cannabiorcol | 19825-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: cannabiorcol
• 英文别名: 3,6,6,9-tetramethyl-6H-benzo[c]chromen-1-ol；3,6,6,9-tetramethylbenzo[c]chromen-1-ol
• CAS: 19825-73-1
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: XWIWWMIPMYDFOV-UHFFFAOYSA-N

物化性质

• 沸点：
  431.6±44.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cannabiorcol 、 4-硝基苯甲酰氯 在 吡啶 作用下， 生成 4-nitro-benzoic acid-(3,6,6,9-tetramethyl-6H-benzo[c]chromen-1-yl ester)
  参考文献：
  名称：

  31.印度大麻。第六部分 蒲乐酮与烷基间苯二酚的缩合反应。大麻酚和具有大麻活性的产品的新合成

  摘要：

  DOI：

  10.1039/jr9410000137
• 作为产物：
  描述：

  3,5-二羟基甲苯 在 三氟化硼乙醚 、 碘 、 magnesium sulfate 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 22.0h， 生成 cannabiorcol
  参考文献：
  名称：

  源自大麻的稀有大麻素的合成策略

  摘要：

  建立并优化了八种关键大麻素的有效合成。主要的大麻素如大麻酚 (CBG-C 5 ) 和大麻二酚 (CBD-C 5 ) 是由橄榄醇通过区域选择性缩合制备的。CBD 的进一步处理导致 Δ 9 -四氢大麻酚 (THC-C 5 )、Δ 8 -异四氢大麻酚 ( iso -THC-C 5 ) 和大麻酚 (CBN-C 5 )。或者，橄榄醇和柠檬醛之间的 [3 + 3] 环化产生了少量大麻素大麻色素 (CBC-C 5 )，其转化为两个非常罕见的多环，大麻二环醇 (CBL-C 5) 和大麻素 (CBT-C 5 )，在一锅反应中。最后，通过利用间苯二酚和两种酚类类似物对所有八种合成进行了扩展，通过简便的合成策略实现了具有 30 多种化合物的大麻素组。

  DOI：

  10.1021/acs.jnatprod.2c00155

文献信息

• [EN] METHOD FOR THE METAL-FREE PREPARATION OF A BIARYL BY A PHOTOSPLICING REACTION AND THEIR USES<br/>[FR] PROCÉDÉ DE PRÉPARATION SANS MÉTAL D'UN BIARYLE PAR RÉACTION DE PHOTOCOLLAGE ET UTILISATIONS ASSOCIÉES
  申请人：LEIBNIZ INST FUER NATURSTOFF FORSCHUNG UND INFEKTIONSBIOLOGIE E V HANS KNOELL INST HKI

  公开号：WO2019101679A1

  公开（公告）日：2019-05-31

  The present invention relates to a method for the metal-free preparation of a biaryl compound by a photosplicing reaction and its use in the preparation of chemical compounds, preferably of active ingredients e.g. in the fields of pharmaceuticals and agrochemicals. In particular, it refers to a method for the regiocontrolled preparation of a biaryl compound of formula (I): Ar-Ar' by photochemically reacting a precursor compound of formula (II): Ar-L-Ar' to form a biaryl compound of general formula: Ar-L-Ar' (II) → Ar-Ar' (I) wherein Ar and Ar', independently of each other, represent an unsubstituted or substituted C6-C20 aryl group or a heteroaryl group with 5–20 ring atoms selected from carbon, nitrogen, oxygen and sulfur, and L represents a group –X–Y–Z– as defined herein. The biaryl compounds are generally suitable as intermediates or key building blocks in a very broad spectrum of organic chemical syntheses and their respective utilities. Their use within the field of synthesis of active ingredients is an aspect of the invention, and their use in the preparation of pharmaceutically active ingredients is particularly preferred.

