2-乙基-2-甲基色满-4-酮 | 73509-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-乙基-2-甲基色满-4-酮
• 英文名称: 2-ethyl-2-methyl-chroman-4-one
• 英文别名: 2-ethyl-2-methylchroman-4-one；2-ethyl-2-methylchromanone；2-ethyl-2-methyl-3H-chromen-4-one
• CAS: 73509-12-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: AHDRYPLIXFKNSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-乙基-2-甲基色满-4-酮 在 氯化亚砜 作用下， 以77%的产率得到(2RS,3RS)-3-chloro-2-ethyl-2-methyl-4-oxochroman-3-sulfenyl chloride
  参考文献：
  名称：

  Cycloadditions with 2,2-Dialkyl-3-thioxochroman-4-one S-Sulfides Including an Unprecedented [3 + 5] Cycloaddition

  摘要：

  We report the facile generation of the chroman-4-one-derived thiosulfines 10 under mild conditions by our well-established nucleophilic "unzipping" of the corresponding acetyl alpha-chloroalkyl disulfides 9 which in turn can be prepared from the corresponding alpha-chloro sulfenyl chlorides 8. Spontaneous partial loss of sulfur from 10, most probably by the disproportionation of 10 to 11 and 12, generates the expectedly reactive beta-oxo thioketones 11 which partly dimerize in a precedented Diels-Alder fashion, to give the 1,3,4-oxadithiins 13, and partly cycloadd to 10 to form the 1,2,4-trithiolanes 14 in a well-precedented fashion. Dimerization of 10 can occur in two competing ways: the precedented nonconcerted [3 + 3] cycloaddition (to give 1,2,4,5-tetrathianes 15) and the unprecedented concerted [3 + 5] addition to give 1,3,4,5,6-oxatetrathiocins 16. In the latter interaction one molecule of 10 behaves as a 1,5-dipole and a second molecule as a 1,3-dipole. In one case (10d) extensive sulfur scrambling takes place with formation of the 1,2,3,4,5,6-hexathiepane 17d. It is remarkable how sensitive the reactions of 10 are to minor variations of the simple alkyl substituents in the 2-position. In addition to the usual spectroscopic characterization all isolated key compounds were subjected to X-ray single-crystal structure determinations.

  DOI：

  10.1021/jo981534+
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 丁酮 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-乙基-2-甲基色满-4-酮
  参考文献：
  名称：

  通过3-重氮杂色-4-酮和烯烃高效合成6-氧杂螺[3.4]辛丹-1-酮

  摘要：

  通过Wolff重排和环加成反应获得具有稠合和螺环含氧刚性骨架结构的螺[2,2-二甲基-苯并呋喃，双环[4.2.0]辛烷] -7'-one。然后通过进一步的Baeyer-Villiger氧化合成Spiro [2,2-二甲基-苯并呋喃，六氢-异苯并呋喃] -7'-one。这两种产品具有特殊的熔融和螺环含氧刚性骨架结构，这是我们小组报告的。

  DOI：

  10.1002/adsc.201701197

文献信息

• Transition metal free regio-selective C–H hydroxylation of chromanones towards the synthesis of hydroxyl-chromanones using PhI(OAc)₂ as the oxidant
  作者：N. Viswanadh、Ganesh S. Ghotekar、Mahesh B. Thoke、R. Velayudham、Aslam C. Shaikh、M. Karthikeyan、M. Muthukrishnan

  DOI：10.1039/c7cc08588e

  日期：——

  The chromanone scaffold is considered as a privileged structure in drug discovery. Herein, we report a highly efficient PhI(OAc)2 mediated regioselective, direct C–H hydroxylation of chromanones. This method offers easy access to substituted 6-hydroxy chromanones in moderate to good isolated yields, thus paving the way for their pharmaceutical studies.

  苯并二氢吡喃酮骨架被认为是药物发现中的一种特权结构。在本文中，我们报道了高效的PhI（OAc）2介导发色团的区域选择性，直接C–H羟基化。这种方法可轻松获得中等至良好分离产率的取代6-羟基苯并二氢呋喃酮，从而为他们的药物研究铺平了道路。
• Synthesis and reactivity of some 4-bromo- 2H-chromenes and 2H-thiochromenes
  作者：Christopher D Gabbutt、David J Hartley、John D Hepworth、B.Mark Heron、Magan Kanjia、M.Moshfiqur Rahman

  DOI：10.1016/s0040-4020(01)86967-2

  日期：1994.2

  synthesis of 4-bromo- 2H-chromenes and 2H-thiochromenes and of 1-bromo-3,4-dihydronaphthalene from the corresponding ketones and PBr3 is described. In some instances, significant quantities of the phosphonic acids (3) are isolated. Conversion of the bromo compounds to the lithio derivatives provides access to a wide range of novel 4-substituted 2H-chromenes and 2H-thiochromenes.

