2-methoxy-1-phenyl-1-propanol | 42746-55-4

• 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: 2-methoxy-1-phenyl-1-propanol
• 英文别名: 2-Methoxy-1-phenylpropan-1-ol
• CAS: 42746-55-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: UUBLAHOJUFDSRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  145-147 °C(Press: 70-80 Torr)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-phenyl-1-propanol 在 palladium(II) acetylacetonate 、 ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯 、 甲烷磺酸 、 甲酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以72%的产率得到苯基丙酮
  参考文献：
  名称：

  乙二醇衍生物的串联酸/钯催化还原还原重排。

  摘要：

  在本文中，我们描述了酸/ Pd串联催化的乙二醇衍生物向末端甲酸酯的转化。机理研究表明，在[1,2] -H迁移和氧基离去基团的裂解下，底物发生重排成醛。离开的基团被捕获为其甲酸酯，醛被还原并随后酯化为甲酸酯。磺酸可催化醛的重排，而还原步骤则需要独特的催化剂体系，该体系包含Pd（II）-或Pd（0）-前体，其负载量低至0.75 mol％和a，a'-bis（二叔丁基膦基）-邻二甲苯作为配体。还原步骤利用甲酸作为易于处理的转移还原剂。

  DOI：

  10.1002/chem.202000251
• 作为产物：
  描述：

  2-溴苯丙酮 在 lithium aluminium tetrahydride 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2-methoxy-1-phenyl-1-propanol
  参考文献：
  名称：

  Chelation of 2-substituted 1-lithoxides: structural and energetic factors of relevance to synthetic organic chemistry

  摘要：

  A number of lithium 2-(methylamino)-, 2-(dimethylamino)-, 2-methoxy-, and 2-(isopropylthio)-substituted-1-phenyl-1-propoxides were studied as models for asymmetric synthetic strategies for which lithium chelation between two electronegative atoms has frequently been invoked. The heats of formation of these alkoxides were determined by deprotonating the alcohols with lithium bis(trimethylsilyl)amide in a solution calorimeter. Aggregation numbers for the substituted alcohols and their corresponding lithium alkoxides were obtained with freezing point depression and vapor pressure osmometry in THF, benzene, and dioxane. In several cases, solution structures were obtained through H-1, Li-6, and 2D Li-6-H-1 NOE (HOESY) NMR spectroscopy. Solid-state structures of lithium (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (+)-N-methylpseudoephedrate and (-)-N-methylephedrate (as the benzene solvate) were obtained by X-ray crystallography, and both were found to be present as tetramers in which the dimethylamino nitrogen atoms were coordinated to the lithium cations to form five-membered chelate rings. The lithium alkoxides were either tetramers or hexamers in nonpolar solvents; however, the alkoxides' solution structures were very complex in THF as evidenced by several Li-6 resonances observed in the Li-6 NMR spectra at low temperatures. Intramolecular lithium chelation was found to occur in each alkoxide in dioxane and benzene. The enthalpies of chelational stabilization were estimated by comparing their heats of deprotonation with those of nonchelatable 2-alkyl-substituted analogues. The stabilization enthalpies ranged from 5 to 11 kcal/mol per alkoxide molecule.

  DOI：

  10.1021/ja00016a045

文献信息

• Product Studies and Laser Flash Photolysis on Alkyl Radicals Containing Two Different β-Leaving Groups Are Consonant with the Formation of an Olefin Cation Radical
  作者：Brian C. Bales、John H. Horner、Xianhai Huang、Martin Newcomb、David Crich、Marc M. Greenberg

  DOI：10.1021/ja0042938

  日期：2001.4.1

  hydrogen atom transfer to the oxygen of the olefin cation radical, followed by deprotonation. Laser flash photolysis experiments indicate that reaction between 5 and 1,4-cyclohexadiene occurs with a rate constant of approximately 6 x 10(5) M(-1) s(-1). 2,2-Dimethoxy-1-phenylpropane (18) is observed as a minor product. Laser flash photolysis experiments place an upper limit on methanol trapping of 5

