exo-Bicyclo<2.2.1>heptan-2-yl isothiocyanate | 18530-33-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: exo-Bicyclo<2.2.1>heptan-2-yl isothiocyanate
• 英文别名: exo-2-norbornyl isothiocyanate；exo-norbornyl isothiocyanate；rac-exo-bicyclo[2.2.1]hept-2-ylisothiocyanate；Norbornyl-(2-endo)-isothiocyanat；exo-2-Norbornyl-isothiocyanat；exo-Bicyclo[2.2.1]heptan-2-yl isothiocyanate；(1R,2R,4S)-2-isothiocyanatobicyclo[2.2.1]heptane
• CAS: 18530-33-1
• 化学式: C₈H₁₁NS
• 分子量: 153.248
• InChiKey: RBGDFYZLQKZUCO-XLPZGREQSA-N

物化性质

• 沸点：
  248.9±7.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  exo-Bicyclo<2.2.1>heptan-2-yl isothiocyanate 在 盐酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 13.0h， 生成 N,N-[3-(4(5)-1H-imidazolyl)pentamethylene]-S-methyl-N'-(exo-2-norbornyl)isothiourea
  参考文献：
  名称：

  Novel Histamine H3 Receptor Antagonists: Synthesis and Evaluation of Formamidine and S-Methylisothiourea Derivatives.

  摘要：

  为了获得一种新型、强效、选择性的组胺H3受体拮抗剂，对众所周知的H3受体拮抗剂硫哌丁胺进行了化学修饰。通过修饰硫过酰胺的硫脲和环己基合成了一系列新的化合物，并使用大鼠大脑皮层质膜通过受体结合测定法测试了 H3 受体亲和力。发现硫过酰胺的硫脲基团可以被碱性部分例如甲脒或S-甲基异硫脲取代。用 1-金刚烷基或外型-2-降冰片基取代硫过酰胺中的环己基可增加对 H3 受体的亲和力。在合成的化合物中，N-(1-金刚烷基)-N',N'-[3-(4(5)-1H-咪唑基)五亚甲基]甲脒3f (AQ0145)表现出最高的H3受体亲和力，具有强效拮抗作用。活动。该化合物对 H3 受体的活性比对 H1 和 H2 受体的活性至少高 1000 倍。

  DOI：

  10.1248/cpb.45.305
• 作为产物：
  描述：

  Norbornyl-(2endo)-thiocyanat 在 (isomerization) 作用下， 以 环丁砜 为溶剂， 生成 exo-Bicyclo<2.2.1>heptan-2-yl isothiocyanate
  参考文献：
  名称：

  Nature of the carbonium ion. IV. .sigma.-Route norbornyl cation from a thiocyanate-isothiocyanate isomerization

  摘要：

  DOI：

  10.1021/ja00708a029

文献信息

• 4,5-Dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators
  申请人：Lange H.M. Josephus

  公开号：US20070142362A1

  公开（公告）日：2007-06-21

  This invention is directed to 4,5-dihydro-(1H)-pyrazole(pyrazoline) derivatives as cannabinoid CB 1 receptor modulators, to pharmaceutical compositions containing these compounds, to methods for the preparation of these compounds, methods for preparing novel intermediates useful for their synthesis, and methods for preparing compositions. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in disorders in which CB 1 receptors are involved, or that can be treated via manipulation of those receptors. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.

  这项发明涉及作为大麻素CB1受体调节剂的4,5-二氢-(1H)-吡唑烯(吡唑啉)衍生物，含有这些化合物的药物组合物，制备这些化合物的方法，用于制备其合成有用的新中间体的方法，以及制备组合物的方法。该发明还涉及这些化合物和组合物的用途，特别是它们在向患者施用以在涉及CB1受体的疾病中实现治疗效果，或者可以通过操纵这些受体来治疗的疾病中的用途。 这些化合物具有通式(I) 其中符号的含义如规范中所述。
• Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas
  作者：C. R. Rasmussen、F. J. Villani, Jr.、L. E. Weaner、B. E. Reynolds、A. R. Hood、L. R. Hecker、S. O. Nortey、A. Hanslin、M. J. Costanzo、E. T. Powell、A. J. Molinari

  DOI：10.1055/s-1988-27605

  日期：——

  An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N′-benzoylthioureas with 5% aqueous sodium hydroxide. Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g., 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.

