2-phenyl-1-naphthaldehyde | 137869-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-1-naphthaldehyde
• 英文别名: 2-Phenylnaphthalene-1-carbaldehyde
• CAS: 137869-22-8
• 化学式: C₁₇H₁₂O
• 分子量: 232.282
• InChiKey: ZUJDQEYJDDBQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-phenyl-1-naphthaldehyde 以 乙腈 为溶剂， 反应 2.0h， 生成 屈
  参考文献：
  名称：

  Light-induced carbocyclization of iodoalkenes

  摘要：

  The direct irradiation of iodoalkenes leads to the formation of carbon-centered radical by homolysis of the C-I bond. The photoreaction is used in cyclizations with formation of six membered rings. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.056
• 作为产物：
  描述：

  2-甲氧基-1-萘甲酸 在 sodium tetrahydroborate 、 氯化亚砜 、 草酰氯 、 草酸 、 三乙胺 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 9.0h， 生成 2-phenyl-1-naphthaldehyde
  参考文献：
  名称：

  Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions

  摘要：

  An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.

  DOI：

  10.1021/ja00029a032

文献信息

• Copper catalyzed room temperature lactonization of aromatic C–H bond: a novel and efficient approach for the synthesis of dibenzopyranones
  作者：Raju Singha、Shubhendu Dhara、Munmun Ghosh、Jayanta K. Ray

  DOI：10.1039/c4ra13665a

  日期：——

  A novel and efficient methodology has been developed for the intramolecular aryl C–H oxidative lactonization of 2-arylbenzaldehyde using a low-cost CuCl catalyst and TBHP as the oxidant at room temperature.

  已开发出一种新颖高效的方法，用于在室温下使用低成本的CuCl催化剂和TBHP氧化剂对2-芳基苯甲醛进行分子内芳基C-H氧化内酯化。
• Regio- and Chemoselective Kumada–Tamao–Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions
  作者：Xuefeng Cong、Huarong Tang、Xiaoming Zeng

  DOI：10.1021/jacs.5b08621

  日期：2015.11.18

  the cross-coupling reactions with aryl ethers via C-O bond activation have attracted broad interest. However, the functionalizations of C-O bonds are mainly limited to nickel catalysis, and selectivity has long been a prominent challenge when several C-O bonds are present in the one molecule. We report here the first chromium-catalyzed selective cross-coupling reactions of aryl ethers with Grignard reagents

  作为一种环境友好的合成工具，通过 CO 键活化与芳基醚的交叉偶联反应引起了广泛的兴趣。然而，CO 键的功能化主要限于镍催化，当一个分子中存在多个 CO 键时，选择性一直是一个突出的挑战。我们在这里报告了第一个铬催化的芳基醚与格氏试剂通过 CO（烷基）键断裂的选择性交叉偶联反应。在室温下使用简单、廉价的铬 (II) 预催化剂结合亚氨基助剂实现了多种转化。它为高效和选择性地构建官能化芳香醛提供了新途径。
• Photochemistry of acyloximes: synthesis of heterocycles and natural products
  作者：Rafael Alonso、Alegría Caballero、Pedro J. Campos、Miguel A. Rodríguez

  DOI：10.1016/j.tet.2010.09.078

  日期：2010.11

  New applications of the photochemically generated iminyl radicals ring closure onto phenyl, thiophenyl, and pyridinyl rings are presented. The influence on the reactivity of different substituent throughout the acyloxime structure is discussed. Some observed effects are interpreted from computational studies. This reaction provides a new, simple, and straightforward method for the preparation of several

  提出了光化学产生的亚氨基自由基闭环在苯基，噻吩基和吡啶基环上的新应用。讨论了在整个肟肟结构中不同取代基对反应性的影响。通过计算研究可以解释一些观察到的影响。该反应为制备几种多环杂芳族化合物提供了一种新的，简单而直接的方法，它已被用于某些天然产物的合成中。
• Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates
  作者：Lei Fang、Weibin Lin、Chuanfeng Chen

  DOI：10.1016/j.cclet.2018.06.007

  日期：2018.8

  Abstract Tetrahydrobenzo[5]helicenediol (THB-[5]HDIOL) derivatives as additives for the efficient proline-catalyzed asymmetric List-Lerner-Barbas (LLB) aldol reactions of bulky aldehyde substrates was described. It was found that with dibromo-substituted helical diols P-4a/M-4a as additives, the proline-catalyzed LLB aldol reaction of 9-anthraldehyde and acetone gave the product in 83% yield and 99%

  摘要描述了四氢苯并[5]螺旋二醇（THB- [5] HDIOL）衍生物作为有效的脯氨酸催化大体积醛底物的不对称List-Lerner-Barbas（LLB）羟醛反应的添加剂。发现用二溴取代的螺旋二醇P-4a / M-4a作为添加剂，脯氨酸催化的9-乙醛和丙酮的LLB羟醛缩醛反应以83％的收率和99％的ee得到产物。过渡态模型显示TS（R）中的蒽基和添加剂的苯基之间存在边对面的π-π堆积，这可能导致高对映选择性。
• Organocatalytic Enantioselective Construction of Conformationally Stable C(sp²)–C(sp³) Atropisomers
  作者：Giulio Bertuzzi、Vasco Corti、Joseph A. Izzo、Sebastijan Ričko、Nicolaj Inunnguaq Jessen、Karl Anker Jørgensen

  DOI：10.1021/jacs.1c12619

  日期：2022.1.19

  observed in natural compounds; however, their enantioselective synthesis remains almost completely unexplored. Herein we disclose a new class of chiral C(sp2)–C(sp3) atropisomers obtained with high levels of stereoselectivity (up to 99% ee) by means of an organocatalytic asymmetric methodology. Multiple molecular motifs could be embedded in this class of C(sp2)–C(sp3) atropisomers, showing a broad and general

  非联芳基阻转异构体是由具有至少一个壬芳烃部分的立体轴定义的分子。其中，在天然化合物中观察到具有构象稳定的 C(sp 2 )-C(sp 3 ) 立体轴的支架。然而，它们的对映选择性合成仍然几乎完全未被探索。在此，我们公开了通过有机催化不对称方法获得的具有高立体选择性（高达 99% ee）的新型手性 C(sp 2 )–C(sp 3 ) 阻转异构体。此类 C(sp 2 )–C(sp 3 ) 中可嵌入多个分子基序) 阻转异构体，显示了广泛而通用的协议。实验数据有力地证明了所得化合物中 C(sp 2 )–C(sp 3 ) 立体轴的构象稳定性（高达t 1/2 25  ° C >1000 y），并显示了对这种罕见立体异构体的动力学控制元素。这与密度泛函理论计算相结合，表明观察到的立体选择性源于建立中间体平衡的 Curtin-Hammett 情景。此外，实验研究为中心到轴向手性转换的工作原理提供了证据。