(E)-4-(naphthalen-2-yl)but-3-en-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4-(naphthalen-2-yl)but-3-en-1-ol
• 英文别名: (E)-4-naphthalen-2-ylbut-3-en-1-ol
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: RXSFFEOOCHQWBM-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-(naphthalen-2-yl)but-3-en-1-ol 在 N-hydroxy-N-[(1R,2R)-2-[hydroxy-[3,3,3-tris[4-(2,4,6-triethylphenyl)phenyl]propanoyl]amino]cyclohexyl]-3,3,3-tris[4-(2,4,6-triethylphenyl)phenyl]propanamide 、 vanadium triisopropoxide oxide 、 过氧化氢异丙苯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以98%的产率得到
  参考文献：
  名称：

  Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides

  摘要：

  The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2 center dot DME and a newly developed C-2-symmetric oxazoline ligand plays a key role in selective ring opening of several 3,4-epoxy alcohols at the C4 position. This general protocol furnishes a new type of enantioenriched 4,4-diaryl alkane which also incorporates an additional 1,3-diol that can be easily transformed to a variety of functional groups. The products are formed with excellent regioselectivity (>99:1), diastereoselectivity (up to 99:1), and enantiopurity (up to >99.9% ee).

  DOI：

  10.1021/acs.orglett.7b02076
• 作为产物：
  描述：

  2,4,6-trimethyl-1-(4-(naphthalen-2-yl)butoxy)pyridin-1-ium 4-methylbenzenesulfonate 在 四(三苯基膦)钯 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以58%的产率得到(E)-4-(naphthalen-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  N-烷氧基吡啶盐的光激发钯引发的远程去饱和

  摘要：

  1,5-氢原子转移 (HAT) 是一种实现非功能化烷烃远程脱饱和的有效策略。在此，我们报告了作为烷氧基自由基前体的N -烷氧基吡啶盐的光诱导远程去饱和反应。机理研究表明，激发的钯络合物和N -烷氧基吡啶盐之间的单个电子转移会引发自由基链过程，导致N -烷氧基吡啶盐去饱和。这种链式机制得到了该反应 (Φ = 82) 量子产率测量的支持。该反应适用于一系列N -烷氧基吡啶盐，包括一些复杂的分子衍生盐。

  DOI：

  10.1021/acs.joc.2c02036

文献信息

• Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols
  作者：Xiao-Yu Lu、Jin-Song Li、Jin-Yu Wang、Shi-Qun Wang、Yue-Ming Li、Yu-Jing Zhu、Ran Zhou、Wen-Jing Ma

  DOI：10.1039/c8ra09048c

  日期：——

  Copper-catalyzed cross-coupling reactions of vinyl epoxide with arylboronates to obtain aryl-substituted homoallylic alcohols are described. The reaction selectivity was different to that of previously reported vinyl epoxide ring-opening reactions using aryl nucleophiles. The reaction proceeded under mild conditions, affording aryl-substituted homoallylic alcohols with high selectivity and in good

  描述了乙烯基环氧化物与芳基硼酸酯的铜催化交叉偶联反应以获得芳基取代的高烯丙醇。该反应选择性与之前报道的使用芳基亲核试剂的乙烯基环氧化物开环反应不同。该反应在温和条件下进行，以高选择性和良好至优异的产率提供芳基取代的高烯丙醇。该反应可以方便地从乙烯基环氧化物获得芳基取代的高烯丙醇
• Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides
  作者：Jonathan L. Kuo、John Hartung、Arthur Han、Jack R. Norton

  DOI：10.1021/ja511883b

  日期：2015.1.28

  hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr(CO)3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous all-carbon radicals. From such radicals it is straightforward to

  过渡金属氢化物通过 H• 转移到烯醇醚生成 α-烷氧基自由基。我们测量了从 CpCr(CO)3H 转移到正丁基乙烯基醚的速率常数，并检查了由这种转移产生的自由基的化学性质。来自适当底物的自由基经历 5-exo 环化，具有比类似的全碳自由基更高的非对映选择性。从这些基团很容易制备取代的四氢呋喃。
• Regioselective Heck arylation of unsaturated alcohols by palladium catalysis in ionic liquid
  作者：Jun Mo、Lijin Xu、Jiwu Ruan、Shifang Liu、Jianliang Xiao

  DOI：10.1039/b608033b

  日期：——

  In contrast to almost all of the known examples of Heck arylation of unsaturated alcohols, which yield predominately β-arylated products, arylation under the Pd-DPPP catalysis in ionic liquid leads preferentially to aryl substitution at the α carbon, providing an easy pathway to this valuable class of olefins.

  与已知的不饱和醇的Heck芳基化反应几乎所有的例子（主要产生β-芳基化产物）不同，在离子液体中，Pd-DPPP催化下的芳基化反应优先导致α碳上的芳基取代，为这一类有价值的烯烃提供了便捷的合成途径。
• Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades
  作者：Huan-Ming Huang、Joseph J. W. McDouall、David J. Procter

  DOI：10.1002/anie.201800667

  日期：2018.4.23

  carbonyls by reductive electron transfer are exploited in carbon–carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the proton source used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea

  通过还原电子转移从脲羰基生成的自由基阴离子被用于碳-碳键的形成。尿素自由基阴离子的新的自由基环化传递复杂的氮杂环，并且根据反应中使用的质子来源，反应路径之间的化学选择性转换可以传递两个杂环双环骨架。已经使用计算研究来研究尿素自由基过程的选择性。此外，涉及脲自由基阴离子的自由基环化级联反应提供了不同寻常的螺环氨基结构。
• Electrochemically Enabled Intramolecular Amino- and Oxysulfonylation of Alkenes with Sodium Sulfinates to Access Sulfonylated Saturated Heterocycles
  作者：Xue-Qing Mou、Liang-Chen Ren、Min Wang、Huan-Huan Zhang、Ang Cai、Kuan-Xin Wan、Shi-Min Zhang、Bao-Dong Cui、Yun Zhang、Yong-Zheng Chen

  DOI：10.1021/acs.joc.3c00015

  日期：2023.3.3

  was developed. Under undivided electrolytic cell conditions, a variety of sulfonylated N-heterocycles and O-heterocycles, such as tetrahydrofurans, tetrahydropyrans, oxepanes, tetrahydropyrroles, piperidines, δ-valerolactones, etc., were efficiently prepared from easily accessible unsaturated alcohols, carboxylic acids, and N-tosyl amines without the need for additional metal or exogenous oxidant.

  开发了一种实用且有效的电化学分子内氨基磺酰化或氧磺酰化内部烯烃，该烯烃配备有侧氮或以氧为中心的亲核试剂与亚磺酸钠。在不分开的电解槽条件下，以易得的不饱和醇、羧酸、和否-tosyl 胺，无需额外的金属或外源氧化剂。稳健的电化学转化具有出色的氧化还原经济性、高非对映选择性和广泛的底物特异性，这为含砜杂环化合物提供了一种通用和实用的途径，并将促进基于这种电合成的相关合成和生物学研究。