  制备芳基硫脲的改进方法包括将苯甲酰异硫氰酸酯与苯胺在丙酮中反应，然后用5%氢氧化钠水溶液对生成的N-芳基-N'-苯甲酰硫脲进行去苯甲酰化。双环烷基硫脲和N-(芳烷基)硫脲（例如9H-9-芴基硫脲）可直接由相应的异硫氰酸酯与氨反应制备。
• Synthesis, Antimicrobial and Pharmacological Evaluation of Thioureaderivatives of 4H-1,2,4-triazole
  作者：Anna Bielenica、Ewa Kedzierska、Sylwia Fidecka、Hanna Maluszynska、Barbara Miroslaw、Anna E. Koziol、Joanna Stefanska、Silvia Madeddu、Gabriele Giliberti、Giuseppina Sanna、Marta Struga

  DOI：10.2174/1570180811666141001010044

  日期：2015.2.4

  A group of 4H-1,2,4-triazole-derived thioureas was efficiently prepared and evaluated for antibacterial, antifungal and antiviral activities.The chemical identity of all derivatives was established on the basis of spectral methods. The molecular structures of 10 and 21 were determined by an X-ray crystallography. Compounds with phenyl (1), 3,4-dichlorophenyl (2) and p-methoxyphenyl (3) substituents were the most promising against fungi species. The derivative 12 has proved to be significantly active against CVB-5. The CNS-activity of five new 4H-1,2,4-triazolo-thiourea derivatives 2, 10, 12, 18 and 21 was investigated. The results proved that activity of all tested thiourea compounds may be connected with the serotonergic system. Derivatives 2, 10, 12, 18 acted as inhibitors of the head twitch responses (HTR).The biological activity of 21 was also linked with the endogenous opioid system. The derivative 18 diminished the spontaneous mobility and 10 reduced the amphetamineinduced activity of laboratory animals.

  一批4H-1,2,4-三唑衍生物硫脲被高效制备并评估其抗菌、抗真菌和抗病毒活性。所有衍生物的化学身份基于光谱方法确立。分子结构10和21通过X射线晶体学确定。具有苯基（1）、3,4-二氯苯基（2）和p-甲氧基苯基（3）取代基的化合物对真菌种类最为有效。衍生物12对CVB-5显示出显著活性。研究了五个新的4H-1,2,4-三唑硫脲衍生物2、10、12、18和21的中枢神经系统活性。结果证明所有测试的硫脲化合物的活性可能与血清素系统有关。衍生物2、10、12、18作为头部抽动反应（HTR）的抑制剂。21的生物活性也与内源性阿片系统相关。衍生物18降低了自发活动性，10减少了实验室动物的安非他命诱导活动。
• Comparison of Large-Scale Routes to Manufacture Chiral <i>exo</i>-2-Norbornyl Thiourea
  作者：Seb Caille、Jerome Boni、Geoffrey B. Cox、Margaret M. Faul、Pilar Franco、Saab Khattabi、Liane M. Klingensmith、Jay F. Larrow、James K. Lee、Michael J. Martinelli、Larry M. Miller、George A. Moniz、Kenichi Sakai、Jason S. Tedrow、Karl B. Hansen

  DOI：10.1021/op9002328

  日期：2010.1.15

  Two routes aimed at the manufacture of chiral exo-2-norbornyl thiourea (1) on large scale are described. The first approach involves live chemical steps and hinges on a classical resolution via diastereomeric salt formation. The synthesis utilizes amine 2 as the resolution handle. The second approach includes two chemical steps and a chiral chromatography of (+/-)-1. Despite the larger initial investment necessary to acquire the chiral stationary phase used in the chromatographic approach, the shorter reaction sequence and efficiency of the chromatographic separation make the second route a more attractive option tor long-term applications.
• Nature of the carbonium ion. I. The .pi.-route to a norbornyl cation from a thiocyanate-isothiocyanate isomerization
  作者：Langley A. Spurlock、Walter G. Cox

  DOI：10.1021/ja01039a023

  日期：1969.5