  本发明涉及一种通过光切割反应无金属制备联芳烃化合物的方法，以及其在化学化合物制备中的用途，特别是在制药和农药领域中的活性成分的制备中的用途。具体而言，它涉及一种通过光化学反应化学前体化合物（II）：Ar-L-Ar'与形成一般式的联芳烃化合物（II）→Ar-Ar'（I）反应，从而实现联芳烃化合物（I）的区域控制制备的方法，其中Ar和Ar'分别表示未取代或取代的C6-C20芳基或由碳、氮、氧和硫选择的5-20个环原子的杂芳基，L表示如本文所定义的一个组-X-Y-Z-。这些联芳烃化合物通常适用于有机化学合成的广泛领域中的中间体或关键构建块，以及它们各自的用途。它们在活性成分合成领域中的用途是本发明的一个方面，它们在制备药用活性成分中的用途尤为理想。
• SARs for the Antiparasitic Plant Metabolite Pulchrol. 3. Combinations of New Substituents in A/B-Rings and A/C-Rings
  作者：Paola Terrazas、Efrain Salamanca、Marcelo Dávila、Sophie Manner、Alberto Gimenez、Olov Sterner

  DOI：10.3390/molecules26133944

  日期：——

  The natural products pulchrol and pulchral, isolated from the roots of the Mexican plant Bourreria pulchra, have previously been shown to possess antiparasitic activity towards Trypanosoma cruzi, Leishmania braziliensis and L. amazonensis, which are protozoa responsible for Chagas disease and leishmaniasis. These infections have been classified as neglected diseases, and still require the development of safer and more efficient alternatives to their current treatments. Recent SARs studies, based on the pulchrol scaffold, showed which effects exchanges of its substituents have on the antileishmanial and antitrypanosomal activity. Many of the analogues prepared were shown to be more potent than pulchrol and the current drugs used to treat leishmaniasis and Chagas disease (miltefosine and benznidazole, respectively), in vitro. Moreover, indications of some of the possible interactions that may take place in the binding sites were also identified. In this study, 12 analogues with modifications at two or three different positions in two of the three rings were prepared by synthetic and semi-synthetic procedures. The molecules were assayed in vitro towards T. cruzi epimastigotes, L. braziliensis promastigotes, and L. amazonensis promastigotes. Some compounds had higher antiparasitic activity than the parental compound pulchrol, and in some cases even benznidazole and miltefosine. The best combinations in this subset are with carbonyl functionalities in the A-ring and isopropyl groups in the C-ring, as well as with alkyl substituents in both the A- and C-rings combined with a hydroxyl group in position 1 (C-ring). The latter corresponds to cannabinol, which indeed was shown to be potent towards all the parasites.

  墨西哥植物 Bourreria pulchra 的根部中分离出的天然产物 pulchrol 和 pulchral 已被证明具有抗原虫活性，对克氏锥虫、巴西利亚利什曼虫和亚马逊利什曼虫等原虫引起的光谷病和利什曼病具有活性。这些感染已被归类为被忽视的疾病，仍需要开发更安全、更有效的替代治疗方法。最近的结构活性关系研究，基于 pulchrol 结构骨架，展示了其取代基之间交换对抗利什曼虫和抗克氏锥虫活性的影响。许多制备的类似物显示比 pulchrol 和目前用于治疗利什曼病和光谷病的药物（分别为米尔特霉素和苯硝唑）更具有潜力。此外，还发现了可能发生在结合位点中的一些相互作用迹象。在这项研究中，通过合成和半合成方法制备了在两个或三个不同位置的两个三环中进行修饰的12个类似物。这些分子在体外对克氏锥虫的梭形体、巴西利亚利什曼虫的梭形体和亚马逊利什曼虫的梭形体进行了测定。一些化合物的抗原虫活性比母体化合物 pulchrol 更高，甚至有时比苯硝唑和米尔特霉素还要高。在这个子集中效果最好的组合是 A 环中的酮功能基和 C 环中的异丙基，以及 A 和 C 两环中的烷基取代基与位置 1（C 环）的羟基结合。后者对所有寄生虫都显示出了强大的活性，这对应于大麻酚。
• One-Pot Total Synthesis of Cannabinol via Iodine-Mediated Deconstructive Annulation
  作者：Diego Caprioglio、Daiana Mattoteia、Alberto Minassi、Federica Pollastro、Annalisa Lopatriello、Eduardo Muňoz、Orazio Taglialatela-Scafati、Giovanni Appendino

  DOI：10.1021/acs.orglett.9b02258

  日期：2019.8.2

  coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their in situ deconstructive annulation to benzo[c]chromenes. This process was applied to a total synthesis of cannabinol (CBN, 5) and to its molecular editing.

