2-benzyl-1-tetralone | 27019-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-benzyl-1-tetralone
• 英文别名: 2-benzyl-3,4-dihydronaphthalen-1(2H)-one；2-benzyl-3,4-dihydronaphthalen-1-one；1(2H)-Naphthalenone, 3,4-dihydro-2-(phenylmethyl)-；2-benzyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 27019-08-5
• 化学式: C₁₇H₁₆O
• mdl: MFCD16516891
• 分子量: 236.313
• InChiKey: LWBKNBIUKKTGEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  176 °C(Press: 1 Torr)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-tetralone 在 sodium tetrahydroborate 作用下， 生成 2-benzyl-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  七种高异黄酮、六种硫代高异黄酮和四种结构相关化合物的结构研究

  摘要：

  摘要 基于 PFG 1H、13C HMQC 和 HMBC 实验对 3-(4'-X-苄基)-4-色酮 (Ia, X = CN 和 Ib, X = NO2) 确定并分配了 1H 和 13C NMR 化学位移, 3-(4'-X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4'-X-benzylidene)-4-chromanones (IIIa– IIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4'-X-亚苄基)4-硫代色满酮 (IVa–IVd, X = Cl, Br, F, OCH3 )、2-苄基-1,2,3,4-四氢-1-萘酚 (V)、2-苄基-和 (E)-2-亚苄基-1-四氢萘酮 (VI 和 VII)，和 (E)- 2-benzylidene-1-benzosuberol

  DOI：

  10.1007/s11224-011-9860-6
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H₂O) 、 caesium carbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 生成 2-benzyl-1-tetralone
  参考文献：
  名称：

  Synthesis of a-Alkylated Ketones via Tandem Acceptorless Dehydrogenation/a-Alkylation from Secondary and Primary Alcohols Catalyzed by Metal–Ligand Bifunctional Iridium Complex [Cp*Ir(2,2′-bpyO)(H₂O)]

  摘要：

  A new strategy for the synthesis of alpha-alkylated ketones via tandem acceptorless dehydrogenation/alpha-alkylation from secondary and primary alcohols was proposed and accomplished. In the presence of metal-ligand bifunctional iridium complex [Cp*Ir(2,2'-bpyO)(H2O)], various desirable products were obtained in high yields. Compared with previous methods for the direct dehydrogenative coupling of secondary alcohols with primary alcohols to alpha-alkylated ketones, this protocol has obvious advantages including complete selectivity for alpha-alkylated ketones and more environmentally benign conditions. Notably, the study also exhibited the potential to develop tandem reactions catalyzed using a metal-ligand bifunctional iridium complex.

  DOI：

  10.1021/acs.joc.5b01975

文献信息

• Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources
  作者：Binbin Huang、Yanan Li、Chao Yang、Wujiong Xia

  DOI：10.1039/c9cc02368b

  日期：——

  sustainable, chemoselective 1,4-reduction of α,β-unsaturated ketones by means of an electrochemical method is presented, wherein the extremely inexpensive ammonium chloride (NH4Cl) is applied as the only additive. The reaction proceeds smoothly in the air at ambient temperature. Mechanistic studies reveal that both NH4Cl and solvent methanol work as hydrogen donors.

  提出了通过电化学方法可持续的，化学选择性的α，β-不饱和酮的1，4-还原，其中极其廉价的氯化铵（NH 4 Cl）被用作唯一的添加剂。反应在环境温度下在空气中平稳进行。机理研究表明，NH 4 Cl和溶剂甲醇均可作为氢供体。
• Nickel‐Catalyzed Selective Synthesis of α‐Alkylated Ketones via Dehydrogenative Cross‐Coupling of Primary and Secondary Alcohols
  作者：Amreen K Bains、Ayanangshu Biswas、Debashis Adhikari

  DOI：10.1002/adsc.202101077

  日期：2022.1.4

  air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result α-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated α,β-unsaturated ketone. Preliminary

  在此，我们描述了一种可分离的、空气稳定的、均相的镍催化剂，该催化剂在仲醇和伯醇之间进行脱氢交叉偶联反应，以选择性地产生 α-烷基化酮产物。该一锅反应中涉及的步骤顺序是两种醇的脱氢、酮和醛之间的缩合以及原位生成的 α,β-不饱和酮的氢化。初步的机理研究暗示了借氢反应后的激进机制。
• Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis
  作者：Milan K. Barman、Akash Jana、Biplab Maji

  DOI：10.1002/adsc.201800380

  日期：2018.9.3

  a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol. The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions

  在此，我们报告了一种非常简单且便宜的催化体系，该体系基于地球上大量的过渡金属锰和稳定的无膦NNN钳位配体，可通过氢自动转移C-与伯醇进行酮的原子高效α-烷基化C键形成协议。该预催化剂可以原位产生，并且可以通过在较温和的条件下使用催化量的碱来活化。酮类与多种伯醇可有效地多样化，分离收率良好至极佳。值得注意的是，该催化剂也可用于以2-氨基苄醇为烷基化剂的喹啉衍生物的合成。后面的反应是高度良性的，仅产生氢和水作为副产物。
• Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones
  作者：Qing Xu、Jianhui Chen、Haiwen Tian、Xueqin Yuan、Shuangyan Li、Chongkuan Zhou、Jianping Liu

  DOI：10.1002/anie.201308642

  日期：2014.1.3

  Direct dehydrative α‐alkylation reactions of ketones with alcohols are now realized under simple, practical, and green conditions without using external catalysts. These catalyst‐free autocatalyzed alkylation methods can efficiently afford useful alkylated ketone or alcohol products in a one‐pot manner and on a large scale by CC bond formation of the in situ generated intermediates with subsequent

  现在，在简单，实用和绿色的条件下，无需使用外部催化剂即可实现酮与醇的直接α-烷基脱水反应。这些无催化剂的自动催化烷基化方法可以通过原位生成的中间体的CC键形成以及随后可控和选择性的Meerwein–Pondorf–Verley– Oppenauer型氧化还原工艺。
• Ruthenium-Catalyzed Conjugate Hydrogenation of α,β-Enones by in situ Generated Dihydrogen from Paraformaldehyde and Water
  作者：Wanfang Li、Xiao-Feng Wu

  DOI：10.1002/ejoc.201403359

  日期：2015.1

  Notwithstanding that the highly selective hydrogenation of α,β-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in α,β-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various α,β-enones to saturated ketones with high selectivity was investigated

  尽管使用 Noyori 的 Ru 双功能系统可以实现 α,β-烯酮向烯丙醇的高度选择性氢化，但在不接触 C=O 键的情况下选择性还原 α,β-烯酮中的 C=C 键仍然缺乏通用、简单、高效的程序。研究了钌催化的各种α,β-烯酮以高选择性共轭氢化成饱和酮。该程序最重要的特点是由多聚甲醛（或福尔马林）和水原位产生的氢气用作还原剂。