、与眼内压增高有关的疾病或异常（TOP）、需要神经保护的疾病、年龄相关性黄斑变性或糖尿病视网膜病变。
• MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
  申请人：Hoveyda Hamid

  公开号：US20080194672A1

  公开（公告）日：2008-08-14

  The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，可以作为生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、骨骼疾病、遗传疾病、过度增生性疾病和炎症性疾病。
• Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones
  作者：Kevin Meraz、Krishna Kumar Gnanasekaran、Rup Thing、Richard A. Bunce

  DOI：10.1016/j.tetlet.2016.10.005

  日期：2016.11

  An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20 mol % bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields

  描述了一种有效的串联反应方法，该方法使用20摩尔％的三氟甲磺酸铋（III）在沸腾的甲苯中，由富含电子的苯酚和3,3-二甲基丙烯酸或反式巴豆酸制备4-苯并二氢呋喃。在相同条件下，由这些酸各自的相应芳基酯也可以成功地进行反应。该程序易于执行，色谱分离后产品的收率可达25-90％。包括多种底物（每种酸14种底物）以帮助定义过程的范围。报告了其他实验，这些实验证实了事件的顺序涉及（1）酯化，（2）薯条重排和（3）oxa-Michael环闭合。
• On the synthesis of substituted 2,2-dimethyl1-4-chromanones and related compounds
  作者：Péter Sebök、József Jekö、Tibor Timár、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4039(00)78859-9

  日期：1992.5

  A systematic study of the reaction of a series of monosubstituted phenols 3 and 3-methylbut-2-enoic acid 4 in phosphorus oxychloride/zinc chloride revealed that the formation of 4-chromanones was strongly infuenced by the substituents and their position on the aromatic ring of the starting phenols.

  对一系列单取代的酚3和3-甲基丁-2-烯酸4在三氯氧磷/氯化锌中反应的系统研究表明，取代基及其在芳香环上的位置强烈影响了4-色酮的形成。起始酚。
• Design, Synthesis, and Cellular Uptake of Oligonucleotides Bearing Glutathione-Labile Protecting Groups
  作者：Hisao Saneyoshi、Takayuki Ohta、Yuki Hiyoshi、Takeo Saneyoshi、Akira Ono

  DOI：10.1021/acs.orglett.8b03501

  日期：2019.2.15

  Glutathione-labile protecting groups for phosphodiester moieties in oligonucleotides were designed, synthesized, and incorporated into oligonucleotides. The protecting groups on the phosphodiester moieties were cleaved in a buffer containing 10 mM glutathione, which was used as a model of intracellular fluid. Cellular uptake of oligonucleotides bearing glutathione-labile protecting groups was strongly affected

  设计，合成并合成寡核苷酸中对寡核苷酸中的磷酸二酯部分的谷胱甘肽不稳定的保护基。在含有10mM谷胱甘肽的缓冲液中裂解磷酸二酯部分上的保护基，该缓冲液用作细胞内液的模型。带有谷胱甘肽不稳定的保护基的寡核苷酸的细胞摄取受到保护基团的位置和数量的强烈影响。