(E)-N′-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide | 17336-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-N′-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide
• 英文别名: (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide；tetralone tosyl hydrazone；N'-[(1E)-3,4-dihydronaphthalen-1(2H)-ylidene]-4-methylbenzenesulfonohydrazide；N-[(E)-3,4-dihydro-2H-naphthalen-1-ylideneamino]-4-methylbenzenesulfonamide
• CAS: 17336-59-3
• 化学式: C₁₇H₁₈N₂O₂S
• 分子量: 314.408
• InChiKey: KQNWJQOEQKMDHH-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N′-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide 在 potassium peroxomonosulphate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.2h， 以90%的产率得到3,4-二氢-1(2H)-萘酮
  参考文献：
  名称：

  Bose, D. Subhas; Vanajatha; Srinivas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 7, p. 835 - 836

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 生成 (E)-N′-(3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  GRANDI R.; MARCHESINI A.; PAGNONI U. M.; TRAVE R., J. ORG. CHEM. , 1976, 41, NO 10, 1755-1758

  摘要：

  DOI：

文献信息

• Pyrrolo-imidazo[1,2-<i>a</i>]pyridine Scaffolds through a Sequential Coupling of <i>N</i>-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application
  作者：Kena Zhang、Abderrahman El Bouakher、Helene Levaique、Jerome Bignon、Pascal Retailleau、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.joc.9b02018

  日期：2019.11.1

  of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(arylvinyl)imidazo[1,2-a]pyridine derivatives. Optimization of Cadogan-reductive conditions allowed the conversion of the obtained nitro derivative to a new scaffold of the type 3-aryl-

  描述了构建3-苯基-1H-吡咯并咪唑并[1,2-a]吡啶骨架的新策略。反应从N-甲苯磺酰hydr与2-氯-3-硝基咪唑并[1,2-a]吡啶之间的偶联开始，导致3-硝基-2-（芳基乙烯基）咪唑并[1,2-a]吡啶衍生物的形成。Cadogan还原条件的优化允许将获得的硝基衍生物转化为新的3-芳基-1H-吡咯并咪唑并[1,2-a]吡啶型支架。该方法在面向多样性的合成中提供了对新文库的快速访问，该合成旨在以有效的方式生成具有大结构多样性的小分子。筛选出新产生的化合物的生物活性后，鉴定出了一种新的有前途的化合物5cc，
• Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles
  作者：Bang-Hong Zhang、Lin-Sheng Lei、Si-Zhan Liu、Xue-Qing Mou、Wei-Ting Liu、Shao-Hua Wang、Jie Wang、Wen Bao、Kun Zhang

  DOI：10.1039/c7cc04610c

  日期：——

  A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.

  已成功开发了甲苯磺酰肼与2-（二甲氨基）丙二腈的Zn（OTf）2促进的环化反应，为合成取代的1-tosyl-1 H-吡唑提供了有效的策略。
• Kinetic Resolution of Allylic Alcohols Using a Chiral Phosphine Catalyst
  作者：Edwin Vedejs、James A. MacKay

  DOI：10.1021/ol006923g

  日期：2001.2.1

  [GRAPHICS]The kinetic resolution of racemic allylic alcohols 3, 6, and 12-17 has been explored using the PBO catalyst 7 for activation of isobutyric anhydride. Trisubstituted allylic alcohols (12-15; 17) are the best substrates and react with an enantiaselectivity of s = 32-82 at -40 degrees C.
• I₂–TBHP-Catalyzed Oxidative Cross-Coupling of <i>N</i>-Sulfonyl Hydrazones and Isocyanides to 5-Aminopyrazoles
  作者：Gopal Chandru Senadi、Wan-Ping Hu、Ting-Yi Lu、Amol Milind Garkhedkar、Jaya Kishore Vandavasi、Jeh-Jeng Wang

  DOI：10.1021/acs.orglett.5b00398

  日期：2015.3.20

  I-2-TBHP-catalyzed oxidative cross coupling of N-sulfonyl hydrazones with isocyanides has been realized for the synthesis of 5-aminopyrazoles through formal [4 + 1] annulation via in situ azoalkene formation. Notable features are the metal/alkyne-free strategy, C-C and C-N bond formation, atom economy, catalytic I-2, broad functional group tolerance, good reaction yields, shorter time, and also applicability to one-pot methodology.
• Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas’ disease
  作者：Rogelio Siles、Shen-En Chen、Ming Zhou、Kevin G. Pinney、Mary Lynn Trawick

  DOI：10.1016/j.bmcl.2006.05.041

  日期：2006.8

  A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively. (c) 2006 Elsevier Ltd. All rights reserved.