(E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol | 958728-39-7

• 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: (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol
• 英文别名: 4-[(2E)-3,7-dimethylocta-2,6-dienyl]benzene-1,3-diol
• CAS: 958728-39-7
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: RGUSQESFCCLNEG-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 在 sodium hydride 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.33h， 生成 3-[(E)-5-[2,4-bis(phenylmethoxymethoxy)phenyl]-3-methylpent-3-enyl]-2,2-dimethyloxirane
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102
• 作为产物：
  描述：

  香叶醇 、 间苯二酚 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以11.9%的产率得到(E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol
  参考文献：
  名称：

  SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS

  摘要：

  DOI：

  10.4067/s0717-97072013000200033

文献信息

• In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands
  作者：María Chavez、Mauricio Soto、Franco Cimino、Andrés Olea、Luis Espinoza、Katy Díaz、Lautaro Taborga

  DOI：10.3390/ijms19061601

  日期：——

  A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of Phytophthora cinnamomi. The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one

  一系列新的和已知的香叶基酚/甲氧基苯酚衍生物已在体外进行了测试，作为肉桂疫霉菌的菌丝体生长抑制剂。被测化合物的活性与芳环上取代基的性质，数量和位置相关。结果表明，活性最高的香叶基衍生物是具有两个与芳环相连的羟基（或一个-OH和一个-OCH3）的衍生物。有趣的是，这些衍生物的活性与常用的商业杀菌剂Metalaxil®相同。因此，我们的结果表明，这些化合物中的某些可能因其潜在用途作为抗肉桂粉虱的杀真菌剂而具有农业意义。讨论了结构对杀真菌剂活性的影响，同时讨论了芳香环和香叶基侧链上的电子分布。所有测试的化合物都是通过香叶醇和相应的苯酚的直接偶联合成的。有趣的是，通过增加反应时间获得了新的二geranylated衍生物。
• [EN] CATALYTIC CANNABIGEROL PROCESSES AND PRECURSORS<br/>[FR] PROCÉDÉS ET PRÉCURSEURS CATALYTIQUES DE CANNABIGÉROL
  申请人：KARE CHEMICAL TECH INC

  公开号：WO2021195751A1

  公开（公告）日：2021-10-07

  The present disclosure relates to cannabigerol sulfonate esters and processes for their use to prepare cannabigerol (CBG) and related compounds, including cannabigerobutol (CBGB), cannabigerovarin (CBGV), and cannabigerophorbol (CBGP). In a preferred embodiment, the cannabigerol sulfonate ester is (E)-4-(3, 7-5 dimethylocta-2,6-dienyl)-3,5-bis(trimetbylsilyloxy)phenyl trifluoromethanesulfonate. In a preferred process, the trifluoromethansulfonate leaving group is replaced by an alkyl group. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabigerol and related compounds from the cannabigerol sulfonate esters.

  本公开涉及大麻酚磺酸酯及其用于制备大麻酚（CBG）和相关化合物的过程，包括大麻酚丁醇（CBGB）、大麻酚瓦林（CBGV）和大麻酚酚醇（CBGP）。在一种首选实施方式中，大麻酚磺酸酯是（E）-4-（3,7-5二甲基辛二烯基）-3,5-双（三甲基硅氧基）苯基三氟甲磺酸酯。在一种首选过程中，三氟甲磺酸酯离去基被烷基取代。本公开还涉及催化剂和催化过程的使用，用于从大麻酚磺酸酯制备大麻酚和相关化合物。
• Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against Botrytis cinerea
  作者：Mauricio Soto、Ana Estevez-Braun、Ángel Amesty、Julia Kluepfel、Susana Restrepo、Katy Diaz、Luis Espinoza、Andrés F. Olea、Lautaro Taborga

  DOI：10.3390/molecules26226815

  日期：——

  work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against B. cinerea has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with p-toluenesulfonic acid

  灰葡萄孢是一种普遍存在的真菌，​​影响数百种植物，给园艺和水果业造成经济损失。寻找新的抗真菌药物是当前人们关注的问题。因此，在这项工作中，合成了一系列烷基侧链已水合的香叶基化酚，并评估了它们针对灰霉病菌的活性。苯酚和香叶醇的偶联是在微波辐射下完成的，在最短的反应时间内获得了最高的反应产率。侧链的水合在二恶烷中以键合的对甲苯磺酸聚合物作为催化剂进行。使用生长抑制测定测试所有合成的化合物针对灰霉病菌的效果并测定EC 50值。结果表明，活性取决于酚环中官能团的数量和性质以及香叶基链的水合程度。最活跃的化合物是1,4-二氢醌，其烷基链末端带有一个羟基。分子对接研究的结果表明，酚环和烷基链中的羟基对于化合物与活性位点的结合非常重要，并且实验的抗真菌活性与结合中可以形成的氢键的数量相关。地点。
• Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents
  作者：Lautaro Taborga、Maximiliano Sortino、Héctor Carrasco、Estefanía Butassi、Susana Zacchino、Luis Espinoza

  DOI：10.1016/j.fct.2017.05.027

  日期：2017.11

  antifungal activities than those of series (ii). In addition, within group (i) all compounds showed better activities against C. neoformans than against C. albicans which can be easily verified by comparing MIC100 or MIC50 of each compound against both fungi. Di- (10 and 11) and tri-hydroxy (3 and 4) compounds showed significant anti-cryptoccocal activity, being 3, 10 and 11 highly active with MIC100 or MIC50

  评价了二十四种线性香叶基酚对ATCC的抗真菌特性以及白色念珠菌和新隐球菌的临床分离株。为了分析它们的抗真菌行为，将这些化合物分为两个系列：（i）在苯环上仅具有一个香叶基取代基的化合物和（ii）在苯环上具有两个香叶基部分的化合物。结果表明，系列（i）的化合物具有比系列（ii）更好的抗真菌活性。另外，在组（i）中，所有化合物对新孢子虫均显示出比对白色念珠菌更好的活性，这可以通过比较每种化合物对两种真菌的MIC100或MIC50来容易地证实。二（10和11）和三羟基（3和4）化合物显示出显着的抗隐球菌活性，为3，与标准药物两性霉素B相似，MIC100或MIC50 = 3.9μg/ mL时具有高活性的10和11。此外，当评估化合物6、10和11对HDF细胞系（人真皮成纤维细胞）的毒性时， IC50值> 100μM，被认为对细胞无毒。这表明所分析化合物的毒性对真菌具有选择性，这使其成为未来药物开发中非常有吸引力的家族。
• Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A
  作者：Joseph J. Topczewski、John G. Kodet、David F. Wiemer

  DOI：10.1021/jo1022102

  日期：2011.2.4

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.