(2S*,3R*)-2-phenyl-3-methyl-2,3-dihydrobenzo[b]furan

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (2S*,3R*)-2-phenyl-3-methyl-2,3-dihydrobenzo[b]furan
• 英文别名: cis-3-methyl-2-phenyl-2,3-dihydrobenzofuran；cis-2-phenyl-3-methyl-2,3-dihydrobenzo[b]furan；(2S,3R)-3-methyl-2-phenyl-2,3-dihydro-1-benzofuran
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: BIOKQWRMTXWBKZ-ABAIWWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-乙酰苯基苯甲酸酯 在 palladium on activated charcoal 氢气 、 四氯化钛 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 14.5h， 生成 (2S*,3R*)-2-phenyl-3-methyl-2,3-dihydrobenzo[b]furan
  参考文献：
  名称：

  黄烷酮高价碘氧化机理的新见解

  摘要：

  在硫酸存在下，在原甲酸三甲酯（TMOF）中用碘代二乙酸二苯酯（PIDA）氧化黄烷酮（1）时，由于芳基移位而发生立体有择的环收缩，从而生成反甲基2-芳基-2,3-二氢苯并[ b ]呋喃-3-羧酸盐（4a）为主要产品。已经基于NMR，CD和手性HPLC证据讨论了这种转化的机理。

  DOI：

  10.1016/s0040-4020(02)00360-5

文献信息

• Ruthenium Porphyrin Catalyzed Intramolecular Carbenoid C−H Insertion. Stereoselective Synthesis of Cis-Disubstituted Oxygen and Nitrogen Heterocycles
  作者：Wai-Hung Cheung、Shi-Long Zheng、Wing-Yiu Yu、Guo-Chuan Zhou、Chi-Ming Che

  DOI：10.1021/ol034806q

  日期：2003.7.1

  [reaction: see text] A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C[bond]H insertion is described. Using [Ru(II)(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and beta-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [Ru(II)(D(4)-Por*)(CO)]

  [反应：见正文]描述了钌卟啉催化的立体选择性分子内类胡萝卜素C H键插入。使用[Ru（II）（TTP）（CO）]作为催化剂，芳基甲苯磺酰hydr以良好的收率和显着的顺式选择性（高达99％）转化为2,3-二氢苯并呋喃，2,3-二氢吲哚和β-内酰胺。 。以[Ru（II）（D（4）-Por *）（CO）]为催化剂也可完成2,3-二氢苯并呋喃的对映选择性合成，且ee最高可达96％。
• Synthesis of 2,3-Dihydrobenzofurans by Mn(OAc)₃-Based Oxidative Cycloaddition of 2-Cyclohexenones with Alkenes. Synthesis of (±)-Conocarpan
  作者：Barry B. Snider、Luning Han、Chaoyu Xie

  DOI：10.1021/jo9708506

  日期：1997.10.1

  Oxidative cycloaddition of a 2-cyclohexenone or alpha-tetralone and an alkene with dried Mn(OAc)(3) in benzene at 80-140 degrees C provides a general route to dihydrobenzofurans 15 and dihydronaphthofurans 17. Although the yields are modest, this one-pot reaction provides simple access to these compounds, which have previously been prepared by multistep routes. Oxidative cycloaddition of 2-cyclohexenones with beta-methylstyrenes provides a new route to benzofuranoid neolignans, which was applied to the synthesis of conocarpan (22). The formation of 2-acetoxyhexanedioic acids 27 and 47 from acetoxylation of 2-cyclohexenones in HOAc, but not in benzene, opens up a new class of Mn(OAc)(3) reactions and explains Watt and Demir's discovery that much higher yields of alpha'-acetoxy enones are obtained in benzene than in HOAc.