naphthalen-2-yl(pyridin-3-yl)methanone | 89242-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl(pyridin-3-yl)methanone
• 英文别名: 2-naphthyl 3-pyridyl ketone；[2]naphthyl-[3]pyridyl ketone；[2]Naphthyl-[3]pyridyl-keton
• CAS: 89242-98-8
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: LPSAFZGCRBBION-UHFFFAOYSA-N

物化性质

• 熔点：
  71-72 °C
• 沸点：
  419.9±18.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl(pyridin-3-yl)methanone 生成 (Z)-7-Naphthalen-2-yl-7-pyridin-3-yl-hept-6-enoic acid
  参考文献：
  名称：

  SHINJI, TERAO;KOBEI, NISHIKAWA

  摘要：

  DOI：
• 作为产物：
  描述：

  Naphthalen-2-yl(pyridin-3-yl)methanol 生成 naphthalen-2-yl(pyridin-3-yl)methanone
  参考文献：
  名称：

  TEHRAO, SINDZI;NISIKAVA, KOXEHJ

  摘要：

  DOI：

文献信息

• HMPA-Catalyzed Transfer Hydrogenation of 3-Carbonyl Pyridines and Other N-Heteroarenes with Trichlorosilane
  作者：Yun Fu、Jian Sun

  DOI：10.3390/molecules24030401

  日期：——

  A method for the HMPA (hexamethylphosphoric triamide)-catalyzed metal-free transfer hydrogenation of pyridines has been developed. The functional group tolerance of the existing reaction conditions provides easy access to various piperidines with ester or ketone groups at the C-3 site. The suitability of this method for the reduction of other N-heteroarenes has also been demonstrated. Thirty-three examples of different substrates have been reduced to designed products with 45–96% yields.

  已经开发出一种六甲基磷酰三胺（HMPA）催化的无金属转移氢化吡啶的方法。现有反应条件下的官能团耐受性使得容易获得C-3位点带有酯基或酮基的各种哌啶。还证明了这种方法适用于还原其他N-杂芳烃。已经有33个不同底物的例子被还原为设计的产品，产率为45-96%。

• Hydrogenative Dearomatization of Pyridine and an Asymmetric Aza‐Friedel–Crafts Alkylation Sequence
  作者：Shuo‐Guo Wang、Shu‐Li You

  DOI：10.1002/anie.201309876

  日期：2014.2.17

  Highly efficient synthesis of enantiomerically enriched substituted piperidines has been realized via chiral phosphoric acid catalyzed cascade hydrogenative dearomatization of substituted pyridines and aza‐Friedel‐Crafts reaction in good to excellent yields and enantioselectivity.

  对映体富集的取代哌啶的高效合成已通过手性磷酸催化取代的吡啶的级联氢化脱芳香化反应和氮杂-Friedel-Crafts反应获得了良好的收率和对映选择性。
• Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence
  作者：Zi-Lei Xia、Chao Zheng、Shou-Guo Wang、Shu-Li You

  DOI：10.1002/anie.201712435

  日期：2018.3.1

  A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity

  已经开发了通过手性磷酸催化的烯胺异构化/螺环化/转移氢化序列通过吲哚基二氢吡啶的催化不对称脱芳香化反应来高效合成富含对映体的螺二氢吲哚。该反应在温和的反应条件下进行，以良好的对映选择性（高达97％ee）提供了产率高（高达88％）的新型螺二氢吲哚。DFT计算提供了对反应机理以及立体化学起源的深刻见解。
• Formal Umpolung Addition of Phosphites to 2‐Azaaryl Ketones under Chiral Brønsted Base Catalysis: Enantioselective Protonation Utilizing [1,2]‐Phospha‐Brook Rearrangement
  作者：Azusa Kondoh、Takayuki Hirozane、Masahiro Terada

  DOI：10.1002/chem.202201240

  日期：2022.7.26

  The catalytic enantioselective protonation of α-oxygenated (2-azaaryl)methyl anions generated through the formal umpolung addition of the anion of dialkyl phosphites to 2-azaaryl ketones utilizing the [1,2]-phospha-Brook rearrangement was demonstrated with chiral bis(guanidino)iminophosphorane organosuperbase. This is a rare example of the catalytic enantioselective protonation of transient carbanions

  使用 [1,2]-phospha-Brook 重排，通过将亚磷酸二烷基酯的阴离子正式 umpolung 加成到 2-氮杂芳基酮中产生的 α-氧化 (2-氮杂芳基)甲基阴离子的催化对映选择性质子化反应用手性双(胍基）亚氨基正膦有机超碱。这是一个罕见的例子，催化对映选择性质子化除了烯醇化物以外的瞬时碳负离子，构建了一个三取代的立体中心 α 到 2-氮杂芳烃。
• Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of .omega.-pyridylalkenoic acids
  作者：Kaneyoshi Kato、Shigenori Ohkawa、Shinji Terao、Zenichi Terashita、Kohei Nishikawa

  DOI：10.1021/jm00381a005

  日期：1985.3

  A novel series of omega-pyridylalkenoic acids has been prepared by applying the Wittig reaction. Modifications were made in the omega-aryl moiety, the alkylene chain length, the alpha-methylene group adjacent to the carbonyl group, and the carboxyl group of the molecule. The compounds were tested as inhibitors of thromboxane synthetase in an in vitro assay and in ex vivo experiments with the rat. Most members of this new class of thromboxane synthetase inhibitors (TXSI) showed good activity in both assay systems. (E)-7-Phenyl-7-(3-pyridyl)-6-heptenoic acid (9c; CV-4151) was one of the most potent compounds in in vitro enzyme inhibition (IC50 = 2.6 X 10(-8) M) and, when orally administered, the most potent and long acting in the inhibition of blood thromboxane A2 production in the rat. New conceptual models I-III for the enzyme-substrate (prostaglandin H2, PGH2) and the enzyme-TXSI interactions are proposed for understanding the molecular design and structure-activity relations.