(E)-3-(4-fluorophenyl)but-2-en-1-ol | 148183-94-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-(4-fluorophenyl)but-2-en-1-ol
• 英文别名: 3-(4-fluorophenyl)but-2-en-1-ol
• CAS: 148183-94-2
• 化学式: C₁₀H₁₁FO
• 分子量: 166.195
• InChiKey: JTSBYSCJEWNJMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-fluorophenyl)but-2-en-1-ol 在 亚甲基蓝 、 氧气 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 3-(4-Fluorophenyl)-2-hydroperoxybut-3-en-1-ol
  参考文献：
  名称：

  Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment

  摘要：

  A new series of bile acid-based trioxanes 23a-d, 24a-d, 25a-d, 26a, 26b, and 26d have been synthesized and assessed for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. The antimalarial activity of these trioxanes showed a strong dependence on the side-chain length; shortening side-chain length lead to increase in activity. The antimalarial activity also showed even stronger dependence on the stereochemistry at C3 and C6 (C21 in Figure 5) of the trioxane moiety. Of the two diastereomers isolated of each of the trioxanes, more polar one was significantly more active than the less polar one. The more polar diastereomer of the trioxanes 26a, 26b, and 26d, were the most active compounds of the series. All these three trioxanes provided 100% protection at 24 mg/kg X 4 days. In this model beta-arteether provided 100% and 20% protection at 48 mg/kg X 4 days and 24 mg/kg X 4 days, respectively.

  DOI：

  10.1021/jm301323k
• 作为产物：
  描述：

  在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(4-fluorophenyl)but-2-en-1-ol
  参考文献：
  名称：

  An In Situ Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols

  摘要：

  An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C-F bond formation and C-H bond cleavage.

  DOI：

  10.1021/ja507468u

文献信息

• Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates
  作者：Jun Sun、Fangcheng He、Zhongyao Wang、Dingwu Pan、Pengcheng Zheng、Chengli Mou、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1039/c8cc03017k

  日期：——

  A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary

  开发了α，β-不饱和醛与α-酮膦酸酯之间的卡宾催化的对映选择性[4 + 2]环加成反应。反应得到具有优异对映选择性的手性2-吡喃基膦酸酯。光学富集的膦酸酯产物带有多个官能团，包括不饱和内酯和膦酸酯部分，这些官能团经常导致独特的生物活性。初步研究表明，我们反应所得的产品具有抗菌作用（X. oryzae pv。oryzae）和抗病毒活性（烟草花叶病毒），可用于植物保护。
• Synthesis and antimalarial activity of novel bicyclic and tricyclic aza-peroxides
  作者：Lalit Yadav、Mohit K. Tiwari、Bharti Rajesh Kumar Shyamlal、Manas Mathur、Ajit K. Swami、Sunil K. Puri、Niraj K. Naikade、Sandeep Chaudhary

  DOI：10.1039/c5ra16781g

  日期：——

  six membered ring compounds. All these compounds were assessed for their in vitro antimalarial activity against Plasmodium falciparum. Compound 9a, 9c and 9f, the most active compound of the series, showed IC50 values of 9.43, 8.83 and 5.63 ng mL−1, respectively which were found to be comparable to that of the antimalarial drug chloroquine (IC50 value 5.2 ng mL−1). Compound 9f, the most active compound

  首次使用1 O 2介导的光氧合方法合成了新颖的双环5a-h和三环9a-h氮杂过氧化物，这是52-71％收率的关键步骤，其中一个氧原子1,2,4-三恶烷环的一部分被一个氮原子取代。该方法简单易行，是访问1,2-二氧杂-4-氮杂六元环化合物的有效方法。对所有这些化合物的体外抗恶性疟原虫的疟疾活性进行了评估。该系列中活性最高的化合物9a，9c和9f的IC 50为结果分别为9.43、8.83和5.63 ng mL -1，与抗疟疾药物氯喹的IC值相当（IC 50值为5.2 ng mL -1）。化合物9f是在体外研究中发现的最具活性的化合物，在筛选其在瑞士小鼠中对多药耐药的约氏疟原虫的体内抗疟活性时，以96 mg kg -1 ×4天的剂量对受感染的小鼠提供40％的保护。通过口头途径。在该试验中，β-蒿甲醚和氯喹在第4天显示出100％的寄生虫血症抑制作用，并分别为受感染的小鼠提供100％和80％的保护作用。
• Visible-light-driven regioselective carbocarboxylation of 1,3-dienes with organic halides and CO₂
  作者：Chunlin Zhou、Xinchao Wang、Lei Yang、Lei Fu、Gang Li