  1-溴-2-甲氧基-1-苯基丙-2-基 (3) 和 2-甲氧基-1-苯基-1-二苯基磷酸丙-2-基 (4) 是在混合物中各自 PTOC 前体的连续光解下生成的乙腈和甲醇。自由基在β-位进行取代基的杂裂断裂以产生烯烃阳离子自由基(5)。Z-2-甲氧基-1-苯基丙烯 (15) 是在 1,4- 环己二烯存在下形成的主要产物，据信是由氢原子转移到烯烃阳离子自由基的氧上，然后去质子化的结果。激光闪光光解实验表明 5 和 1,4-环己二烯之间的反应以大约 6 x 10(5) M(-1) s(-1) 的速率常数发生。观察到 2,2-二甲氧基-1-苯基丙烷 (18) 作为次要产物。激光闪光光解实验在 k <1 x 10(3) M(-1) s(-1) 处将甲醇捕获的上限设置为 5，并且不提供除 5 以外的反应性中间体的形成的任何证据。使用两种含有不同离去基团的 PTOC 前体生成一个共同的烯烃阳离子自由基使
• Competition Between C _α ‐S and C _α ‐C _β Bond Cleavage in β‐Hydroxysulfoxides Cation Radicals Generated by Photoinduced Electron Transfer ^†
  作者：Andrea Lapi、Claudio D'Alfonso、Tiziana Del Giacco、Osvaldo Lanzalunga

  DOI：10.1111/php.13455

  日期：2021.11

  and Cα-Cβ bond cleavage within the corresponding cation radicals. Laser flash photolysis experiments unequivocally established the formation of sulfoxide cation radicals showing their absorption band (λ max ≈ 520 nm) and that of 3-CN-NMQ• (λ max ≈ 390 nm). Steady-state photolysis experiments suggest that, in contrast to what previously observed for alkyl phenyl sulfoxide cation radicals that exclusively

  对一系列 β-羟基亚砜的3-氰基-N-甲基-喹啉鎓光诱导单电子氧化进行了动力学和产物研究，以研究相应的 C α -S 和 C α -C β键断裂之间的竞争。阳离子自由基。激光闪光光解实验明确地确定了亚砜阳离子自由基的形成，显示了它们的吸收带（λ max ≈ 520 nm）和 3-CN-NMQ •（λ max ≈ 390 nm）。稳态光解实验表明，与先前观察到的仅经历 C α的烷基苯基亚砜阳离子自由基相反-S 键断裂，β-羟基的存在使得，在某些情况下，C α -C β断裂具有竞争力。支配这种竞争的因素似乎取决于由两个键断裂形成的片段的相对稳定性。用 -OMe 取代 β-OH 基团并没有显着改变阳离子自由基的反应模式，因此表明观察到的羟基对 C α -C β键断裂的有利影响主要在于其稳定碳正离子的能力在这个分裂上形成。
• Mameli, Gazzetta Chimica Italiana, 1909, vol. 39 II, p. 164
  作者：Mameli

  DOI：——

  日期：——
• Electrooxidation of alken-1-ylarenes in aqueous alcohol solutions
  作者：Yu. N. Ogibin、A. I. Ilovaiskii、G. I. Nikishin

  DOI：10.1007/bf00963506

  日期：1991.10

  In the initial stages of the electrooxidation of alken-l-ylarenes - propenylbenzene (Ia) and 4-propenylanisole (Ib) - in aqueous alcohol solutions, 1,2-dialkoxypropyl-(II), 1-hydroxy-2-alkoxypropyl-(VII), and 1,2-dihydroxypropyl arenes (VIII) are formed. Subsequent rupture of the C-C benzyl bond converts the ethers (II) into benzaldehyde acetals (III) and benzaldehydes (IV), and compounds (VII) and (VIII) into (IV). Benzaldehydes (IV) are also formed from (II) by hydrolysis of the acetals (III) - partly for (IIIa) and completely for (IIIb). Electrolysis of (Ia and Ib) in aqueous alcohol solution leads mainly to their conversion into benzaldehydes (IV).
• Tandem Acid/Pd‐Catalyzed Reductive Rearrangement of Glycol Derivatives
  作者：Tanno A. Schmidt、Benjamin Ciszek、Prasad Kathe、Ivana Fleischer

  DOI：10.1002/chem.202000251

  日期：2020.3.18

  investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2]-H-migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. While the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising

  在本文中，我们描述了酸/ Pd串联催化的乙二醇衍生物向末端甲酸酯的转化。机理研究表明，在[1,2] -H迁移和氧基离去基团的裂解下，底物发生重排成醛。离开的基团被捕获为其甲酸酯，醛被还原并随后酯化为甲酸酯。磺酸可催化醛的重排，而还原步骤则需要独特的催化剂体系，该体系包含Pd（II）-或Pd（0）-前体，其负载量低至0.75 mol％和a，a'-bis（二叔丁基膦基）-邻二甲苯作为配体。还原步骤利用甲酸作为易于处理的转移还原剂。