1-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde | 40685-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde
• 英文别名: 1-methoxy-2-formyl-3,4-dihydronaphthalene；1-Methoxy-3,4-dihydronaphthalene-2-carbaldehyde
• CAS: 40685-42-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: VRIXVCGWNHYDRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde 在 四氯化钛 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (E)-1,2-bis(3,4-dihydro-1-methoxy-naphthalen-2-yl)ethylene
  参考文献：
  名称：

  (E)-1,2-Bis(3,4-dihydro-1-methoxynaphthalen-2-yl)ethylene

  摘要：

  In the structure of the title compound, C24H24O2, one of the two types of six-membered rings is planar and the other is in a skew-boat conformation. The ethylene C=C bond distance is 1.345 (3) Angstrom. The substituents at the ethylene are in an E configuration. The crystal structure consists of discrete molecules lying about inversion centres, held together by van der Waals contacts.

  DOI：

  10.1107/s010827019900921x
• 作为产物：
  描述：

  甲醇 、 1-氯-3,4-二氢-2-萘甲醛 在 sodium 作用下， 生成 1-methoxy-3,4-dihydronaphthalene-2-carboxaldehyde
  参考文献：
  名称：

  Synthesis, Characterization, Photophysical Properties of a Novel Organic Photoswitchable Dyad in Its Pristine and Hybrid Nanocomposite Forms

  摘要：

  在本文中，报道了新型有机二元体3-(1-甲氧基-3,4-二氢-萘-2-基-)-1-对氯苯基丙烯酮的合成和表征方法。在本文中，我们的主要目标是通过将有机二元体与不同的贵金属、半导体纳米粒子和贵金属-半导体核/壳纳米复合材料相结合来制造新型杂化纳米复合材料。在这个有机二元体中，供体部分是 1-甲氧基-3, 4-二氢-萘-2-甲醛，受体是对氯苯乙酮。我们对二元体及其混合纳米复合材料系统进行了稳态和时间分辨光谱测量。还使用Gaussian 03软件进行了一些量子化学计算，从理论角度支持了实验结果。理论预测和核磁共振研究表明，在基态下，仅存在二元体的延伸（E型或反式）构象，而在光激发下，这些延伸的构象异构体转化为折叠形式（Z型或顺式）的二元体，显示其光切换特性。时间分辨荧光光谱（TCSPC 方法的荧光寿命）测量表明，在氯仿介质中，本研究中研究的所有有机-无机杂化纳米复合材料，即使在激发单线态下，也相对于折叠构象体具有大量的延伸构象体。这表明相对于与二元组内的电荷分离相关的速率过程，能量破坏性电荷复合速率可能较慢。研究发现，在 CHCl3 介质中，对于单独的二元体和其他混合纳米复合材料系统，计算出的电荷分离率为 ∼108 s−1。从相应混合系统的瞬态吸收测量中观察到，该速率比浪费能量的电荷复合速率~102-101 s−1 更快。这表明构象几何形状对电荷分离和复合速率过程有很大影响。观察到的离子对寿命较长，暗示了本文研究的所有系统都适合构建高效的光能转换装置，特别是使用 Ag-Dyad 纳米复合材料。

  DOI：

  10.1166/jnn.2012.6208

文献信息

• Indium Mediated Allylation of β-Chloro-/β-Alkoxy Vinylaldehyde: A Facile One Pot Synthesis of 1-Chloro-/1-Alkoxy Hexa-1,5-diene-3-ol Derivatives
  作者：Dipanjan Pan、Gandhi K. Kar、Jayanta K. Ray

  DOI：10.1081/scc-120015553

  日期：2003.3

  Abstract Indium mediated allylation of β-chloro- or β-alkoxy vinylaldehydes in the presence of sodium iodide produce homoallylic alcohol derivatives (1-chloro-/1-alkoxy hexa-1,5-diene-3-ol derivatives) in good yields.

  摘要 在碘化钠存在下，铟介导的 β-氯-或 β-烷氧基乙烯醛的烯丙基化以良好的收率产生高烯丙醇衍生物（1-氯-/1-烷氧基六-1,5-二烯-3-醇衍生物）。
• Synthesis, Characterization, Photophysical Properties of a Novel Organic Photoswitchable Dyad in Its Pristine and Hybrid Nanocomposite Forms
  作者：Gopa Mandal、Amrita Chakraborty、Ujjal Kumar Sur、Balaprasad Ankamwar、Asish De、Tapan Ganguly