  DOI：10.1039/d2gc01256a

  日期：——

  value-added fine chemicals is an attractive synthesis strategy. Herein, we report an unprecedented visible-light-driven regioselective carbocarboxylation of 1,3-dienes with CO2 using aryl and alkyl halides under mild conditions with low-cost potassium formate (HCOOK) to produce carbon dioxide radical anions as the potent reducing agent for the challenging organic halide reduction. Highly 3,4-regioselective

  利用光将二氧化碳 (CO 2 ) 转化为增值精细化学品是一种有吸引力的合成策略。在此，我们报道了一种前所未有的可见光驱动的 1,3-二烯与 CO 2的区域选择性碳羧化反应。在温和条件下使用芳基卤化物和烷基卤化物以及低成本甲酸钾 (HCOOK) 来产生二氧化碳自由基阴离子，作为具有挑战性的有机卤化物还原的有效还原剂。用 1,1-二芳基取代的 1,3-二烯实现了高度的 3,4-区域选择性碳羧化，而用受阻较小的单芳基取代的 1,3-二烯获得了主要的 1,4-碳羧化产物。该协议提供了一种从容易获得的 1,3-二烯和具有 CO 2的有机卤化物中生产复杂 β、γ-不饱和羧酸的快速方法。
• Intramolecular dehydrogenative amination of alkenes <i>via</i> dual organic photoredox and cobalt catalysis without a hydrogen acceptor
  作者：Wan-Lei Yu、Zi-Gang Ren、Wei Ma、Haixue Zheng、Wangsuo Wu、Peng-Fei Xu

  DOI：10.1039/d2gc02084j

  日期：——

  Direct C–H/N–H dehydrogenative coupling is a promising yet thermodynamically unfavorable transformation in the absence of a sacrificial hydrogen acceptor. Herein, a conceptually novel oxidant-free dehydrogenative amination of alkenes through a synergistic photoredox and cobalt catalysis with H2 evolution has been achieved. With this approach, a wide range of five-membered N-heterocycles were synthesized

  在没有牺牲氢受体的情况下，直接 C-H/N-H 脱氢偶联是一种有前途但在热力学上不利的转变。在此，通过协同光氧化还原和钴催化与H 2释放，实现了概念上新颖的烯烃无氧化剂脱氢胺化。通过这种方法，合成了具有优异原子经济性的多种五元 N-杂环。绿色系统将解决对传统氧化条件敏感的挑战。此外，讨论了该方法的范围和机械细节。
• Stereoselective <i>N</i>-Heterocyclic-Carbene-Catalyzed Formal [4 + 2] Cycloaddition: Access to Chiral Heterocyclic Cyclohexenones
  作者：Ladislav Lóška、Vojtěch Dočekal、Ivana Císařová、Jan Veselý

  DOI：10.1021/acs.orglett.2c04021

  日期：2023.1.13

  alkenes containing a polarized double bond with an azolium-dienolate intermediate generated from α-bromo-α,β-unsaturated aldehydes without external oxidation of the Breslow intermediate. Heterocyclic cyclohexenones were produced in good isolated yields (typically about 90%) with good stereochemical outcomes (in most cases, dr > 20/1, and ee = 70–99%). The synthetic utility of the protocol was exemplified

  本研究报告了一种不对称 NHC 催化的杂环烯烃的正式 [4 + 2] 环加成反应，该杂环烯烃含有极化双键和由 α-溴-α,β-不饱和醛生成的唑鎓-二烯醇中间体，无需 Breslow 中间体的外部氧化。杂环环己烯酮以良好的分离产率（通常约为 90%）和良好的立体化学结果（在大多数情况下，dr > 20/1，并且 ee = 70-99%）产生。该协议的综合效用以杂环烯烃的范围为例。