1-(2-苄氧基苯基)-乙醇 | 94001-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2-苄氧基苯基)-乙醇
• 英文名称: 1-(2-benzyloxyphenyl)-ethanol
• 英文别名: 1-(2-benzyloxyphenyl)-1-ethanol；α-(o-Benzyloxy-phenyl)-aethylalkohol；1-(2-Benzyloxy-phenyl)-aethanol；1-(2-(Benzyloxy)phenyl)ethanol；1-(2-phenylmethoxyphenyl)ethanol
• CAS: 94001-66-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: ZCLOSPAJWAFSDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-(2-苄氧基苯基)-乙醇 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 对甲苯磺酸 、 calcium chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 3-methyl-3H-benzofuran-2-one
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027
• 作为产物：
  描述：

  2-苄氧基苯乙酮 在 potassium tert-butylate 、 氢气 、 C₃₉H₆₆FeK₂N₅O₁₀P₂ 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、2.0 MPa 条件下， 以99 %的产率得到1-(2-苄氧基苯基)-乙醇
  参考文献：
  名称：

  选择性铁(I)加氢催化剂

  摘要：

  铁是地壳中最丰富的过渡金属，了解其在催化等关键技术中的功能非常重要。我们在这里报告一种铁（I）加氢催化剂。我们的催化剂通过异解键断裂活化氢，形成一氢化物，并通过双金属途径（钾辅助氢化物转移）氢化极性双键。观察到的机制似乎排除了氧化加成和还原消除途径，从而允许耐受许多氢化敏感的官能团，如 C=O 键氢化所证明的那样。

  DOI：

  10.1021/jacs.4c07959

文献信息

• Iridium-Catalyzed Arene <i>Ortho</i>-Silylation by Formal Hydroxyl-Directed C−H Activation
  作者：Eric M. Simmons、John F. Hartwig

  DOI：10.1021/ja1086547

  日期：2010.12.8

  the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C-H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80-100 °C in the presence of norbornene as a hydrogen acceptor

  已开发出芳基酮、苯甲醛和苯甲醇衍生物的邻甲硅烷化策略，其中羟基正式作为 Ir 催化芳烃 CH 键活化的指导元素。从羰基化合物或醇一锅生成（氢化）甲硅烷基醚，然后在降冰片烯作为氢受体和 1 mol % [Ir(cod)OMe ]2 和 1,10-菲咯啉作为催化剂形成苯并恶唑。通过 Tamao-Fleming 氧化或 Hiyama 交叉偶联转化为苯酚或联芳基衍生物证明了苯并恶唑产品的合成效用。CH 甲硅烷基化产物的这两种转化都利用系统中的 Si-O 键，并通过用氢氧化物活化甲硅烷基部分来进行，
• Design, synthesis and biological evaluation of novel ring-opened cromakalim analogues with relaxant effects on vascular and respiratory smooth muscles and as stimulators of elastin synthesis
  作者：Mourad Bouhedja、Basile Peres、Wassim Fhayli、Zeinab Ghandour、Ahcène Boumendjel、Gilles Faury、Smail Khelili

  DOI：10.1016/j.ejmech.2017.12.071

  日期：2018.1

  vascular smooth muscle cells showed a strong stimulating effect on elastin synthesis, especially compound B16, which was more active at 20 μM than diazoxide, a reference ATP-sensitive potassium channel activator. Taken together, our results show that the N-methylation of the sulfonylurea moieties of ring-opened cromakalim analogues led to new compounds blocking calcium-gated channels, which had a major

