2,3,5-trimethyl-4-phenyl-furan | 88928-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-trimethyl-4-phenyl-furan
• 英文别名: 2,3,5-Trimethyl-4-phenylfuran；3-Phenyl-2,4,5-trimethylfuran
• CAS: 88928-40-9
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: NPJPJRJKLBQCRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基-2-氧代-2-苯基乙酸乙酯 在 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正戊烷 、 苯 为溶剂， 反应 7.0h， 生成 2,3,5-trimethyl-4-phenyl-furan
  参考文献：
  名称：

  通过羟基乙酸酯合成多取代的呋喃，吡咯和噻吩。

  摘要：

  开发了一种使用合成酸酯制备多取代呋喃，噻吩和吡咯的有效合成方法。通过C2-C3和C3-C4键形成的这种新颖的正式[4 +1]环化过程包括关键步骤：环加成，环化，脱羧和脱水。

  DOI：

  10.1021/ol0705200

文献信息

• Redox-Triggered CC Coupling of Diols and Alkynes: Synthesis of β,γ-Unsaturated α-Hydroxyketones and Furans by Ruthenium-Catalyzed Hydrohydroxyalkylation
  作者：Emma L. McInturff、Khoa D. Nguyen、Michael J. Krische

  DOI：10.1002/anie.201311130

  日期：2014.3.17

  ruthenium‐catalyzed CC coupling of alkynes and vicinal diols to form β,γ‐unsaturated ketones occurs with complete levels of regioselectivity and good to complete control over the alkene geometry. Exposure of the reaction products to substoichiometric quantities of p‐toluenesulfonic acid induces cyclodehydration to form tetrasubstituted furans. These alkyne‐diol hydrohydroxyalkylations contribute to a

  直接钌催化的炔烃和邻位二醇的C - C偶联形成β,γ-不饱和酮，具有完全的区域选择性，并且能够很好地完全控制烯烃的几何结构。将反应产物暴露于亚化学计量的对甲苯磺酸会诱导环脱水形成四取代呋喃。这些炔二醇氢羟烷基化导致了越来越多的合并氧化还原反应事件，绕过了预金属化试剂的使用，从而避免了化学计量的金属副产物。
• Reaction of tributyltin enolates with α-halogeno ketones: a new route to furan derivatives
  作者：Masanori Kosugi、Izumi Takano、Isao Hoshino、Toshihiko Migita

  DOI：10.1039/c39830000989

  日期：——

  The reaction of tributyltin enolates with α-halogeno ketones gave substituted furans which were not derived from the normal cross-coupling products, 1,4-diketones, but were formed instead through addition of the tin enolate to the α-halogeno ketones.

  三丁基锡烯酸酯与α-卤代酮的反应产生了取代的呋喃，该呋喃不是由正常的交叉偶联产物1,4-二酮衍生而来的，而是通过将烯醇锡添加到α-卤代酮中而形成的。
• Hydrogen peroxide oxidation of polysubstituted pyrylium salts: formation of enol esters and furans
  作者：Teodor Silviu Balaban、Monika Hiegemann

  DOI：10.1016/s0040-4020(01)92277-x

  日期：1992.11

  2,4,6-Trialkylsubstituted pyrylium salts 1 have been known lo afford 2-acyl-3,5-dialkyl-furans 2 in moderate yields (30 - 45%). Oxidation of these salts in buffer solutions (pH = 3 - 4.5) increased the yields of acylfurans to 75%. In contrast, tetra- and penta-substituted pyrylium salts are mainly converted into enol esters with a delta-keto group and furans all originating presumably by C-O bond cleavages in a common intermediate. This intermediate may result by a C-O acyl shift as inferred from analogous compounds with deuterium labelling.
• Novel Ruthenium- and Platinum-Catalyzed Sequential Reactions: Synthesis of Tri- and Tetrasubstituted Furans and Pyrroles from Propargylic Alcohols and Ketones
  作者：Yoshiaki Nishibayashi、Masato Yoshikawa、Youichi Inada、Marilyn Daisy Milton、Masanobu Hidai、Sakae Uemura

  DOI：10.1002/anie.200351170

  日期：2003.6.16
• Water-Mediated Catalytic Decarboxylation Enabled Polysubstituted Furans and Allylic Alcohols with Exclusive (<i>E</i>)-Configurations
  作者：Yulian Yang、Linhong Zuo、Kun Wei、Wusheng Guo

  DOI：10.1021/acs.orglett.1c00929

  日期：2021.4.16