4,6-dibromoolivetol | 78463-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,6-dibromoolivetol
• 英文别名: 4,6-dibromo-5-pentylbenzene-1,3-diol；4,6-Dibromo Olivetol
• CAS: 78463-34-0
• 化学式: C₁₁H₁₄Br₂O₂
• 分子量: 338.039
• InChiKey: INKUHDWQKDJMNG-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  382.5±37.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-dibromoolivetol 在 magnesium sulfate 、 对甲苯磺酸 、 三乙胺 、 sodium sulfite 、 维生素 C 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 大麻二酚
  参考文献：
  名称：

  Design of Negative and Positive Allosteric Modulators of the Cannabinoid CB₂ Receptor Derived from the Natural Product Cannabidiol

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00561
• 作为产物：
  描述：

  5-n-amyl-2-bromocyclohex-2-ene-3-ol-1-one 以10%的产率得到
  参考文献：
  名称：

  CHANDRASEKHARAN, V.;UNNIKRISHNAN, P.;SHAH, G. D.;BHATTACHARYYA, S. C., INDIAN J. CHEM., 1980, 19, N 12, 1052-1055

  摘要：

  DOI：

文献信息

• [EN] SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION<br/>[FR] SYNTHÈSE ET PURIFICATION DE CANNABIGÉROL ET SON UTILISATION
  申请人：SYMRISE AG

  公开号：WO2020249184A1

  公开（公告）日：2020-12-17

  The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.

  本发明涉及一种从反应混合物中生产大麻生酚并对其进行纯化的方法。本发明还涉及大麻生酚在化妆品中的应用，用于抑制酪氨酸酶活性和/或减少皮肤中黑色素的产生，特别是用于减少皮肤的色素沉着，优选用于改善皮肤在色素沉着过多、雀斑或白癜风等情况下的外观。此外，本发明涉及大麻生酚用于治疗方法，用于抑制皮肤中酪氨酸酶活性和/或减少黑色素的产生，特别是用于治疗和/或预防恶性皮肤疾病，特别是皮肤癌的治疗方法。
• PROCESS FOR THE PRODUCTION OF CANNABIDIOL AND DELTA-9-TETRAHYDROCANNABINOL
  申请人：NORAMCO, INC.

  公开号：US20170008868A1

  公开（公告）日：2017-01-12

  The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

  本公开涉及制备大麻二酚化合物或其衍生物。大麻二酚化合物或其衍生物可通过选择适当的和取代的双卤代橄榄酮或其衍生物与适当选择的和取代的环烯烃进行酸催化反应来制备，从而产生双卤代大麻二酚化合物或其衍生物。双卤代大麻二酚化合物或其衍生物可高产率、高立体选择性或两者兼具地制备。然后，它可以在还原条件下转化为大麻二酚化合物或其衍生物。
• [EN] PROCESSES FOR THE PREPARATION OF HALOGENATED DIHYDROXYBENZENE COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS DIHYDROXYBENZÈNE HALOGÉNÉS
  申请人：PURISYS LLC

  公开号：WO2020243588A1

  公开（公告）日：2020-12-03

  The present disclosure relates to the preparation of halogenated dihydroxybenzene compounds with high yield, selectivity and purity. The compounds are useful, among other things, in the synthesis of cannabinoids and cannabinoid-type compounds.

  本公开涉及制备高产率、选择性和纯度的卤代二羟基苯化合物。该化合物在合成大麻素和类大麻素化合物等方面具有实用价值。
• [EN] CRYSTALLINE CANNABIGEROL<br/>[FR] CANNABIGÉROL CRISTALLIN
  申请人：PURISYS LLC

  公开号：WO2020252369A1

  公开（公告）日：2020-12-17

  The application relates to crystalline cannabigerol comprising at least one X-ray powder diffraction peak selected from the group consisting of 4.73°, 9.52°, 14.30°, and 23.93° 2Θ (each ± 0.20° 2Θ), to methods of making the crystalline cannabigerol and its medical uses.

  该申请涉及到晶体型大麻酚（cannabigerol）的制备方法，其中晶体型大麻酚至少包含以下所选组中的一个X射线粉末衍射峰：4.73°、9.52°、14.30°和23.93° 2Θ（每个±0.20° 2Θ），以及晶体型大麻酚的医疗用途。
• Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
  申请人：NORAMCO, INC.

  公开号：US10059683B2

  公开（公告）日：2018-08-28

  The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

  本公开涉及制备大麻二酚化合物或其衍生物。该大麻二酚化合物或其衍生物可以通过适当选择和取代的二卤代奥利维托或其衍生物与适当选择和取代的环烯烃进行酸催化反应来制备，从而产生二卤代大麻二酚化合物或其衍生物。该二卤代大麻二酚化合物或其衍生物可以高产率、高立体特异性或两者兼具地制备。然后可以在还原条件下将其转化为大麻二酚化合物或其衍生物。