1-(2,2-二甲氧基丙基)-2-甲氧基苯 | 90177-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,2-二甲氧基丙基)-2-甲氧基苯
• 英文名称: 1-(2-methoxyphenyl)-2,2-dimethoxypropane
• 英文别名: 1-(2,2-Dimethoxypropyl)-2-methoxybenzene
• CAS: 90177-06-3
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SJNWZKNJVCLZSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,2-二甲氧基丙基)-2-甲氧基苯 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 5-hydroxy-3-(2-methoxybenzyl)-5-trifluoromethyl-4,5‑dihydroisoxazole
  参考文献：
  名称：

  An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives

  摘要：

  A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)(2)CH=C(Me)(2), (CH2)(2)Ph, (CH2)(2)-(4-HOC6H4), (CH2)(2)-(4-MeOC6H4), (CH2)(2)CO2Me, (CH2)(3)CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R-1 = H, and R = H and R-1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.

  DOI：

  10.21577/0103-5053.20190160
• 作为产物：
  描述：

  邻甲氧基苯丙酮 、 原甲酸三甲酯 在 对甲苯磺酸 作用下， 生成 1-(2,2-二甲氧基丙基)-2-甲氧基苯
  参考文献：
  名称：

  An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives

  摘要：

  A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)(2)CH=C(Me)(2), (CH2)(2)Ph, (CH2)(2)-(4-HOC6H4), (CH2)(2)-(4-MeOC6H4), (CH2)(2)CO2Me, (CH2)(3)CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R-1 = H, and R = H and R-1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.

  DOI：

  10.21577/0103-5053.20190160

文献信息

• Process for producing phenylacetones
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0101223A2

  公开（公告）日：1984-02-22

  A phenylacetone or its derivative having the general formula (I): wherein X. Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): wherein X, Y and Z are as defined above, with an alkyl nitrite having the general formula (III):wherein R is an aliphatic, aromatic or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned alkyl nitrite in the presence of (a) an alcohol, (b) a palladium catalyst and (c) an optional amine or copper compound to form 1-phemrl-2,2-dialkoxypropane or it derivative having the general formula (IV): wherein X, Y, Z and R are as defined above, followed by hydrolyzing the reaction product.

  具有通式(I)的苯丙酮或其衍生物： 其中 X.Y和Z独立地为氢原子、羟基、卤素原子、硝基、氨基、1至6个碳原子的低级烷基、1至6个碳原子的低级烷氧基或苄氧基，且X、Y和Z的任意两个取代基可与苯环一起形成一个具有5至7个成员（包括1或2个氧原子）的杂环： 其中 X、Y 和 Z 如上定义，与通式（III）的亚硝酸烷基酯反应：其中 R 为脂肪族、芳香族或脂环族饱和或不饱和烃基，在 (a) 水、(b) 醇、(c) 钯催化剂和 (d) 任选胺或铜化合物存在下反应、或在(a)醇、(b)钯催化剂和(c)任选胺或铜化合物存在下，使上述 3-苯基丙烯或其衍生物与上述亚硝酸烷基酯反应，生成通式为(IV)的 1-苯基-2,2-二烷氧基丙烷或其衍生物： 其中 X、Y、Z 和 R 如上定义，然后水解反应产物。
• US4638094A
  申请人：——

  公开号：US4638094A

  公开（公告）日：1987-01-20
• An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives
  作者：Valéria Bareño、Daiane Santos、Leandro Frigo、Debora de Mello、Juliana Malavolta、Rogerio Blanco、Lucas Pizzuti、Darlene Flores、Alex Flores

  DOI：10.21577/0103-5053.20190160

  日期：——

  A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)(2)CH=C(Me)(2), (CH2)(2)Ph, (CH2)(2)-(4-HOC6H4), (CH2)(2)-(4-MeOC6H4), (CH2)(2)CO2Me, (CH2)(3)CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R-1 = H, and R = H and R-1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.