5-(naphthalen-1-yl)pentan-2-one | 602330-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-1-yl)pentan-2-one
• 英文别名: 5-Naphthalen-1-ylpentan-2-one
• CAS: 602330-49-4
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: OKKLDBQTNPJUPY-UHFFFAOYSA-N

物化性质

• 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-(naphthalen-1-yl)pentan-2-one 在 samarium diiodide 、 水 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以99%的产率得到5-(naphthalen-1-yl)pentan-2-ol
  参考文献：
  名称：

  溴化锂/水作为Sa-乙炔基（杂）芳烃环芳烃脱芳香化反应的添加剂

  摘要：

  据报道使sa-酮基（杂）芳烃环化脱芳香化的新条件。在这些由二碘化sa介导的反应的许多示例中，溴化锂和水可以代替致癌和诱变的六甲基磷酰胺（HMPA）用作添加剂。N-酰化吲哚衍生物的环化反应获得了最佳结果，从而以预期的产率和良好的非对映选择性提供了预期的二氢吲哚。还描述了一种新型的环化反应，可提供吲哚基取代的烯丙基衍生物。讨论了溴化锂/水系统的范围和局限性。

  DOI：

  10.1002/chem.201502912
• 作为产物：
  描述：

  (E)-5-Naphthalen-1-yl-pent-3-en-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-(naphthalen-1-yl)pentan-2-one
  参考文献：
  名称：

  Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3-d]pyrimidines

  摘要：

  A series of 6-aralkyl substituted 2,4-diaminothieno[2,3-d]pyrimidines in which the 6-aryl group is separated from the thieno[2,3-d]pyrimidine ring by two to five methylene groups were synthesized and studied as inhibitors of dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liver. Compounds in which the thieno[2,3-d]pyrimidine ring is separated from the 6-aryl substituent by three methylene groups were the most potent inhibitors of the series (with IC50 values ranging from 0.24 and 11.0 muM) but those with two methylene groups between the aromatic rings were the most selective agents. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00101-6

文献信息

• Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones
  作者：Bao-Yin Zhao、Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.0c04174

  日期：2021.2.19

  An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。
• Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives
  作者：Mansour Dolè Kerim、Shuanglong Jia、Chrysoula Theodorakidou、Sébastien Prévost、Laurent El Kaïm

  DOI：10.1039/c8cc06536e

  日期：——

  the formation of a palladium π-allyl complex followed by a base-promoted β-hydride elimination. This reaction, combined with the condensation of ketones with nitromethane and the functionalization of the resulting nitrocycloalkenes, constitutes a very powerful synthetic tool for the formation of dienes. Particular attention has been brought to the application of this methodology to the formation of

  在钯催化剂的存在下，在碱性处理下，通过消除硝基，将硝基烯丙基衍生物转化为二烯。该反应可能涉及形成钯π-烯丙基络合物，然后消除碱促进的β-氢化物。该反应与酮与硝基甲烷的缩合以及所得硝基环烯烃的官能化相结合，构成了用于形成二烯的非常强大的合成工具。特别注意了该方法在从1-四氢萘酮形成1-取代萘中的应用。
• 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
• Replacement of HMPA in Samarium Diiodide Promoted Cyclizations and Reactions of Organolithium Compounds
  作者：Mathias Berndt、Alexandra Hölemann、André Niermann、Christoph Bentz、Reinhold Zimmer、Hans-Ulrich Reissig

  DOI：10.1002/ejoc.201101830

  日期：2012.3

  Tripyrrolidinophosphoric acid triamide (TPPA) can replace carcinogenic HMPA as a Lewis basic additive in many reactions involving samarium ketyls. In most cases, yields and selectivities of cyclizations of (het)aryl, alkenyl, and alkynyl ketones are similar. TPPA is also a good substitute of HMPA in the O-silylation of an ester enolate and in reactions oflithiated 1,3-dithiane. All these results clearly

  Tripyrrolidinophosphoric acid triamide (TPPA) 可以在许多涉及钐羰基化合物的反应中替代致癌的 HMPA 作为路易斯碱性添加剂。在大多数情况下，（杂）芳基、烯基和炔基酮环化的产率和选择性是相似的。在酯烯醇化物的 O-甲硅烷基化和锂化 1,3-二噻烷的反应中，TPPA 也是 HMPA 的良好替代品。所有这些结果清楚地表明，在许多情况下可以避免使用 HMPA。
• Samarium(II)‐Promoted Cyclizations of Nonactivated Indolyl Sulfinyl Imines to Polycyclic Tertiary Carbinamines
  作者：Chintada Nageswara Rao、Hans‐Ulrich Reissig

  DOI：10.1002/ejoc.202200264

  日期：2022.4.12

  of samarium diiodide in the presence of water and lithium bromide efficiently converts nonactivated N-acylated indolyl sulfinyl imines into polycyclic indoline derivatives containing a tertiary carbinamine moiety. Mechanistic aspects of this reaction are discussed which first involves a reductive N−S cleavage followed by a dearomatizing cyclization.

  在水和溴化锂存在下过量的二碘化钐有效地将未活化的 N-酰化吲哚基亚磺酰基亚胺转化为含有叔卡宾胺部分的多环二氢吲哚衍生物。讨论了该反应的机理方面，首先涉及还原性 N-S 裂解，然后是脱芳构化环化。