  大麻素（CBC，3）的热降解主要受阳离子反应的影响，而不是模型化合物中观察到的周环重排。这些差异的合理化激发了工艺的发展，该工艺在芳构化驱动的单个操作步骤中将柠檬醛和烷基间苯二酚缩合为高异戊二烯基色烯，并将它们原位解构性环化为苯并[ c ]色烯。此过程应用于大麻酚（CBN，5）的全合成及其分子编辑。
• TEST KIT FOR THE QUANTITATIVE DETERMINATION OF NARCOTIC DRUGS
  申请人：CHIRON AS

  公开号：US20150204893A1

  公开（公告）日：2015-07-23

  A test kit for the quantitative determination of narcotic drugs comprising (A) series of sealed vessels, each vessel containing a deuterium free isotopologue of a narcotic drug in exactly defined concentrations and quantities, wherein the isotopologue differs from vessel to vessel and—wherein the quantities of the isotopologue differ from vessel to vessel or are the same for all vessels; and/or (B) series of sealed vessels, each vessel containing in exactly defined concentrations and quantities the same isotopologue in quantities which differ from vessel to vessel; wherein the free isotopologues are selected from narcotic drugs; prodrugs, salts, solvates, hydrates and polymorphs and contain at least three stable isotopes selected from the group consisting of 13 C, 15 N and 18 O in the molecule with a degree of labeling of at least 95 mol-%; the use of the test kit and a method for quantitatively determining narcotic drugs.

  一种用于定量测定麻醉药物的检测试剂盒，包括（A）一系列密封容器，每个容器中含有一种去氘同位素麻醉药物，其浓度和数量均被精确定义，其中同位素从容器到容器不同，同位素的数量在容器到容器之间不同或对所有容器都相同；和/或（B）一系列密封容器，每个容器中含有相同的同位素，其浓度和数量被精确定义，数量在容器到容器之间不同；其中自由同位素选自麻醉药物、前药、盐、溶剂、水合物和多晶形，并且在分子中至少包含三种稳定同位素，所述稳定同位素选自13C、15N和18O，其标记度至少为95摩尔％；使用该检测试剂盒和一种定量测定麻醉药物的方法。
• [EN] CATALYTIC CANNABINOL SYNTHESIS AND PRECURSORS<br/>[FR] SYNTHÈSE ET PRÉCURSEURS CATALYTIQUES DE CANNABINOL
  申请人：KARE CHEMICAL TECH INC

  公开号：WO2022187935A1

  公开（公告）日：2022-09-15

  Cannabinol (CBN) is a minor cannabinoid found in the cannabis plant and there is significant interest in exploring CBN for pharmaceutical applications. It is currently being investigated for treating glaucoma, sleep disorders and skin inflammations. Several synthetic approaches for CBN have been described in the prior art, however methods are still limited in scope because of the harsh reaction conditions, number of steps involved, low yields and extensive purifications that are generally required. The present disclosure relates to new cannabinol precursor compounds and processes to prepare cannabinol compounds. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinol compounds from the cannabinol precursors.

  大麻素CBN是大麻植物中的一种次要大麻素，目前有着在药学应用方面探索的重要意义。它目前正在研究用于治疗青光眼、睡眠障碍和皮肤炎症。先前的文献中已经描述了几种CBN的合成方法，但由于反应条件苛刻、步骤繁多、产率低和通常需要进行广泛净化等原因，这些方法的范围仍然受到限制。本公开涉及新的大麻酚前体化合物和制备大麻酚化合物的方法。本公开还涉及使用催化剂和催化过程从大麻酚前体化合物制备大麻酚化合物的方法。