1-isothiocyanato-1-methylcyclohexane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: 1-isothiocyanato-1-methylcyclohexane
• 化学式: C₈H₁₃NS
• 分子量: 155.264
• InChiKey: KUOAGUCWTTUXLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氨基甲基环己烷 以 二氯甲烷 为溶剂， 反应 0.41h， 生成 1-isothiocyanato-1-methylcyclohexane
  参考文献：
  名称：

  微波直接合成异硫氰酸酯

  摘要：

  微波技术的应用允许完成从胺类合成异硫氰酸酯的新颖，通用，“绿色”的一锅操作规程。反应易于扩展并且在不消旋手性胺的情况下进行。在这些条件下，中间体二硫代氨基甲酸酯可分解为异硫氰酸酯，而无需任何其他脱硫剂。

  DOI：

  10.1002/ejoc.201900105

文献信息

• T3P® – A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates
  作者：Tadeusz Gajda、Łukasz Janczewski、Anna Gajda、Sebastian Frankowski、Tomasz Goszczyński

  DOI：10.1055/s-0036-1591842

  日期：2018.3

  Abstract A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41–94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P® (propane phosphonic acid anhydride) as a new and efficient desulfurating agent. A number of alkyl, aryl and bifunctional isothiocyanates

  摘要 在母体伯胺或其盐与二硫化碳的两步一锅反应中，以中等至高收率（41-94％）获得了许多烷基，芳基和双官能异硫氰酸酯。与T3P形成二硫代氨基甲酸酯®（丙烷膦酸酐）作为一种新的和有效的脱硫剂。 在母体伯胺或其盐与二硫化碳的两步一锅反应中，以中等至高收率（41-94％）获得了许多烷基，芳基和双官能异硫氰酸酯。与T3P形成二硫代氨基甲酸酯®（丙烷膦酸酐）作为一种新的和有效的脱硫剂。
• Direct, Microwave-Assisted Synthesis of Isothiocyanates
  作者：Łukasz Janczewski、Anna Gajda、Tadeusz Gajda

  DOI：10.1002/ejoc.201900105

  日期：2019.4.16

  Application of microwave technique allowed to accomplish novel, general and “greener” one‐pot protocol for the synthesis of isothiocyanates from amines. Reactions are easily scalable and take place without racemization of chiral amines. Decomposition of the intermediate dithiocarbamates into isothiocyanates proceeds without any additional desulfurating agent under these conditions.

  微波技术的应用允许完成从胺类合成异硫氰酸酯的新颖，通用，“绿色”的一锅操作规程。反应易于扩展并且在不消旋手性胺的情况下进行。在这些条件下，中间体二硫代氨基甲酸酯可分解为异硫氰酸酯，而无需任何其他脱硫剂。
• Synthesis of Medium-Sized Bicyclic Compounds by Intramolecular Cyclization of Cyclic<i>β</i>-Keto Radicals Generated from Cyclopropanols Using Manganese(III) Tris(pyridine-2-carboxylate) and Its Application to Total Synthesis of 10-Isothiocyanatoguaia-6-ene
  作者：Nobuharu Iwasawa、Masahiro Funahashi、Satoshi Hayakawa、Taketo Ikeno、Koichi Narasaka

  DOI：10.1246/bcsj.72.85

  日期：1999.1

  olefinic side chain are oxidized with manganese(III) tris(pyridine-2-carboxylate) to generate cyclic β-keto radicals with ring-expansion. These cyclize intramolecularly, affording bicyclic radical intermediates. The cyclized radicals are trapped with various radical-trapping reagents such as electron-rich or -deficient olefins, tributylstannane and diphenyl diselenide to give the corresponding functionalized

  具有烯烃侧链的双环环丙​​醇被三（吡啶-2-羧酸）锰（III）氧化，生成环状 β-酮基并扩环。这些分子内环化，提供双环自由基中间体。环化的自由基被各种自由基捕获剂捕获，例如富电子或缺电子烯烃、三丁基锡烷和二苯基二硒化物，得到相应的官能化产物。双环产物的立体化学可以通过 MM2 力场计算得到很好的预测。使用该反应实现了异硫氰基倍半萜烯 10-isothiocyanatoguaia-6-ene 的立体选择性全合成。
• Isothiocyanates (ITCs) 1-(Isothiocyanatomethyl)-4-phenylbenzene and 1-Isothiocyanato-3,5-bis(trifluoromethyl)benzene—Aldehyde Dehydrogenase (ALDH) Inhibitors, Decreases Cisplatin Tolerance and Migratory Ability of NSCLC
  作者：Jolanta Kryczka、Jakub Kryczka、Łukasz Janczewski、Anna Gajda、Andrzej Frączyk、Joanna Boncela、Beata Kolesińska、Ewa Brzeziańska-Lasota

  DOI：10.3390/ijms23158644

  日期：——

  One of the main treatment modalities for non-small-cell lung cancer (NSCLC) is cisplatin-based chemotherapy. However, the acquisition of cisplatin resistance remains a major problem. Existing chemotherapy regimens are often ineffective against cancer cells expressing aldehyde dehydrogenase (ALDH). As such, there is an urgent need for therapies targeting ALDH-positive cancer cells. The present study compares the anticancer properties of 36 structurally diverse isothiocyanates (ITCs) against NSCLC cells with the ALDH inhibitor disulfiram (DSF). Their potential affinity to ALDH isoforms and ABC proteins was assessed using AutoDockTools, allowing for selection of three compounds presenting the strongest affinity to all tested proteins. The selected ITCs had no impact on NSCLC cell viability (at tested concentrations), but significantly decreased the cisplatin tolerance of cisplatin-resistant variant of A549 (A549CisR) and advanced (stage 4) NSCLC cell line H1581. Furthermore, long-term supplementation with ITC 1-(isothiocyanatomethyl)-4-phenylbenzene reverses the EMT phenotype and migratory potential of A549CisR to the level presented by parental A549 cells, increasing E-Cadherin expression, followed by decreased expression of ABCC1 and ALDH3A1. Our data indicates that the ALDH inhibitors DSF and ITCs are potential adjuvants of cisplatin chemotherapy.

  非小细胞肺癌（NSCLC）的主要治疗模式之一是以顺铂为基础的化疗。然而，获得顺铂耐药性仍然是一个主要问题。现有的化疗方案通常对表达醛脱氢酶（ALDH）的癌细胞无效。因此，迫切需要针对ALDH阳性癌细胞的治疗方法。本研究比较了36种结构多样的异硫氰酸酯（ITC）与ALDH抑制剂二硫化物（DSF）对NSCLC细胞的抗癌性能。使用AutoDockTools评估它们与ALDH同工酶和ABC蛋白的潜在亲和力，以选择出三种对所有测试蛋白的亲和力最强的化合物。所选的ITC对NSCLC细胞的存活率没有影响（在测试浓度下），但显著降低了顺铂耐药变异株A549CisR和晚期（第四期）NSCLC细胞系H1581的顺铂耐受性。此外，长期补充ITC 1-异硫氰酸甲基-4-苯基苯烷可逆转A549CisR的EMT表型和迁移潜力，使其达到与母细胞A549相同的水平，增加E-Cadherin表达，随后降低ABCC1和ALDH3A1的表达。我们的数据表明，ALDH抑制剂DSF和ITC是顺铂化疗的潜在辅助治疗药物。