5-(萘-2-基)戊-2-酮 | 103094-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-(萘-2-基)戊-2-酮
• 英文名称: 5-(naphthalen-2-yl)pentan-2-one
• 英文别名: 5-(2-Naphthyl)pentan-2-one；5-naphthalen-2-ylpentan-2-one
• CAS: 103094-37-7
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: HTSGUHNOFLKJDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43.5 °C(Solv: hexane (110-54-3))
• 沸点：
  365.3±21.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  5-(萘-2-基)戊-2-酮 以26%的产率得到
  参考文献：
  名称：

  SHONO TATSUYA; KISE NAOKI; SUZUMOTO TAKESHI; MORIMOTO TOSHIO, J. AMER. CHEM. SOC., 108,(1986) N 15, 4676-4677

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-2-萘丁醛 在 偶氮二异丁腈 、 三正丁基氢锡 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 5-(萘-2-基)戊-2-酮
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053

文献信息

• A New, Efficient and Stereoselective Synthesis of Tricyclic and Tetracyclic Compounds by Samarium Diiodide Induced Cyclisations of Naphthyl-Substituted Arylketones—An Easy Access to Steroid-Like Skeletons
  作者：Francesca Aulenta、Mathias Berndt、Irene Brüdgam、Hans Hartl、Sebastian Sörgel、Hans-Ulrich Reißig

  DOI：10.1002/chem.200700057

  日期：2007.7.16

  we present the application of samarium diiodide induced cyclisations of naphthyl-substituted ketones towards an easy and stereoselective access to tri- and tetracyclic-functionalised compounds. Typical naphthalene derivatives were studied to investigate the scope and limitations of this novel cyclisation process. The model substrates studied demonstrate that the samarium ketyl cyclisations are essentially

  在本报告中，我们介绍了由二碘化sa诱导的萘基取代的酮的环化，其对三环和四环官能化化合物的容易和立体选择。对典型的萘衍生物进行了研究，以研究这种新型环化方法的范围和局限性。所研究的模型底物表明，酮基环化基本上仅限于六元环的形成。这些反应的非对映选择性受到烷基侧链与萘核的连接的强烈影响。γ-萘-1-基取代的酮提供环化产物，例如17或22-26，为单一非对映异构体，相反，γ-萘-2-基取代的前体可得到非对映异构体的混合物-如模型化合物10转化为三环产物18a / 18b或环己酮衍生物33转化为四环非对映异构体34a / 34b所证明。作为酮基前体的环状酮提供了类固醇状的四环骨架。然而，由于环B / C和C / D的顺式/顺式融合，这些产物具有“不自然的”碗状形状。X射线分析已鉴定出几种环化产物，不仅证明了结构，而且证明了相对构型和优选构象。类固醇类似物23经历随后的转化，这表明此类化合物的类苯乙
• Electroorganic chemistry. 98. Novel intramolecular stereoselective addition of electrogenerated radical species to the aromatic ring
  作者：Tatsuya. Shono、Naoki. Kise、Takeshi. Suzumoto、Toshio. Morimoto

  DOI：10.1021/ja00275a084

  日期：1986.7

  La reduction electrochimique de derives de l'aryl-5 pentanone-2 conduit a des derives de l'(hexahydro-1,2,3,4,6,8a methyl-1) naphtol-1

  La 还原电化学 de 衍生 de l'aryl-5 pentanone-2 导管 a des 衍生 de l'(hexahydro-1,2,3,4,6,8amethyl-1)naphtol-1
• METHOD FOR CONTROLLING ARTHROPOD PEST
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150344466A1

  公开（公告）日：2015-12-03

  An amide compound represented by formula (I): [wherein A represents a 3- to 7-membered saturated heterocyclic ring which contains, as ring-forming component(s), one or more atoms or groups selected from the group consisting of an oxygen atom and —S(O) t —, t represents 0, etc., R 1 and R 2 are the same or different and represent a hydrogen atom, etc., n represents 0, etc., the following formula (II): represents a 5-membered aromatic ring, in which Z represents a nitrogen atom or a carbon atom and X 1 , X 2 and X 3 are the same or different and represent a nitrogen atom, etc., R 3 and R 4 are the same or different and represent a hydrogen atom, etc., m represents 0 to 2, Q represents one group selected from group A or a C1 to C8 chain hydrocarbon group optionally having one group selected from group A, Y represents an oxygen atom, etc., u represents 0, etc., and v represents 0, etc.] has excellent arthropod pest controlling effects.

