1-methyl-1,2,3,4-tetrahydronaphthalene | 31291-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-methyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1-methyltetralin；1-Methyl-1,2,3,4-tetrahydro-naphthalin；5-methyltetralin
• CAS: 31291-71-1
• 化学式: C₁₁H₁₄
• mdl: MFCD09037621
• 分子量: 146.232
• InChiKey: APBBTKKLSNPFDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methyl-1,2,3,4-tetrahydronaphthalene 在 Pt/Al₂O₃ 作用下， 反应 1.0h， 生成 甲基萘
  参考文献：
  名称：

  用于结构分析的煤衍生烃中氢化芳烃组分的脱氢

  摘要：

  脱氢技术通过使用几种环烃进行评估，并成功地用于将煤衍生的非极性馏分中的加氢芳烃组分转化为相应的芳烃化合物。

  DOI：

  10.1246/bcsj.63.967
• 作为产物：
  描述：

  甲基萘 在 氢气 作用下， 240.0 ℃ 、5.0 MPa 条件下， 生成 1-methyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Hydroconversion of 1-methylnaphthalene over Pt/AlSBA-15–Al2O3 composite catalysts

  摘要：

  In the study, the novel Pt/AlSBA-15-Al2O3 composite catalysts varying in hydrogenation and acidic functions were analysed. The catalysts containing 1.5 and 2.5 wt.% of platinum were prepared by impregnation of the mixture of AlSBA-15 and boehmite (20 wt.%) powders with H2PtCl6 solution, which was followed by extrudation. Physicochemical properties of the catalysts were determined by N-2 sorption, XRD, XRF, Py-IR, H-2-O-2 titration, TEM and TOF-SIMS. Activity results performed under atmospheric pressure (240-350 degrees C, H-2:CH = 50 Nm(3)m(-3), W/F = 0.8 gs cm(-3)) revealed that the activity of 1.5%Pt/AlSBA-15-Al2O3 composite catalyst was much higher than that of 1.5%Pt/AlSBA-15 and 1.5%Pt/Al2O3 catalysts, due to the occurrence of a synergic effect between their components. It was found that an increase from 1.5 to 2.5 wt.% in platinum amount in the Pt/AlSBA-15-Al2O3 composite catalyst only slightly influences the 1-methylnaphthalene conversion (5.0 MPa, 240-380 degrees C, H-2: CH = 500 Nm(3) m(-3), WHSV = 2 h(-1)) but increases the selectivity to methyldecalins by 20% (at 350 degrees C). Yield of the desired ring opening products over 2.5%Pt/AlSBA-15-Al2O3 was low and did not exceed 6 wt.% at 380 degrees C. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2015.07.021

文献信息

• Reductive Activation and Hydrofunctionalization of Olefins by Multiphoton Tandem Photoredox Catalysis
  作者：Milena L. Czyz、Mitchell S. Taylor、Tyra H. Horngren、Anastasios Polyzos

  DOI：10.1021/acscatal.1c01000

  日期：2021.5.7

  of olefin feedstocks to architecturally complex alkanes represents an important strategy in the expedient generation of valuable molecules for the chemical and life sciences. Synthetic approaches are reliant on the electrophilic activation of unactivated olefins, necessitating functionalization with nucleophiles. However, the reductive functionalization of unactivated and less activated olefins with

  烯烃原料向结构复杂的烷烃的转化代表了重要的策略，可快速生成化学和生命科学领域有价值的分子。合成方法依赖于未活化烯烃的亲电子活化，因此必须用亲核试剂进行官能化。然而，用亲电子试剂将未活化的和活化程度较低的烯烃还原功能化仍然是合成化学中的一个持续挑战。在这里，我们报告通过光诱导直接单电子还原为相应的亲核自由基阴离子的惰性苯乙烯的亲核活化。该方法的核心是铱光催化剂[Ir（ppy）2（dtb-bpy）] PF 6的多光子串联光氧化还原循环，该循环触发原位形成高能光还原剂，该光还原剂可选择性地将苯乙烯烯烃π键还原为自由基阴离子，而无需化学计量的还原剂或溶解金属。这种温和的策略可以实现苯乙烯的化学选择性还原和加氢官能化，从而提供有价值的烷烃和叔醇衍生物。机理研究支持苯乙烯烯烃自由基阴离子中间体的形成和涉及两个连续单电子转移的Birch型还原。总体而言，这种烯烃活化的互补方式可实现低亲和度的烯烃与亲电试
• Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
  作者：Deliang Zhang、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1021/acs.orglett.9b01989

