3,4-dihydronaphthalene-1-carbaldehyde | 93340-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydronaphthalene-1-carbaldehyde
• CAS: 93340-32-0
• 化学式: C₁₁H₁₀O
• mdl: MFCD18810645
• 分子量: 158.2
• InChiKey: MODDDHSZWBNKAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  3,4-dihydronaphthalene-1-carbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 戊烯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 生成 1,2,3,4,-四氢-1-萘甲酸甲酯
  参考文献：
  名称：

  八千五百万岁久久琥珀中久久藤醇的两种对映异构体的合成及生物活性

  摘要：

  通过全合成确定降冰片烷萜类化合物，苦瓜糖醇（1）的完整结构。总合成的关键特征是（1）通过苯甲酰胺的邻位化来安装异戊基；（2）通过RCM反应构建四氢萘酮；（3）使用色谱分离法测定（±）-1的光学拆分度。相应的樟脑。从极性更大的樟脑酸酯获得的对-溴苯甲酸酯的X射线晶体学分析与天然衍生物相同，表明天然的苦瓜酚具有S-构型。天然对映体及其（R）-对映体对突变酵母和HL - 60细胞具有相同的抑制活性，而在C-8和（±）-1的9位上没有烷基的简单类似物则没有这种活性。

  DOI：

  10.1016/j.bmcl.2012.05.022
• 作为产物：
  描述：

  3,4-二氢萘-1-腈 在 二异丁基氢化铝 作用下， 以40%的产率得到3,4-dihydronaphthalene-1-carbaldehyde
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019

文献信息

• Pd-Catalyzed Carbonylation of Vinyl Triflates To Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions
  作者：Shaoke Zhang、Helfried Neumann、Matthias Beller

  DOI：10.1021/acs.orglett.9b00765

  日期：2019.5.17

  An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access

  开发了一种有效的通用方案，可通过乙烯基三氟甲磺酸酯的羰基化反应合成α，β-不饱和醛，酯和酰胺，包括樟脑，酮异佛尔酮，马鞭草酮和普乐酮。这些转化的关键是使用含有吡啶基取代的d t bpx型配体的特定钯催化剂。该方法还使得容易从相应的酮获得二羰基化产物。
• Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System
  作者：Quan Zhu、Yunsong Luo、Yongyan Guo、Yushun Zhang、Yunhai Tao

  DOI：10.1021/acs.joc.0c02987

  日期：2021.4.16

  system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical

  Saegusa氧化的高效实用的Pd（II）/ Cu（OAc）2-催化剂体系，可在无配体的情况下以极低的催化剂负载量（500 mol ppm）将烯醇醚转化为具有多种底物的相应烯醛和水性条件，描述。催化剂体系在重要的自然分子上的大规模应用证明了其合成用途。这项工作使Saegusa氧化成为制备enals的一种高度实用的方法，并且还为对Pd（II）/ Cu（II）-用于羰基化合物脱氢和降低Pd-催化剂负载量的催化剂体系提出了新的见解。
• Lewis Acid-Catalyzed Tandem Diels−Alder Reaction/Retro-Claisen Rearrangement as an Equivalent of the Inverse Electron Demand Hetero Diels−Alder Reaction
  作者：Huw M. L. Davies、Xing Dai

  DOI：10.1021/jo050821s

  日期：2005.8.1

  A highly stereoselective formal inverse electron demand hetero Diels−Alder reaction (HDA) occurs on reaction of 2-aryl-α,β-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels−Alder reaction/retro-Claisen rearrangement.

  在2-芳基-α，β-不饱和醛与环戊二烯的反应中会发生高度立体选择性的形式逆电子需求杂狄尔斯-阿尔德反应（HDA）。该转化的主要途径显示为路易斯酸催化的串联狄尔斯-阿尔德反应/复古克莱森重排。
• Brønsted Acid Catalyzed Intramolecular Hydroarylation for the Synthesis of Cycloalkenyl Selenides and Tellurides
  作者：Dahan Eom、Sangjune Park、Youngchul Park、Kooyeon Lee、Gilbert Hong、Phil Ho Lee

  DOI：10.1002/ejoc.201201763

  日期：2013.5

  Trifluoromethanesulfonic acid catalyzed intramolecular hydroarylation of alkynyl selenides and tellurides is developed for the preparation of cycloalkenyl selenide and telluride derivatives through a selective 6- and 7-endo mode. The cycloalkenyl selenides and tellurides can be easily converted into a wide range of other valuable functionalities, including cyclic olefins, allylic alcohols, enynes,

  三氟甲磺酸催化的炔基硒化物和碲化物的分子内加氢芳基化被开发用于通过选择性 6- 和 7-endo 模式制备环烯基硒化物和碲化物衍生物。环烯基硒化物和碲化物可以很容易地转化为各种其他有价值的官能团，包括环烯烃、烯丙醇、烯炔、1,3-二烯和 α,β-不饱和醛。
• Origin of the preference for the chair conformation in the Cope rearrangement. Effect of phenyl substituents on the chair and boat transition states
  作者：K. J. Shea、G. J. Stoddard、W. P. England、C. D. Haffner

  DOI：10.1021/ja00033a042

  日期：1992.3

  4-tetrahydronaphthalenes] 8 and 9 were synthesized, and the activation energy parameters for their unimolecular [3,3] sigmatropic rearrangement to 1,2-bis(3,4-dihydro-1-naphthalenyl)ethane (13) were determined. The d,l(diastereomer is constrained to undergo Cope rearrangement in the chair conformation while the meso diastereomer is constrained to the boat. At 150 o C k d,l /k meso =7×10 6

  合成了 d,l- 和 meso-2,2'-双 [1-methylene-1,2,3,4-tetrahydronaphthalenes] 8 和 9，以及它们单分子 [3,3] σ 重排的活化能参数为测定了 1,2-双(3,4-二氢-1-萘基)乙烷 (13)。d,l(非对映异构体被限制在椅子构象中进行 Cope 重排，而内消旋非对映异构体被限制在船形上。在 150 o C kd,l /k meso =7×10 6