(2,6,6-trimethylcyclohex-1-enyl)phenylmethanol | 911850-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,6,6-trimethylcyclohex-1-enyl)phenylmethanol
• 英文别名: phenyl(2,6,6-trimethylcyclohex-1-enyl)methanol；Phenyl-(2,6,6-trimethylcyclohexen-1-yl)methanol
• CAS: 911850-37-8
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: WTIIBDQNPFAPPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,6,6-trimethylcyclohex-1-enyl)phenylmethanol 在 吡啶 、 2,6-二叔丁基吡啶 、 戴斯-马丁氧化剂 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 2,3,4,4a-tetrahydro-1,1,4a-trimethyl-1H-fluoren-9-yl trifluromethanesulfonate
  参考文献：
  名称：

  Synthesis of Taiwaniaquinoids via Nazarov Triflation

  摘要：

  A unified approach toward the taiwaniaquinoids that has yielded four natural products is described. A new variant of the Nazarov reaction with concomitant formation of an enol triflate serves as one of the key steps, considerably shortening the synthetic scheme and providing a general entry into this class of bioactive natural products.

  DOI：

  10.1021/ja062505g
• 作为产物：
  描述：

  1-吡咯烷羧酸,3-[[(3-溴苯基)氨基]甲基]-,1,1-二甲基乙基酯 、 苯基溴化镁 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2,6,6-trimethylcyclohex-1-enyl)phenylmethanol
  参考文献：
  名称：

  潜在的新型细胞凋亡剂的设计和合成：含有紫苏醇和新型受限视黄醇的混合化合物

  摘要：

  通过将紫苏醇添加到由 DCC（N , N'-二环己基碳二亚胺）促进的活化羧酸（类维生素A）中，合成了含有紫苏醇的新型类维生素A 1 – 3。以良好的收率（78-82%）获得了一组结构和功能多样的类维生素A紫苏醇衍生物。我们的实验室目前正在对这些新型混合化合物（含有类维生素A和紫苏醇）进行生物学评估。

  DOI：

  10.1016/j.tetlet.2010.01.003

文献信息

• Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H
  作者：Badrinath N. Kakde、Subhadip De、Dhananjay Dey、Alakesh Bisai

  DOI：10.1039/c3ra41497c

  日期：——

  A formal synthesis of diterpenoids viz. the taiwaniaquinoids (±)-dichroanone (1a) and (±)-taiwaniaquinone H (1b) possessing an all carbon quaternary stereocenter has been reported. The key step involves a metal triflate-catalyzed cyclization of arylvinylcarbinols, prepared from β-cyclocitral. The reaction possibly follows a stepwise mechanism via the intermediacy of arylallyl carbocationic species

  正式合成二萜类化合物。据报道，具有全碳四元立体中心的台湾醌类（±）-二氢蒽酮（1a）和（±）-台湾醌H（1b）。关键步骤涉及由三氟甲磺酸酯催化的由β-环柠檬醛制得的芳基乙烯基甲醇的环化反应。该反应可能通过芳基烯丙基碳阳离子物质的中间体遵循逐步机理。
• A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Eduardo Cabrera、Esteban Alvarez、Ramón Alvarez-Manzaneda、Ricardo Meneses、Hakima Es-Samti、Antonio Fernández

  DOI：10.1021/jo900153y

  日期：2009.5.1

  A very expedient and efficient new route toward taiwaniaquinoids, bearing the 4a-methyltetrahydrofluorene skeleton, is reported. Key steps are the intramolecular Friedel−Crafts alkylation of an aryldiene and the degradative oxidation of a methylenedioxy group; the latter process could also be utilized for building the 2-hydroxy-1,4-benzoquinone unit, which is frequently found in natural products. Utilizing

  据报道，一条带有4a-甲基四氢芴骨架的，非常有效和有效的新途径通往台湾喹啉类化合物。关键步骤是芳基二烯的分子内Friedel-Crafts烷基化和亚甲基二氧基的降解氧化。后一种方法也可用于构建天然产物中常见的2-羟基-1,4-苯醌单元。利用这种新方法，已经从商业α-（11a）合成了（±）-二氢呋喃酮（7）（三步，总收率77％）和（±）-taiwaniaquinone H（6）（四步，总收率70％）。）或β-cyclocitral（11b）。
• Design and synthesis of guanidine-containing novel retinoids
  作者：Bhaskar C. Das、Sakkarapalayam M. Mahalingam、Pranoy Mohapatra

  DOI：10.1016/j.tetlet.2009.08.008

  日期：2009.10

  Guanidine-containing new retinoids 1-4 were synthesized through the addition of guanidine to the activated carboxylic acids (retinoids) promoted by carbonyldiimidazole (CDI). A set of structurally and functionally diverse guanidine derivatives of retinoids were obtained in high yields (78-82%). We are in the process of studying the biological effect of these molecules on retinoic acid signaling pathways. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS SE LIANT AUX OPSINES, COMPOSITIONS, ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2011155983A1

  公开（公告）日：2011-12-15

  Compounds are disclosed that are useful for treating ophthalmic conditions related to mislocalization of opsin proteins, the misfolding of mutant opsin proteins and the production of toxic visual cycle products that accumulate in the eye. Compositions of these compounds, either alone or in combination with other therapeutic agents, are also disclosed, along with thereapeutic methods of using such compositions. Methods of synthesizing such compounds are also described.
• [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] LIGANDS LIANT L'OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2012134971A2

  公开（公告）日：2012-10-04

  Compounds and compositions of said compounds along with methods of use of compounds are disclosed for treating ophthalmic conditions related to mislocalization of opsin proteins, the misfolding of mutant opsin proteins and the production of toxic visual cycle products that accumulate in the eye. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described, along with methods of use.