  合成了两个新的含cromakalim的含磺酰脲部分的开环类似物系列（A系列：带有N-未甲基化的磺酰脲，B系列：带有N-甲基化的磺酰脲），并作为血管和呼吸道平滑肌（大鼠主动脉和气管，分别）。离体生物学评估表明，活性最高的化合物（系列B）对内皮完整的主动脉环和气管表现出显着的血管舒张活性。大多数B系列化合物的血管舒张活性（EC 50  <22μM）比参考化合物二氮嗪（EC 50）高 = 24μM）。有趣的是，与参考化合物克罗马卡林（EC 50  = 124μM），特别是化合物B4，B7和B16（EC 50  <10μM）相比，几种B系列测试化合物在气管上也表现出更强的松弛作用。与此相反，系列甲衍生物是在主动脉环差的活性（EC 50  > 57μM所有，并且EC 50  > 200μM为其中大部分），但它们中的一些显示出了一个有趣的放宽对气管（即作用A15和A33，EC 50  = 30μM）。
• DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride
  作者：Qiang Wang、Jian Xu、Zhou-Qing Xu、Ji-Dan Yan

  DOI：10.1007/s11164-012-0738-z

  日期：2013.5

  N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as

  N-苯基苯甲酰氯已被证明是由二甲亚砜（DMSO）催化的高效氯化试剂，可将醇转化为相应的氯化物。反应条件温和，并且大多数底物给出令人满意的产率。使用旋光性苯醇证明了氯化的构型转化。在不降低氯化效率的情况下，DMSO的量可以低至0.001当量。提出了合理的反应机理，并通过实验证明。该反应在伯苄醇，仲苄醇和未活化的脂族醇中是立体选择性的，并且可能是化学选择性的。
• Unexpected Z-stereoselectivity in the Ramberg–Bäcklund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus
  作者：Jonathan S. Foot、Gerard M. P. Giblin、A. C. Whitwood、R. J. K. Taylor

  DOI：10.1039/b418426b

  日期：——

  With certain substituent patterns, benzyl benzyl sulfone systems have been found to give unexpectedly high Z-stereoselectivity (up to E:Z = 1:16) in the Meyers variant of the Ramberg-Backlund reaction. A range of sulfones, bearing various aryl substituents, were explored to rationalize this unprecedented selectivity for Z-stilbene systems. This high level of double bond stereocontrol has also been

  在某些取代基模式下，已发现在Ramberg-Backlund反应的Meyers变体中，苄基苄基砜系统具有出乎意料的高Z-立体选择性（最高E：Z = 1:16）。研究了一系列带有各种芳基取代基的砜，以合理化这种对Z-二苯乙烯体系的前所未有的选择性。这种高水平的双键立体控制也已用于整合素抑制素核的合成，这是两种具有高生物活性的抗HIV化合物的核心。
• Heterogeneous manganese-oxide-catalyzed successive cleavage and functionalization of alcohols to access amides and nitriles
  作者：Peipei He、Bo Chen、Liang Huang、Xixi Liu、Jingzhong Qin、Zehui Zhang、Wen Dai

  DOI：10.1016/j.chempr.2022.02.021

  日期：2022.7

  manganese-oxide-catalyzed successive cleavage and amidation of C–C bonds in alcohols. A wide range of primary and secondary alcohols, 1,2-diols, and even β-O-4 and β-1 lignin model compounds can undergo C–C bond cleavage smoothly to deliver one- or multiple-carbon shorter amides. Moreover, a slight modification of reaction conditions allows for the cleavage and cyanation of alcohols to access sterically hindered nitriles

  醇中 C-C 键的连续裂解和功能化已成为发现新转化的快速发展领域。然而，由于 C-C 键的固有惰性，以直接和选择性的方式实现它仍然具有挑战性。在此，我们报告了一种新颖且有效的方案，该方案能够通过多相氧化锰催化的醇中 C-C 键的连续裂解和酰胺化直接合成酰胺。范围广泛的伯醇和仲醇、1,2-二醇，甚至 β-O-4 和 β-1 木质素模型化合物都可以顺利地进行 C-C 键断裂，以提供单碳或多碳短酰胺。此外，反应条件的轻微改变允许醇的裂解和氰化以获得空间位阻腈。