  化合物式(I)所代表的酰胺化合物：[其中A代表一个3到7个成员的饱和杂环环，该环包含作为环构成组分之一或多个原子或基团，所选自氧原子和—S（O）t—群，t代表0等；R1和R2相同或不同，代表氢原子等；n代表0等；下列式子(II)代表一个5个成员的芳香环，在该环中Z代表一个氮原子或一个碳原子，X1、X2和X3相同或不同，代表氮原子等，R3和R4相同或不同，代表氢原子等，m代表0到2，Q代表从群A中选择的一个群或一个C1到C8链烃基团，该基团可以选择从群A中选择的一个群，Y代表氧原子等，u代表0等，v代表0等]具有优良的节肢动物害虫控制效果。
• Formal γ-C(sp³)–H Activation of Ketones via Microwave-Promoted and Iminyl-Radical-Mediated 1,5-Hydrogen Atom Transfer
  作者：Jatinder Singh、Spencer A. Jones、Tanner J. Nelson、Jesus A. Botello、Steven L. Castle

  DOI：10.1021/acs.joc.3c00915

  日期：2023.7.21

  O-phenyloximes triggers N–O homolysis and 1,5-hydrogen atom transfer (HAT), resulting in formal γ-C–H functionalization of ketones after trapping of the radical intermediate and in situ imine hydrolysis. The Lewis acid InCl3·H2O facilitated HAT, enabling functionalization of benzylic and nonbenzylic secondary carbon atoms. Functionalization of primary carbons was feasible but afforded low yields, requiring

  O-苯基肟的微波辐射引发 N-O 均裂和 1,5-氢原子转移 (HAT)，在捕获自由基中间体和原位亚胺水解后，导致酮的正式 γ-C-H 官能化。路易斯酸InCl 3 ·H 2 O促进HAT，使苄基和非苄基仲碳原子官能化。伯碳的官能化是可行的，但收率低，需要ClCH 2 CO 2 H代替InCl 3 ·H 2 O作为添加剂。C-O和C-C键的形成都可以通过这种方法完成。
• Optically active naphthalene derivative, process for preparation thereof, liquid crystal composition containing the same as effective component, and liquid crystal element using the same
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0416946A2

  公开（公告）日：1991-03-13

  Disclosed herein are a novel optically active naphthalene derivative, a process of the preparation thereof a ferroelectric liquid crystal composition containing the same and a liquid crystal element using the composition. The above optically active naphthalene derivatives including optically active naphthylcarboxylic acid derivative, hydroxynaphthalene derivative, alkoxynaphthylalkanol derivative and alkylnaphthylalkanol derivative have the following structural formula: wherein R' denotes an alkyl group of 3-20 carbon atoms, R2 denotes an alkyl group of 1-20 carbon atoms optionally substituted with halogen atom(s) or an alkoxyalkyl group of 2-20 carbon atoms optionally substituted with halogen atom(s), X denotes -COO- or -OCO-, k, t and m denotes 0 or 1 respectively, n denotes an integer of 0-6, p denotes 0 or 1, and an asterisk indicates an asymmetric carbon atom, proviso when k is 0, t and m are not 1 at the same time, when k is 1, m is 1, and when n is 0 and m is 1, X is -COO-. These optically active naphthalene derivatives are useful as a ferroelectric liquid crystal material or its component having a sufficient spontaneous polarization and by which a high speed response is possible and which further exhibits a ferroelectric liquid crystal phase in a temperature region around room temperature.

  本文公开了一种新型光学活性萘衍生物、其制备工艺、含有该衍生物的铁电液晶组合物以及使用该组合物的液晶元件。 上述光学活性萘衍生物包括光学活性萘甲酸衍生物、羟基萘衍生物、烷氧基萘烷醇衍生物和烷基萘烷醇衍生物，其结构式如下： 其中 R' 表示 3-20 个碳原子的烷基，R2 表示 1-20 个碳原子的烷基，可选择被卤素原子取代，或 2-20 个碳原子的烷氧基烷基，可选择被卤素原子取代，X 表示 -COO- 或 -OCO-、k、t 和 m 分别表示 0 或 1，n 表示 0-6 的整数，p 表示 0 或 1，星号表示不对称碳原子，但当 k 为 0 时，t 和 m 不能同时为 1，当 k 为 1 时，m 为 1，当 n 为 0 而 m 为 1 时，X 为-COO-。 这些具有光学活性的萘衍生物可用作铁电液晶材料或其成分，它们具有足够的自发极化，可实现高速响应，并在室温附近的温度区域进一步显示出铁电液晶相。