  描述了由相应的酮和PBr 3容易地合成4-溴-2 H-色烯和2 H-硫代色烯以及1-溴-3,4-二氢萘。在某些情况下，分离出大量的膦酸（3）。溴化合物向硫代衍生物的转化提供了广泛的新颖的4-取代的2 H-色烯和2 H-硫代色烯的途径。
• Rhodium‐Catalyzed Annulations of 1,3‐Dienes and Salicylaldehydes/2‐Hydroxybenzyl Alcohols Promoted by 2‐Ethylacrolein
  作者：Hong‐Shuang Li、Yang Xiong、Guozhu Zhang

  DOI：10.1002/adsc.201800796

  日期：2018.11.5

  2‐ethylacrolein‐promoted protocol enables the annulation reactions of 1,3‐dienes with either salicylaldehydes or 2‐hydroxybenzyl alcohols leading to 2‐alkylchroman‐4‐ones with high regioselectivity. This research highlights the use of 2‐ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4‐hydroacylation

  铑催化的2-乙基丙烯醛促进方案可以实现1,3-二烯与水杨醛或2-羟基苄醇的环化反应，从而产生具有高区域选择性的2-烷基苯并吡喃-4-酮。这项研究强调了2-乙基丙烯醛的使用，它可能用作铑中间体的二齿配位的工具。机理研究表明，转化过程是通过1,4-加氢酰化途径进行的，并通过随后的oxo-Michael加成反应获得不饱和线性酮。
• Difluorinative ring expansions of benzo-fused carbocycles and heterocycles are achieved with<i>p</i>-(difluoroiodo)toluene
  作者：Zhensheng Zhao、Avery J. To、Graham K. Murphy

  DOI：10.1039/c9cc08310c

  日期：——

  A chemoselective fluorinative ring expansion has been realized using the hypervalent iodine (HVI) reagent p-TolIF2, which delivers β,β-difluoroalkyl arenes in yields up to 89% and allylic gem-difluorides in yields up to 78%. This rapid reaction exploits the ambiphilic nature of alkenes and allenes, and incorporates both fluorine atoms of the (difluoroiodo)arene in the products. The mechanism involves

  使用高价碘（HVI）试剂p -TolIF 2实现了化学选择性的氟化环扩环，该试剂可提供高达89％的产率的β，β-二氟烷基芳烃和高达78％的烯丙基宝石-二氟化物。这种快速反应利用了烯烃和丙二烯的两亲性质，并将（二氟碘）芳烃的两个氟原子都掺入了产物中。该机制涉及1,2-苯基转移，一步即可提供重要的氟化结构单元，以进行生物活性分子合成。
• Synthesis of New Chromeno[4,3-<i>b</i>]pyrazolo[4,3-<i>e</i>]pyridines Derivatives with Antimicrobial Evaluation
  作者：Farag A. El-Essawy、Abd-Allah. Sh. El-Etrawy

  DOI：10.1002/jhet.1687

  日期：2014.1

  chloro derivatives with hydrazine hydrate afforded dihydrochromeno[4,3‐b]pyrazolo[4,3‐e]pyridines derivatives. Condensation of the dimethyl derivative compound with the aromatic aldehydes gave 8‐Arylideneamino‐6,6‐dimethyl‐10H‐chromeno[4,3‐b]pyrazolo[4,3‐e]pyridine.

  通过2,2-二取代的苯并吡喃-4-酮与芳族化合物的一锅三组分反应获得了一系列2-氧代-2,5-二氢-1H-铬诺[4,3- b ]吡啶衍生物乙醛和2-氰基乙酰胺在无溶剂条件下在氢氧化钠存在下进行。苯并吡啶吡啶衍生物与磷酰氯一起加热，得到相应的氯代衍生物。氯代衍生物与水合肼反应，得到二氢色酚[4,3- b ]吡唑并[4,3- e ]吡啶衍生物。将二甲基衍生物化合物与芳族醛缩合，得到8-亚芳基氨基-6,6-二甲基-10 H-色酚[4,3- b ]吡唑并[4,3- e ]吡啶。