3,6,-dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one | 30557-66-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,6,-dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one
• 英文别名: 4-oxo-menthofuran；(+/-)-evodone；3,6-dimethyl-6,7-dihydro-5H-benzofuran-4-one；3,6-Dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one；3,6-dimethyl-6,7-dihydro-5H-1-benzofuran-4-one
• CAS: 30557-66-5；120707-14-4
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: SMUXTLISYBPIAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6,-dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one 在 乙醇 、 三氟化硼乙醚 、 镍 作用下， 以 二氯甲烷 为溶剂， 生成 薄荷呋喃
  参考文献：
  名称：

  Aso, Mariko; Sakamoto, Mizue; Urakawa, Narumi, Heterocycles, 1990, vol. 31, # 6, p. 1003 - 1006

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 在 吡啶 、 aluminum oxide 、 sodium periodate 、 Celite 、 silver carbonate 作用下， 以 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 26.0h， 生成 3,6,-dimethyl-6,7-dihydro-1-benzofuran-4(5H)-one
  参考文献：
  名称：

  银（I）/硅藻土介导的1,3-二羰基化合物与乙烯基硫化物的3-加成环化反应的简便策略。第一次全合成α-clausenan

  摘要：

  通过银（I）/塞利特介导的二羰基化合物与乙烯基硫化物的环加成反应，可以实现3-酰基呋喃的有效合成。

  DOI：

  10.1016/s0040-4039(97)01235-5

文献信息

• A strategy to 3-acyl-4-methyl furans. Synthesis of (±)-evodone
  作者：A. Srikrishna、K. Krishnan

  DOI：10.1016/s0040-4039(00)80662-0

  日期：1988.1

  Synthesis of Evodone the radical cyclisation of the bromoacetal to methylene tetrahydrofuran is described.

  描述了Evodone的合成，将溴缩醛自由基环化为亚甲基四氢呋喃。
• Titanium(III) chloride mediated synthesis of furan derivatives: Synthesis of (±)-evodone
  作者：S. K. Mandal、M. Paira、S. C. Roy

  DOI：10.1007/s12039-010-0048-1

  日期：2010.5

  Titanocene(III) chloride (Cp2TiCl) mediated one-pot synthesis of furan derivatives has been accomplished. This radical method has been applied for the synthesis of a furanomonoterpene, evodone. Ti(III) species was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and zinc dust in THF.

  氯化钛新茂（III）（Cp 2 TiCl）介导的一锅合成呋喃衍生物已完成。该自由基方法已被用于呋喃单萜，evodone的合成。由可商购获得的二茂钛二氯化物（Cp 2 TiCl 2）和锌粉在THF中原位制备Ti（III）物种。
• Dipolar cycloaddition of rhodium carbenoids with vinyl esters. Total synthesis of pongamol and lanceolatin B
  作者：Michael C. Pirrung、Yong Rok Lee

  DOI：10.1016/s0040-4039(00)73399-5

  日期：1994.8

  A new method for dipolar cycloaddition of diazocyclohexane-1,3-diones, leading to benzofuran derivatives, has been applied to the total synthesis of natural products from Tephrosia and Pongamia.

  一种重氮偶氮环己烷-1,3-二酮偶极环加成反应的新方法，可产生苯并呋喃衍生物，已被用于全合成来自提弗罗西亚和庞加米的天然产物。
• Extract of Euodia suaveolens Scheff, repellent compositions and use thereof
  申请人：CHARABOT

  公开号：US10258036B2

  公开（公告）日：2019-04-16

  The invention relates to an extract of Euodia suaveolens Scheff. The invention is characterized in that the extract is obtained from the airborne portions of the plant by means of at least one extraction step using an organic or hydro-alcoholic solvent, and in that it comprises evodone at a concentration of between 0.1 and 35% by weight of the total weight of the extract, and in that it has an insect repellent activity. The invention also relates to a repellent composition, characterized in that it comprises, in a cosmetically acceptable medium, evodone at a concentration of between 0.1 and 25% by weight of the total weight of the composition, and to the use of evodone as an active agent for repelling insects, in particular mosquitoes and more particularly the European/Mediterranean mosquitoes of the Aedes aegypti species.

  本发明涉及一种 Euodia suaveolens Scheff 的提取物。本发明的特征在于，该提取物是通过至少一个使用有机溶剂或水醇溶剂的萃取步骤从植物的气载部分获得的，它包含的 evodone 的浓度为提取物总重量的 0.1 至 35%（按重量计），并且它具有驱虫活性。本发明还涉及一种驱虫组合物，其特征在于它在一种化妆品可接受的介质中含有浓度为组合物总重量 0.1 至 25% 的 evodone，并涉及使用 evodone 作为驱虫活性剂，特别是驱蚊，尤其是驱埃及伊蚊类的欧洲/地中海蚊子。
• Total Syntheses of Marine Furanosesquiterpenoids, Tubipofurans
  作者：Akio Ojida、Fumiyo Tanoue、Ken Kanematsu

  DOI：10.1021/jo00099a028

  日期：1994.10

  The first total syntheses of marine furanosesquiterpenoids, tubipofuran (1) and 15-acetoxytubipofuran (2), have been achieved via the common intermediate 3. The syntheses were begun by our newly improved fused 3-methylfuran construction method by the reaction of allenic sulfonium salt with the enolate anion of a cyclic 1,3-diketone. Using this fused furan synthesis, multigram quantities of bicyclic 3-methylfurans were readily obtained in only one step. The cis-fused furanodecalin system was constructed by the regioselective Diels-Alder reaction of benzofuran-quinone 5 and Danishefsky diene 4. The Diels-Alder adduct 9 was transformed into the intermediate 3 by sequential radical deoxygenations of the two hydroxy groups derived from benzofuranquinone 5.

表征谱图