1-丁基-3-苯基-1-丙醇 | 19969-03-0

• 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-丁基-3-苯基-1-丙醇
• 英文名称: 1-phenylheptan-3-ol
• 英文别名: 1-phenyl-3-heptanol；3-hydroxy-1-phenylheptane
• CAS: 19969-03-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: ROAOZBSINSZYOR-UHFFFAOYSA-N

物化性质

• 沸点：
  136-138 °C(Press: 7 Torr)
• 密度：
  0.9446 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  1-丁基-3-苯基-1-丙醇 在 新戊醇 、 2-硝基苯磺酰肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 various solvent(s) 为溶剂， 以80%的产率得到庚基苯
  参考文献：
  名称：

  Single-Step Process for the Reductive Deoxygenation of Unhindered Alcohols

  摘要：

  DOI：

  10.1021/ja971768v
• 作为产物：
  描述：

  1-苯基庚-1-炔-3-醇 在 4-甲基苯磺酸吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 二氯甲烷 、 甲醇 为溶剂， 反应 26.07h， 以86%的产率得到1-丁基-3-苯基-1-丙醇
  参考文献：
  名称：

  Improved Method for the Diimide Reduction of Multiple Bonds on Solid-Supported Substrates

  摘要：

  A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron-poor olefins, and terminal alkynes were the most easily reduced.

  DOI：

  10.1021/jo0622173

文献信息

• Generation and reactivities of organocerium reagents
  作者：Tsuneo Imamoto、Tetsuo Kusumoto、Masataka Yokoyama

  DOI：10.1039/c39820001042

  日期：——

  Organocerium reagents, prepared in situ by the treatment of organolithium compounds with cerium(III) iodide, exhibit characteristic reactivities toward ketones; at –65 °C, nucleophilic additions give the corresponding tertiary alcohols in excellent yields, while, at 0 °C to ca. room temperature, reductive coupling and/or reduction of the ketones prevail.

  通过用碘化铈（III）处理有机锂化合物而原位制备的有机铈试剂具有对酮的特征性反应性。在-65℃下，亲核加成，得到在良好的产率相应的叔醇，同时，在0℃至约 在室温下，还原偶联和/或酮还原占主导。
• Direct Synthesis of Organic Azides from Alcohols Using 2-Azido-1,3-dimethyl­imidazolinium Hexafluorophosphate
  作者：Mitsuru Kitamura、Tatsuya Koga、Masakazu Yano、Tatsuo Okauchi

  DOI：10.1055/s-0031-1290958

  日期：2012.6

  Direct synthesis of organic azides from alcohols was developed. Azide transfer of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) to alcohols proceeds to give the corresponding azides under mild reaction conditions, which were easily isolated because the byproducts are highly soluble in water.

  开发了由醇直接合成有机叠氮化物。在温和的反应条件下，2-叠氮基-1,3-二甲基咪唑啉鎓六氟磷酸酯 (ADMP) 的叠氮化物转移到醇中，得到相应的叠氮化物，由于副产物高度溶于水，因此很容易分离。
• Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid–Solid (Liquid)–Gas Conditions
  作者：Kwihwan Park、Jing Jiang、Tsuyoshi Yamada、Hironao Sajiki

  DOI：10.1248/cpb.c21-00749

  日期：2021.12.1

  solvent-free oxidation of alcohols, which proceeds efficiently under solid–solid (liquid)–gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the

  开发了一种在固-固（液）-气条件下高效进行的钌碳 (Ru/C) 催化无溶剂氧化醇的方案。在空气或氧气条件下，通过在 10% Ru/C 存在下简单搅拌，各种伯醇和仲醇以中等至优异的分离产率转化为相应的醛和酮。无论底物和试剂是固态还是液态，无溶剂氧化反应都能有效地进行，并且可以应用于克级合成而不会损失反应效率。此外，在五次重复使用循环后，Ru/C 的催化活性得以保持。 全尺寸图像
• Synthesis of Nitrile‐Bearing Quaternary Centers by an Equilibrium‐Driven Transnitrilation and Anion‐Relay Strategy
  作者：Sébastien Alazet、Michael S. West、Purvish Patel、Sophie A. L. Rousseaux

  DOI：10.1002/anie.201903215

  日期：2019.7.22

  preparation of nitrile‐containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non‐toxic sources of CN. Herein, we report that 2‐methyl‐2‐phenylpropanenitrile is an efficient, non‐toxic, electrophilic CN source for

  有趣的是，有效制备含腈基砌块的原因在于它们作为合成中间体的用途以及它们在药物中的普遍性。结果，已经做出了巨大的努力来开发依赖于更安全，无毒的CN来获取这些基序的方法。在此，我们报道2-甲基-2-苯基丙腈是一种有效的，无毒的，亲电子的CN来源，可通过热力学氮化和​​阴离子中继策略合成含腈的季铵盐中心。这种一锅法过程会导致烷基锂试剂的宝石双官能化，从而产生腈产品。
• Fluorination of Secondary and Primary Alcohols by Thermal Decomposition of Electrochemically Generated Alkoxy Triphenylphosphonium Tetrafluoroborates.
  作者：Hatsuo MAEDA、Takashi KOIDE、Sayaka MATSUMOTO、Hidenobu OHMORI

  DOI：10.1248/cpb.44.1480

  日期：——

  Replacement of hydroxyl groups in secondary and primary alcohols (1) with a fluorine atom arising from tetrafluorobote anion has been performed by the electrochemical formation of alkoxy triphenylphosphonium tetrafluoroborarates (2) from 1, followed by their thermal decomposition. The procedure is quite simple, involving : (1) constant-current electrolysis of a mixture of 1, Ph3P, and Ph3PH·BF4 in CH2Cl2 in an undivided cell; (2) refluxing a tetrahydrofuran or dioxane solution of the residue afforded by evaporation of the solvent in vacuo after the electrolysis. Cyclic secondary alcohols such as 3β-hydroxy steroids and 2-adamantanol are transformed into the corresponding fluorides in satisfactory yields when the geometry of the leaving group in 2 is suitable for the substitution or an elimination process for 2 to give an alkene is stereochemically forbidden. The fluorination of steroidal alcohols and 4-phenyl-1-cyclohexanol proceeded with complete inversion, demonstrating that a fluorine atom from the tetrafluoroborate anion attacks from the side opposite to the phosphonium moiety in 2 via an SN2 mechanism rather than as SN1 mechanism. The fluorination of acyclic secondary and primary alcohols was performed by the present method in reasonable yields, although the reaction for the latter required more forcing conditions, such as refluxing in dioxane.

  次级和初级醇(1)中的羟基被四氟硼酸根衍生的氟原子取代，通过电化学形成烷氧基三苯基膦四氟硼酸盐(2)，然后进行热分解来实现。该过程相当简单，包括：(1)在无隔膜电池中对1、Ph3P和Ph3PH·BF4的CH2Cl2混合物进行恒电流电解；(2)将电解后在真空下蒸发溶剂得到的残渣的四氢呋喃或二氧六环溶液回流。当2中的离去基团的构型适合取代或消除过程，且2生成烯烃的立体化学被禁止时，环状次级醇如3β-羟基甾体和2-金刚烷醇可转化为相应的氟化物，产率令人满意。甾醇和4-苯基-1-环己醇的氟化反应进行完全反转，表明四氟硼酸根阴离子中的氟原子通过SN2机制从2中膦部分的对面攻击，而不是SN1机制。通过本方法，无环次级和初级醇的氟化反应在合理产率下进行，尽管后者的反应需要更强烈条件，如在二氧六环中回流。