4,6-二甲基-1-苯并呋喃-3(2H)-酮 | 20895-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4,6-二甲基-1-苯并呋喃-3(2H)-酮
• 英文名称: 4,6-dimethylbenzofuran-3(2H)-one
• 英文别名: 4,6-dimethylbenzofuran-3-one；4,6-dimethylcoumaranone；4,6-dimethyl-benzofuran-3-one；4,6-Dimethyl-benzofuran-3-on；4,6-dimethyl-3-benzofuranone；4,6-Dimethylbenzofuran-3(2H)-on；4,6-Dimethyl-3(2H)-benzofuranone；4,6-dimethyl-1-benzofuran-3-one
• CAS: 20895-44-7
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: PRPSHVVAZDXSJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53 °C
• 沸点：
  308.8±42.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4,6-二甲基-1-苯并呋喃-3(2H)-酮 在 1,4-二氧六环 、 乙醚 、 水 、 sodium ethanolate 、 苄基三甲基氢氧化铵 作用下， 生成 2-acetyl-4,6-dimethyl-2-(3-oxo-butyl)-benzofuran-3-one
  参考文献：
  名称：

  607.螺环化合物。第一部分：与3：2'-二氧戊酸相关的化合物的制备

  摘要：

  DOI：

  10.1039/jr9570003112
• 作为产物：
  描述：

  3,5-二甲基溴苯 在 Jones reagent 、 potassium carbonate 、 三氟乙酸 、 copper dichloride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 4,6-二甲基-1-苯并呋喃-3(2H)-酮
  参考文献：
  名称：

  铜（ii）催化的芳基溴化物与脂肪族二醇的C–O偶联：醚，酚和苯并稠合的环醚的合成†

  摘要：

  使用更便宜，更有效且易于去除的铜（II）催化剂，开发了一种高效的铜催化的芳基溴化物与脂肪族二醇之间的C-O交叉偶联反应。使用5 mol％的CuCl 2和3当量的K 2 CO 3将宽范围的芳基溴化物与不同长度的脂肪族二醇偶联在不存在任何其他配体或溶剂的情况下，以良好或优异的收率得到相应的羟烷基芳基醚。在这个新开发的方案中，脂族二醇具有多方面的功能，如偶联反应物，配体和溶剂。所得的羟烷基芳基醚进一步容易地转化成相应的苯酚，为从芳基溴化物得到的苯酚提供了一种有价值的替代方法。此外，已证明它们是用于更高级分子如苯并呋喃和苯并稠合的环醚的有用中间体。

  DOI：

  10.1039/c4ob00649f

文献信息

• Heteroaromatic diphosphines as chiral ligands
  申请人：Italfarmaco Sud S.p.A.

  公开号：US05907045A1

  公开（公告）日：1999-05-25

  Chiral diphosphines constituted by an aromatic pentatomic biheterocyclic system, suitable to act as chiral ligands, complexes between said diphosophines and transition metals, and their utilization as chiral catalysts in sterocontrolled reactions, such as diastereo- and enantioselective reduction reactions. Process for the preparation of said chiral diphosophines and process for the preparation of said complexes and for their utilization as chiral catalysts in sterocontrolled reactions.

  手性双膦配体，由芳香性五元双杂环系统构成，适合作为手性配体，与过渡金属形成配合物，并作为手性催化剂在立体控制反应中应用，如差向异构和对映选择性还原反应。制备此类手性双膦配体的方法，以及制备这些配合物及其作为手性催化剂在立体控制反应中应用的方法。
• A Highly Efficient Synthesis of Rocaglaols by a Novel ?-Arylation of Ketones
  作者：Nicole Diedrichs、Jacques P. Ragot、Kai Thede

  DOI：10.1002/ejoc.200400891

  日期：2005.5

  exhibiting a range of biological activities. A new synthetic method for the α-arylation of ketones allows for the synthesis of previously inaccessible rocaglaol derivatives. The key sequence consists of a previously unreported Suzuki type reaction using brominated silyl enol ethers as substrates followed by deprotection of the arylated silyl enol ethers. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  Rocaglaols 是具有一系列生物活性的天然产物。一种用于酮的 α-芳基化的新合成方法允许合成以前无法获得的 Rocaglaol 衍生物。关键序列由先前未报道的 Suzuki 型反应组成，该反应使用溴化甲硅烷基烯醇醚作为底物，然后对芳基化甲硅烷基烯醇醚进行脱保护。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
• Hatton, Paul M.; Sternhell, Sever, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 935 - 946
  作者：Hatton, Paul M.、Sternhell, Sever

  DOI：——

  日期：——
• The Power of Solvent in Altering the Course of Photorearrangements
  作者：Peter Sebej、Bum Hee Lim、Bong Ser Park、Richard S. Givens、Petr Klan

  DOI：10.1021/ol102887f

  日期：2011.2.18

  A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzoturanones occurs abruptly at low water concentrations (similar to 8%). The surprisingly clean yields suggest that such reactions are synthetically promising.