  日期：2019.8.2

  using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over

  描述了使用1，4-二恶烷作为氢供体的铱催化的烯烃的转移加氢。1,2-双（二环己基膦基）乙烷（DCyPE）的使用具有体积大和给电子高的特性，因此具有很高的催化活性。聚苯乙烯交联双膦PS-DPPBz产生了可重复使用的非均相催化剂。这些均质和非均质的方案实现了烯烃在其他可能还原的官能团（例如同一分子中的羰基，硝基，氰基和亚氨基）上的化学选择性转移加氢。
• Acceptorless Dehydrogenation of Hydrocarbons by Noble-Metal-Free Hybrid Catalyst System
  作者：Hiromu Fuse、Masahiro Kojima、Harunobu Mitsunuma、Motomu Kanai

  DOI：10.1021/acs.orglett.8b00583

  日期：2018.4.6

  acridinium photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst-enabled acceptorless dehydrogenation of hydrocarbons is reported. The cationic nickel complex played a critical role in the reactivity. This is the first example of acceptorless dehydrogenation of hydrocarbons by base metal catalysis under mild reaction conditions of visible light irradiation at room temperature.

  报道了一种混合催化，其包括a啶光氧化还原催化剂，硫代磷酸盐有机催化剂和镍催化剂使烃的无受体脱氢成为可能。阳离子镍络合物在反应性中起关键作用。这是在室温下可见光照射的温和反应条件下通过贱金属催化的烃的无受体脱氢的第一个例子。
• Domino Methylenation/Hydrogenation of Aldehydes and Ketones by Combining Matsubara's Reagent and Wilkinson's Catalyst
  作者：Radhouan Maazaoui、María Pin-Nó、Kevin Gervais、Raoudha Abderrahim、Franck Ferreira、Alejandro Perez-Luna、Fabrice Chemla、Olivier Jackowski

  DOI：10.1002/ejoc.201601137

  日期：2016.12

  reaction of aldehydes or ketones through a domino process involving two ensuing steps in a single pot is realized. The compatibility of Matsubara's reagent and Wilkinson's complex give a combination that allows, under dihydrogen, the transformation of a carbonyl function into a methyl group. This new method is suitable to introduce an ethyl motif from aromatic and aliphatic aldehydes with total chemoselectivity

  醛或酮的亚甲基化/加氢级联反应通过多米诺骨牌过程实现，该过程涉及两个随后的步骤在一个锅中。Matsubara 试剂和威尔金森复合物的相容性提供了一种组合，允许在二氢作用下将羰基官能团转化为甲基。这种新方法适用于从芳香族和脂肪族醛中引入乙基基序，具有总化学选择性和 α-立体化学纯度的总保留。开发的程序还扩展到从酮中引入甲基。
• Visible-Light-Induced Oxidation/[3 + 2] Cycloaddition/Oxidative Aromatization to Construct Benzo[<i>a</i>]carbazoles from 1,2,3,4-Tetrahydronaphthalene and Arylhydrazine Hydrochlorides
  作者：Jiaxuan Shen、Nannan Li、Yanjiang Yu、Chunhua Ma

  DOI：10.1021/acs.orglett.9b02939

  日期：2019.9.6

  An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism

  据报道，通过可见光串联氧化/ [3 + 2]环加成/氧化芳构化反应可有效合成苯并[a]咔唑。四氢萘的苄基C（sp3）-H通过可见光的光氧化还原催化剂在温和的反应条件下用氧气作为清洁氧化剂进行活化。该协议在广泛的底物范围内有效进行，并进行了机理研究。

表征谱图