  DOI：10.1166/jnn.2012.6208

  日期：2012.6.1

  In the present paper the method of synthesis and characterization of a novel organic dyad, 3-(1-Methoxy-3,4-dihydro-naphthalyn-2-yl-)-1-p-chlorophenyl propenone, have been reported. In this paper our main thrust is to fabricate new hybrid nanocomposites by combining the organic dyad with different noble metals, semiconductor nanoparticle and noble metal-semiconductor core/shell nanocomposites. In this organic dyad, donor part is 1-Methoxy-3, 4-dihydro-naphthalen- 2-carboxaldehyde with the acceptor p-chloroacetophenone. We have carried out steady state and time-resolved spectroscopic measurements on the dyad and its hybrid nanocomposite systems. Some quantum chemical calculations have also been done using Gaussian 03 software to support the experimental findings by theoretical point of view. Both from the theoretical predictions and NMR studies it reveals that in the ground state only extended (E-type or trans-type) conformation of the dyad exists whereas on photoexcitation these elongated conformers are converted into folded forms (Z- or cis-type) of the dyad, showing its photoswitchable character. Time resolved fluorescence spectroscopic (fluorescence lifetime by TCSPC method) measurements demonstrate that in chloroform medium all the organic–inorganic hybrid nanocomposites, studied in the present investigation, possess larger amount of extended conformers relative to folded ones, even in the excited singlet state. This indicates the possibility of slower energy destructive charge recombination rates relative to the rate processes associate with charge-separation within the dyad. It was found that in CHCl3 medium, the computed charge separation rate was found to be ∼108 s−1 for the dyad alone and other hybrid nanocomposite systems. The rate is found to be faster than the energy wasting charge recombination rate ∼102–101 s−1, as observed from the transient absorption measurements for the corresponding hybrid systems. It indicates the conformational geometry has a great effect on the charge-separation and recombination rate processes. The suitability for the construction of efficient light energy conversion devices especially with Ag-Dyad nanocomposite of all the systems studied here is hinted from the observed long ion-pair lifetime.

  在本文中，报道了新型有机二元体3-(1-甲氧基-3,4-二氢-萘-2-基-)-1-对氯苯基丙烯酮的合成和表征方法。在本文中，我们的主要目标是通过将有机二元体与不同的贵金属、半导体纳米粒子和贵金属-半导体核/壳纳米复合材料相结合来制造新型杂化纳米复合材料。在这个有机二元体中，供体部分是 1-甲氧基-3, 4-二氢-萘-2-甲醛，受体是对氯苯乙酮。我们对二元体及其混合纳米复合材料系统进行了稳态和时间分辨光谱测量。还使用Gaussian 03软件进行了一些量子化学计算，从理论角度支持了实验结果。理论预测和核磁共振研究表明，在基态下，仅存在二元体的延伸（E型或反式）构象，而在光激发下，这些延伸的构象异构体转化为折叠形式（Z型或顺式）的二元体，显示其光切换特性。时间分辨荧光光谱（TCSPC 方法的荧光寿命）测量表明，在氯仿介质中，本研究中研究的所有有机-无机杂化纳米复合材料，即使在激发单线态下，也相对于折叠构象体具有大量的延伸构象体。这表明相对于与二元组内的电荷分离相关的速率过程，能量破坏性电荷复合速率可能较慢。研究发现，在 CHCl3 介质中，对于单独的二元体和其他混合纳米复合材料系统，计算出的电荷分离率为 ∼108 s−1。从相应混合系统的瞬态吸收测量中观察到，该速率比浪费能量的电荷复合速率~102-101 s−1 更快。这表明构象几何形状对电荷分离和复合速率过程有很大影响。观察到的离子对寿命较长，暗示了本文研究的所有系统都适合构建高效的光能转换装置，特别是使用 Ag-Dyad 纳米复合材料。
• Synthesis and biological evaluation of guanylhydrazone coactivator binding inhibitors for the estrogen receptor
  作者：Andrew L. LaFrate、Jillian R. Gunther、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1016/j.bmc.2008.10.007

  日期：2008.12

  Most patients with hormone-responsive breast cancer eventually develop resistance to traditional antiestrogens such as tamoxifen, and this has become a major obstacle in their treatment. We prepared and characterized the activity of a series of 16 guanylhydrazone small molecules that are designed to block estrogen receptor (ER) activity through a non-traditional mechanism, by directly interfering with coactivator binding to agonist-liganded ER. The inhibitory activity of these compounds was determined in cell-based transcription assays using ER-responsive reporter gene and mammalian two-hybrid assays. Several of the compounds gave IC50 values in the low micromolar range. Two secondary assays were used to confirm that these compounds were acting through the proposed non-traditional mode of estrogen inhibitory action and not as conventional antagonists at the ligand binding site. (c) 2008 Elsevier Ltd. All rights reserved.
• A frank synthesis of alkyl–aryl ethers from 2-halobenzaldehydes and aromatic olefins without transition metal co-catalyst and ligand
  作者：Balagani Sathish Kumar、Arvind S. Negi

  DOI：10.1016/j.tetlet.2015.03.086

  日期：2015.4

  An efficient synthesis of alkyl ethers has been developed for o-deactivated aryl halides and 1-halotetralenes. The method shows good regioselectivity towards ortho substituted halides. Alkali metal carbonates (Li2CO3/Na2CO3/K2CO3/Cs2CO3) have been used without a transition metal co-catalyst and ligand. The method is simple, straight-forward and proceeds to afford products in good isolated yields. The method holds potential for future applications in organic synthesis. (C) 2015 Elsevier Ltd. All rights reserved.
• (<i>E</i>)-1,2-Bis(3,4-dihydro-1-methoxynaphthalen-2-yl)ethylene
  作者：J. K. Ray、S. Gupta、S. Shanmuga Sundara Raj、H.-K. Fun

  DOI：10.1107/s010827019900921x

  日期：1999.11.15

  In the structure of the title compound, C24H24O2, one of the two types of six-membered rings is planar and the other is in a skew-boat conformation. The ethylene C=C bond distance is 1.345 (3) Angstrom. The substituents at the ethylene are in an E configuration. The crystal structure consists of discrete molecules lying about inversion centres, held together by van der Waals contacts.