1-isothiocyanato-1,2,3,4-tetrahydronaphthalene | 58490-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-isothiocyanato-1,2,3,4-tetrahydronaphthalene
• CAS: 58490-93-0
• 化学式: C₁₁H₁₁NS
• 分子量: 189.281
• InChiKey: ZQBGMSSJXYYZET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-isothiocyanato-1,2,3,4-tetrahydronaphthalene 生成 1-Ethyl-3-(1,2,3,4-tetrahydro-1-naphthyl)-thiourea
  参考文献：
  名称：

  Ureidotetralin compounds

  摘要：

  本发明涉及尿素四氢萘化合物及其衍生物以及所选的对映体。本发明还涉及用作动物生长调节剂和/或除草剂的所述化合物的制备方法。

  公开号：

  US03953506A1
• 作为产物：
  描述：

  四酮-1-肟 在 sodium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 丙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 1-isothiocyanato-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants☆

  摘要：

  A series of thiourea derivatives (7-23, 25-27) of 1-aminotetrahydronaphthalene (4) and 1-amino-2-hydroxytetrahydronaphthalene (5) were synthesized in single pot in 48-90% yield and evaluated for their anorexigenic activity. Among them compounds 10, 14 15, 16 and 22 exhibited significant anorexigenic activity without any antidepressant effect and provided a new structural lead for appetite suppressants. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.039

文献信息

• Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines
  作者：Jiao Yu、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1002/anie.201710186

  日期：2017.12.22

  The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o‐phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one‐pot process

  描述了在温和条件下由二氟卡宾生成的硫代羰基氟化物与各种胺的反应。仲胺，伯胺和邻苯二胺分别转化为硫代氨基甲酰氟，异硫氰酸酯和二氟甲基硫代杂环。硫氨甲酰氟通过一锅法进一步转化为三氟甲基化胺。硫代羰基氟化物在原位生成，并在温和条件下在一锅中迅速完全转化；因此，不需要特殊的安全预防措施。
• Isothiocyanates from Tosyl Chloride Mediated Decomposition of in Situ Generated Dithiocarbamic Acid Salts
  作者：Rince Wong、Sarah J. Dolman

  DOI：10.1021/jo070246n

  日期：2007.5.1

  A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.

  据报道，由烷基胺和芳基胺制备异硫氰酸酯的简便通用方法。该方法依赖于甲苯磺酰氯介导的二硫代氨基甲酸盐的分解，该二硫代氨基甲酸盐是通过用二硫化碳和三乙胺处理胺而原位产生的。利用该方案，我们以中等至极好的收率制备了19-烷基异硫氰酸酯和芳基异硫氰酸酯。
• Metabolic Fate of the Isocyanide Moiety: Are Isocyanides Pharmacophore Groups Neglected by Medicinal Chemists?
  作者：Ubaldina Galli、Gian Cesare Tron、Beatrice Purghè、Giorgio Grosa、Silvio Aprile

  DOI：10.1021/acs.chemrestox.9b00504

  日期：2020.4.20

  idea, the hepatic metabolism of six model isocyanides was investigated. Aromatic and primary isocyanides turned out to be unstable and metabolically labile, but secondary and tertiary isocyanides resisted metabolization, showing, in some cases, cytochrome P450 inhibitory properties. The potential therefore exists for the secondary and tertiary isocyanides to qualify them as pharmacophore groups, in

  尽管从陆地真菌和细菌以及海洋生物中分离出了数百种生物活性异氰化物，但从药用化学的角度来看，迄今为止，异氰化物的功能很少受到关注。异氰酸酯在化学和代谢上不稳定的普遍信条将生物活性研究局限于其防污性能和技术应用。为了证实或反驳这一想法，研究了六种模型异氰酸酯的肝代谢。芳香族和初级异氰酸酯不稳定且代谢不稳定，但次级和叔异氰酸酯抗代谢，在某些情况下显示出细胞色素P450的抑制特性。因此，存在仲异氰酸酯和叔异氰酸酯使其成为药效团基团的潜力，
• Electrochemical Benzylic C(sp³)–H Isothiocyanation
  作者：Shanxue Zhang、Yufeng Li、Tao Wang、Ming Li、Lirong Wen、Weisi Guo

  DOI：10.1021/acs.orglett.2c00415

  日期：2022.3.4

  Selective C(sp3)–H isothiocyanation represents a significant strategy for the synthesis of isothiocyanate derivatives. We report herein an electrochemical benzylic isothiocyanation in a highly chemo- and site-selective manner under external oxidant-free conditions. The high chemoselectivity is attributed to the facile in situ isomerization of benzylic thiocyanates to isothiocyanates. Notably, the method

  选择性 C(sp 3 )-H 异硫氰化代表了合成异硫氰酸酯衍生物的重要策略。我们在此报告了在外部无氧化剂条件下以高度化学和位点选择性方式进行的电化学苄基异硫氰化反应。高化学选择性归因于苄基硫氰酸酯容易原位异构化为异硫氰酸酯。值得注意的是，该方法具有较高的官能团相容性，适用于生物活性分子的后期功能化。
• Novel Use
  申请人：Tiden Anna-Karin

  公开号：US20080096929A1

  公开（公告）日：2008-04-24

  There is disclosed the use of a compound of formula (I), (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  本发明揭示了一种使用式(I)化合物及其药学上可接受的盐在制备药物方面的应用，用于治疗或预防抑制髓过氧化物酶(MPO)酶有益的疾病或病症。本发明还揭示了某些新型式(I)化合物及其药学上可接受的盐，以及它们的制备过程。式(I)化合物是MPO抑制剂，因此在治疗或预防神经炎性疾病方面特别有用。