1,5-dimethyl-1,3-dihydroisobenzofuran-4-ol | 1204183-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,5-dimethyl-1,3-dihydroisobenzofuran-4-ol
• 英文别名: 1,5-Dimethyl-1,3-dihydro-2-benzofuran-4-ol；1,5-dimethyl-1,3-dihydro-2-benzofuran-4-ol
• CAS: 1204183-49-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: RWTKRZPUGMOEBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(5-methyl-2-furyl)ethyl propargyl ether 在 triazole 作用下， 以 硝基甲烷 为溶剂， 反应 14.0h， 以90%的产率得到1,5-dimethyl-1,3-dihydroisobenzofuran-4-ol
  参考文献：
  名称：

  1,2,3-Triazole as a Special “X-Factor” in Promoting Hashmi Phenol Synthesis

  摘要：

  P-31 NMR experiments revealed rapid decomposition of the Ph3PAu+TfO- complex in the presence of the furan-yne, which resulted in poor reactivity as reported in the literature. Therefore, Instead of tuning different ligands (PR3), the 1,2,3-triazole was applied as a special X-factor to stabilize the catalyst. The desired phenol products were prepared in excellent yields (1% cat. up to 95% yield) and chemoselectivity (>20:1).

  DOI：

  10.1021/ol902680k

文献信息

• Mechanistic Investigations of a Stable, Highly Active, Extremely Sterically Shielded Molecular Gold Catalyst
  作者：Simone G. Weber、David Zahner、Frank Rominger、Bernd F. Straub

  DOI：10.1002/cctc.201200944

  日期：2013.8

  An N‐heterocyclic carbene gold complex IPr**AuNTf2 has been synthesized, spectroscopically investigated, structurally characterized, and used as a highly active and stable catalyst in the Hashmi phenol synthesis (IPr**=1,3‐di‐p‐tolylimidazol‐2‐ylidene with four di‐tert‐butylbenzhydryl ortho substituents, Tf=trifluoromethansulfonyl). A side reaction comprises an irreversible arene oxide ring opening

  N杂环卡宾金络合物IPr ** AuNTf 2已被合成，光谱研究，结构表征并用作Hashmi苯酚合成中的高活性和稳定催化剂（IPr ** = 1,3- di - p - tolylimidazol带有两个二叔丁基苯甲基邻位的-2-亚烷基取代基，Tf ＝三氟甲磺酰基）。副反应包括不可逆的氧化芳烃开环，随后发生1,2，甲基转移。较高的阳离子金物质平衡浓度，对无活性双核中间体的规避和催化剂分解途径的抑制解释了辅助配体的空间需求的优势。炔烃的甲醇加成-水合反应具有烯基金催化剂静止状态的周转限制质子转移步骤，这由较大的主要动力学同位素效应和炔烃竞争实验所表明。
• 1,2,3-Triazole as a Special “X-Factor” in Promoting Hashmi Phenol Synthesis
  作者：Yunfeng Chen、Wuming Yan、Novruz G. Akhmedov、Xiaodong Shi

  DOI：10.1021/ol902680k

  日期：2010.1.15

  P-31 NMR experiments revealed rapid decomposition of the Ph3PAu+TfO- complex in the presence of the furan-yne, which resulted in poor reactivity as reported in the literature. Therefore, Instead of tuning different ligands (PR3), the 1,2,3-triazole was applied as a special X-factor to stabilize the catalyst. The desired phenol products were prepared in excellent yields (1% cat. up to 95% yield) and chemoselectivity (>20:1).