(9ci)-3,4-二氢-3-甲基-3-苯基-1H-2-苯并吡喃 | 164731-59-3

• 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: (9ci)-3,4-二氢-3-甲基-3-苯基-1H-2-苯并吡喃
• 中文别名: 1H-2-苯并吡喃，3,4-二氢-3-甲基-3-苯基-（9CI）
• 英文名称: 3,4-dihydro-3-methyl-3-phenyl-1H-2-benzopyran
• 英文别名: 3-Methyl-3-phenyl-3,4-dihydro-1H-2-benzopyran；3-methyl-3-phenyl-1,4-dihydroisochromene
• CAS: 164731-59-3
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: PATHWOCAJARLQU-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±11.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-hydroxymethylphenyl)-2-phenyl-2-propanol 在 磷酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以94%的产率得到(9ci)-3,4-二氢-3-甲基-3-苯基-1H-2-苯并吡喃
  参考文献：
  名称：

  1,2-Di(lithiomethyl)benzene from phthalan: Sequential introduction of two different electrophiles

  摘要：

  The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20 degrees C followed by treatment with electrophiles (D2O, CO;! and carbonyl compounds) at -78 degrees C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g. When the Lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added the corresponding disubstituted compounds 6a-q are prepared. Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k), respectively. Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.

  DOI：

  10.1016/0040-4020(95)00064-f

文献信息

• Intramolecular reactivity of arylcarbenes: 2-(Alkoxymethyl)phenylcarbenes
  作者：Wolfgang Kirmse、Dirk Schnitzler

  DOI：10.1016/0040-4039(94)88323-8

  日期：1994.3

  triplet states contribute to the intramolecular CH insertion reactions of 2- (alkoxymethyl)phenylcarbenes, leading to dihydro-1 H-2-benzopyrans. Competitively, oxygen ylides are generated which eventually give rise to benzocyclobutenes and dihydroisobenzofurans. The radical pair mechanism of the Stevens rearrangement is confirmed by variation of the alkyl groups and by means of chiral substrates.

  单重态和三重态都有助于2-（烷氧基甲基）苯基卡宾的分子内CH插入反应，从而导致二氢-1 H -2-苯并吡喃。竞争地，产生了氧化氧，最终产生了苯并环丁烯和二氢异苯并呋喃。史蒂文斯重排的自由基对机理通过烷基的变化和手性底物的证实。
• 1,2-Di(lithiomethyl)benzene from phthalan: Sequential introduction of two different electrophiles
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1016/0040-4020(95)00064-f

  日期：1995.3

  The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20 degrees C followed by treatment with electrophiles (D2O, CO;! and carbonyl compounds) at -78 degrees C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g. When the Lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added the corresponding disubstituted compounds 6a-q are prepared. Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k), respectively. Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.