1-(4-氟苯基)戊-1-醇 | 3913-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氟苯基)戊-1-醇
• 英文名称: 1-(4-fluorophenyl)pentan-1-ol
• 英文别名: 1-<4-Fluorphenyl>-pentanol-(1)；1-<4-Fluorphenyl>-1-hydroxy-pentan；1-(4-fluoro-phenyl)-1-pentanol
• CAS: 3913-55-1
• 化学式: C₁₁H₁₅FO
• 分子量: 182.238
• InChiKey: SGCWRWKHMFTANJ-UHFFFAOYSA-N

物化性质

• 沸点：
  130 °C(Press: 16 Torr)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)戊-1-醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以58%的产率得到苯戊醇
  参考文献：
  名称：

  电子转移诱导的胺类还原有机卤化物†

  摘要：

  通过使用胺作为牺牲氢源，研究了各种有机卤化物的还原。UV光诱导的三乙胺对乙烯基卤化物和芳基卤化物的还原反应顺利进行，得到了相应的还原产物。高温加热也引起了还原，DABCO（1,4-二氮杂双环[2.2.2]辛烷）也用作良好的还原剂。

  DOI：

  10.1039/c8cc02445f
• 作为产物：
  描述：

  1-(4-氟-苯基)-1-戊酮 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 3.5h， 生成 1-(4-氟苯基)戊-1-醇
  参考文献：
  名称：

  Effect of structure on potency and selectivity in 2,6-disubstituted-4-(2-arylethenyl)phenol lipoxygenase inhibitors

  摘要：

  A series of 2,6-disubstituted 4-(2-arylethenyl)phenols with potent human neutrophil 5-lipoxygenase (5-LO) inhibiting activity (IC50S in the 10(-7) M range) and weaker human platelet cyclooxygenase (CO) inhibiting activity (IC50S in the 10(-6) M range) is described. This series evolved from the chemical modification of an antiinflammatory dual CO/5-LO inhibitor, 2,6-di-tert-butyl-4-[2-(3-pyridyl)ethenyl]phenol (BI-L-93 BS). The potency and selectivity for 5-LO inhibition is greatly influenced by the nature of the substituents in the 2- and 6-positions. Other structure-activity relationships that determine relative 5-LO and CO potency are discussed. In vivo activity against antigen-induced leukotriene-mediated bronchoconstriction and cell influx in guinea pigs is presented. Representatives of the series are active when administered at 30 mg/kg ip.

  DOI：

  10.1021/jm00169a010

文献信息

• A novel one-pot synthesis of 2-benzoylpyrroles from benzaldehydes
  作者：Ratnesh Sharma、Mangilal Chouhan、Vipin A. Nair

  DOI：10.1016/j.tetlet.2010.02.054

  日期：2010.4

  We herein report a novel one-pot reaction for benzoylation of pyrrole. The key step in the reaction is generation of di(1H-pyrrol-1-yl)zirconium(IV) chloride complex which reacts with benzaldehydes and methyl benzoates to give 2-benzoylpyrroles as the major product.

  我们在此报告了一种新颖的一锅反应进行吡咯的苯甲酰化。该反应的关键步骤是生成二（1 H-吡咯-1-基）氯化锆（IV）配合物，该配合物与苯甲醛和苯甲酸甲酯反应生成2-苯甲酰基吡咯作为主要产物。
• Direct Transformation of Aryl 2-Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis
  作者：Xianqing Wu、Xiaobin Li、Wenyi Huang、Yun Wang、Hui Xu、Liangzhen Cai、Jingping Qu、Yifeng Chen

  DOI：10.1021/acs.orglett.9b00774

  日期：2019.4.5

  secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with

  通过芳族2-吡啶酯与烷基锌试剂的串联Ni催化的交叉偶联反应，以及Ni-H物种还原的羰基，可以将芳基酯直接转化为仲苄醇。初步的机理研究表明，Ni-H物种是通过Negishi试剂的β-氢化物消除原位生成的。在温和的条件下，具有稳定的官能团耐受性，可通过稳定的镍盐催化该反应。
• Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
  作者：Lei Tao、Xueying Guo、Jie Li、Ruoling Li、Zhenyang Lin、Wanxiang Zhao

  DOI：10.1021/jacs.0c07854

  日期：2020.10.21

  The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes

  已经开发了铑催化的酮与 B2pin2 的脱氧和硼酸化，从而有效地形成烯烃、乙烯基硼酸酯和乙烯基二硼酸酯。这些反应的特点是反应条件温和，底物范围广，官能团兼容性好。机理研究支持酮最初经过 Rh 催化脱氧以通过硼烯醇化物中间体得到烯烃，随后 Rh 催化的烯烃脱氢硼化导致乙烯基硼酸酯和二硼化产物的形成，这也得到 DFT 计算的支持。
• (5,6-Dihydro-1,4-dithiin-2-yl)methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions
  作者：Jan Hullaert、Johan M. Winne

  DOI：10.1002/anie.201606411

  日期：2016.10.10

  instrumental for efficient cycloaddition reactions to take place, thus indicating an attractive strategy for controlling the reactivity of heteroatom‐substituted allyl cations. The formal cycloaddition reaction is highly regio‐ and stereoselective and was also used for a short total synthesis of the natural product cuparene in racemic form through a cycloaddition–hydrodesulfurization sequence.

  通过用质子酸简单处理后，标题杂环醇很容易生成硫取代的烯丙基阳离子，从而促进了一系列共轭烯烃型底物在合成上有用的逐步（3 + 2）环加成反应路径。以这种方式引入烯丙基片段提供了对各种环戊烷支架的快速进入。阳离子前体醇的环状性质被证明有助于有效的环加成反应的发生，因此表明了控制杂原子取代的烯丙基阳离子反应性的一种有吸引力的策略。正式的环加成反应具有很高的区域选择性和立体选择性，还用于通过环加成-加氢脱硫序列进行消旋形式的天然产物铜的短暂全合成。
• Efficient chemoselective addition of Grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran
  作者：Weihui Zhong、Yaotiao Wu、Xingxian Zhang

  DOI：10.3184/030823409x460939

  日期：2009.6

  Compared with tetrahydrofuran (THF) as a solvent for the addition reactions between Grignard reagents and carbonyl compounds 2-methyltetrahydrofuran affords the corresponding adducts in higher yields with higher chemoselectivities. Moreover, 2-methyltetrahydrofuran can be readily recycled and reused, which lowers the cost of the process and makes the reaction greener.

  与作为格氏试剂和羰基化合物之间加成反应的溶剂的四氢呋喃 (THF) 相比，2-甲基四氢呋喃以更高的收率和更高的化学选择性提供相应的加合物。此外，2-甲基四氢呋喃易于回收再利用，降低了工艺成本，使反应更环保。