(4-(tert-butyl)phenyl)(furan-2-yl)methanol

• 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: (4-(tert-butyl)phenyl)(furan-2-yl)methanol
• 英文别名: 4-tert-Butylphenyl-(2-furyl)methanol；(4-tert-butylphenyl)-(furan-2-yl)methanol
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: BMKTXXUDACAZTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 (4-(tert-butyl)phenyl)(furan-2-yl)methanol 在 lipoprotein lipase-D₁ 、 C₄₃H₃₅ClO₁₀Ru 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 48.5h， 以91%的产率得到(S)-(4-(tert-butyl)phenyl)(furan-2-yl)methyl acetate
  参考文献：
  名称：

  Dynamic Kinetic Resolution of Diarylmethanols with an Activated Lipoprotein Lipase

  摘要：

  We explored the kinetic resolution of 31 different diarylmethanols with an activated lipoprotein lipase (LPL-D1) which was about 3000-fold more active than its native counterpart in organic solvent. Most of the substrates tested were accepted by LPL-D1 with good to high enantioselectivity in the kinetic resolution. Next, we explored the dynamic kinetic resolutions (DKRs) of these substrates (24 out of 31) using LPL-D1 and a ruthenium-based racemization catalyst in combination, which provided satisfactory yields (71-96%) and high enantiopurities (90-99% cc). As an illustrative example for the synthetic applications of the DKR procedure, we synthesized L-cloperastine, an antitussive drug, from phenyl-(p-trimethylsilylphenyl)methanol via DKR.

  DOI：

  10.1021/cs501629m

文献信息

• A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels–Alder Reaction: Stereoselective Synthesis of Octahydro-1<i>H</i>-cyclopenta[<i>cd</i>]isoindole
  作者：Shaik Gouse、Narra Rajashekar Reddy、Sundarababu Baskaran

  DOI：10.1021/acs.orglett.9b01267

  日期：2019.5.17

  an efficient one-pot method for the construction of an angularly fused 5–6–5 aza-tricyclic framework has been developed in a highly stereoselective manner. This domino reaction is a novel combination of aza-Piancatelli rearrangement and intramolecular Diels–Alder reaction, which readily furnishes hexahydro-2a,5-epoxy-cyclopenta[cd]isoindole adducts, bearing six contiguous stereogenic centers in very

  首次以高度立体选择性的方式开发了一种有效的单锅法，用于构建有角度融合的5-6-5氮杂三环骨架。该多米诺反应是氮杂-Piancatelli重排和分子内Diels-Alder反应的新颖组合，可轻松提供六氢-2a，5-环氧-环戊[ cd ]异吲哚加合物，带有六个连续的立体中心，且收率很高。BBr 3介导的氧杂桥联加合物的裂解导致八氢-1 H-环戊[ cd ]异吲哚的形成，这是gracilamine生物碱的氮杂-三环BCE核心。
• Sequential aza-Piancatelli rearrangement/Friedel–Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives
  作者：B. V. Subba Reddy、Y. Vikram Reddy、Kiran Kumar Singarapu

  DOI：10.1039/c5ob01616a

  日期：——

  2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel–Crafts alkylation with (1H-pyrrol-1-yl)aniline, in the presence of In(OTf)₃ at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds.

  2-呋喃基甲醇经过平滑的氮杂皮安卡特利重排反应，随后在室温下与(1H-吡咯-1-基)苯胺在In(OTf)3存在下经过Friedel-Crafts烷基化反应，得到相应的六氢苯并[b]环戊[f]吡咯[1,2-d][1,4]二氮杂环十一(4aH)-酮骨架。
• Highly Efficient Direct Synthesis of Scaffold 9a,10,12,12a‐Tetrahydrobenzo[ <i>b</i> ]cyclopenta[ <i>f</i> ]pyrrolo[1,2‐ <i>d</i> ][1,4]diazepinone by Using Active Phoshomolybdic Acid
  作者：Yuvaraj P. Sarnikar、Dhanraj O. Biradar、Yogesh D. Mane、Bhimrao C. Khade

  DOI：10.1002/jhet.3500

  日期：2019.3

  2‐(1H‐pyrrol‐1‐yl) aniline has been achieved in the presence of 10 mol% phosphomolybdic acid in CH3CN under reflux to afford the corresponding biologically active 10‐aryl‐9a,10,12,12a‐tetrahydrobenzo[b]cyclopenta[f]pyrrolo[1,2‐d][1,4]diazepin‐11(9H)‐ones in good yields. Broad substrate scope, short reaction times, environmentally benign, and operational simplicity makes this method more attractive.

  呋喃-2-基（苯基）甲醇和2-（1 H-吡咯-1-基）苯胺的多米诺偶联反应是在CH 3 CN中存在10 mol％磷钼酸的条件下进行的，以实现相应的生物活性10-芳基-9a，10,12,12a-四氢苯并[ b ]环戊[ f ]吡咯并[1,2- d ] [1,4]二氮杂ze-11（9 H）-收率良好。广泛的底物范围，短的反应时间，对环境无害以及操作简便性使该方法更具吸引力。
• Dynamic Kinetic Resolution of Diarylmethanols with an Activated Lipoprotein Lipase
  作者：Jusuk Lee、Yeonock Oh、Yoon Kyung Choi、Eunjeong Choi、Kyungwoo Kim、Jaiwook Park、Mahn-Joo Kim

  DOI：10.1021/cs501629m

  日期：2015.2.6

  We explored the kinetic resolution of 31 different diarylmethanols with an activated lipoprotein lipase (LPL-D1) which was about 3000-fold more active than its native counterpart in organic solvent. Most of the substrates tested were accepted by LPL-D1 with good to high enantioselectivity in the kinetic resolution. Next, we explored the dynamic kinetic resolutions (DKRs) of these substrates (24 out of 31) using LPL-D1 and a ruthenium-based racemization catalyst in combination, which provided satisfactory yields (71-96%) and high enantiopurities (90-99% cc). As an illustrative example for the synthetic applications of the DKR procedure, we synthesized L-cloperastine, an antitussive drug, from phenyl-(p-trimethylsilylphenyl)methanol via DKR.