6-Ethenyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene | 119999-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-Ethenyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene
• 英文别名: 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-vinylnaphthalene；1,1,4,4-tetramethyl-6-vinyl-1,2,3,4-tetrahydronaphthalene；6-Ethenyl-1,1,4,4-tetramethyl-2,3-dihydronaphthalene
• CAS: 119999-19-8
• 化学式: C₁₆H₂₂
• 分子量: 214.351
• InChiKey: KPJCDZOHUQRWSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-Ethenyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 1.5h， 以88%的产率得到1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethane-1,2-diol
  参考文献：
  名称：

  苯并二氧六环类衍生物、其制备方法及其在医 药上的应用

  摘要：

  本发明涉及苯并二氧六环类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的新的苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物、及其制备方法，本发明进一步涉及所述苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物在制备治疗剂，特别是GPR40激动剂，和在制备治疗糖尿病和代谢性病症等疾病的药物中的用途，其中通式(I)的各取代基同说明书中的定义相同。

  公开号：

  CN103030646B
• 作为产物：
  描述：

  2,5-二甲基-2,5-己二醇 在 盐酸 、 aluminum (III) chloride 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 25.67h， 生成 6-Ethenyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene
  参考文献：
  名称：

  苯并二氧六环类衍生物、其制备方法及其在医 药上的应用

  摘要：

  本发明涉及苯并二氧六环类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的新的苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物、及其制备方法，本发明进一步涉及所述苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物在制备治疗剂，特别是GPR40激动剂，和在制备治疗糖尿病和代谢性病症等疾病的药物中的用途，其中通式(I)的各取代基同说明书中的定义相同。

  公开号：

  CN103030646B

文献信息

• Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres
  作者：Wanlan Su、Jide Zhu、Yu Chen、Xu Zhang、Weihua Qiu、Kai Yang、Peiyuan Yu、Qiuling Song

  DOI：10.1038/s41557-024-01505-0

  日期：——

  replacement has emerged as a clear strategy for drug-structure optimization. Naphthalene is the core element of many chiral pharmaceuticals and drug candidates. However, as a promising isostere of naphthalene, the chiral version of 1,2-benzazaborine has rarely been explored due to the lack of efficient synthetic methods. Here we describe a copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines

  生物等排替代已成为药物结构优化的明确策略。萘是许多手性药物和候选药物的核心元素。然而，作为一种有前途的萘电子等排体，由于缺乏有效的合成方法，1,2-苯并硼啉的手性版本很少被探索。在这里，我们描述了铜催化的烯烃与 1,2-苯并氮硼烷的对映选择性硼氢化反应。该方法为原子经济且高效地构建具有 2-碳立体中心或丙二烯骨架的多种手性 1,2-苯并氮杂硼化合物（超过 60 个实例）提供了一个通用平台，具有高产率和优异的对映选择性。已经制备了三种具有生物活性的手性含萘分子的1,2-苯并硼烷类似物，并且还开发了一系列围绕手性1,2-苯并氮硼烷的转化。值得注意的是，本研究的硼氢化过程表明，1,2-苯并氮杂硼啉的特性在限速步骤和催化剂静止状态中起着至关重要的作用。
• Heterocycle-Containing Retinoids. Discovery of a Novel Isoxazole Arotinoid Possessing Potent Apoptotic Activity in Multidrug and Drug-Induced Apoptosis-Resistant Cells
  作者：Daniele Simoni、Marinella Roberti、Francesco Paolo Invidiata、Riccardo Rondanin、Riccardo Baruchello、Cinzia Malagutti、Angelica Mazzali、Marcello Rossi、Stefania Grimaudo、Francesca Capone、Luisa Dusonchet、Maria Meli、Maria Valeria Raimondi、Marilena Landino、Natale D'Alessandro、Manlio Tolomeo、Dhar Arindam、Shennan Lu、Doris M. Benbrook

  DOI：10.1021/jm0010320

  日期：2001.7.1

  In a search for retinoic acid (RA) receptor ligands endowed with potent apoptotic activity, a series of novel arotinoids were prepared. Because the stereochemistry of the CS-alkenyl portion of natural 9-cis-RA and the olefinic moiety of the previously synthesized isoxazole retinoid 4 seems to have particular importance for their apoptotic activity, novel retinoid analogues with a restricted or, vice versa, a larger flexibility in this region were designed and prepared. The new compounds were evaluated in vitro for their ability to activate natural retinoid receptors and for their differentiation-inducing activity. Cytotoxic and apoptotic activities were, in addition, evaluated. In general, these analogues showed low cytotoxicity, with the restricted structures being slightly more active than the more flexible ones. As an exception, however, the isoxazole retinoid 15b proved to be particularly able to induce apoptosis at concentrations <5 muM, showing a higher activity than the classical retinoids such as all-trans-RA, 13-cis-RA, and 9-cis-RA and the previously described synthetic retinoid 4. 15b also exhibited a good affinity for the retinoid receptors. Interestingly, another important property of 15b was its ability to induce apoptosis in the HL60R multidrug-resistant (MDR) cell line, at the same concentration as is effective in HL60. Therefore, 15b represents a new retinoid possessing high apoptotic activity in an MDR cell line. The ability of 15b to act on K562 and HL60R cells suggests that this compound may have important implications in the treatment of different leukemias, and its structure could offer an interesting model for the design of new compounds endowed with apoptotic activity on MDR- and retinoid-resistant malignancies.
• Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids
  作者：Marcia I. Dawson、Peter D. Hobbs、Krzysztof A. Derdzinski、Wan Ru Chao、Gernot Frenking、Gilda H. Loew、Anton M. Jetten、Joseph L. Napoli、John B. Williams

  DOI：10.1021/jm00127a018

  日期：1989.7

  A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propenyl ] benzoic acid--(E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2 - propenyl]benzoic acid, (E)-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-bu ten- 2-yl]benzoic acid, trans-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) cyclopropyl]benzoic acid, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid, 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid, 6-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid and 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-5-methyl-2- naphthalenecarboxylic acid--were synthesized and screened for retinoid biological activity. Comparison of the conformers of these analogues generated by molecular mechanics calculations with the biological activity profiles of these compounds indicates that geometric constraints required for high biological activity are imposed on the bridge joining the two aromatic ring systems by the retinoid receptor.
• DAWSON, MARCIA I.;HOBBS, PETER D.;DERDZINSKI, KRZYSZTOF A.;CHAO, WAN-RU;F+, J. MED. CHEM., 32,(1989) N, C. 1504-1517
  作者：DAWSON, MARCIA I.、HOBBS, PETER D.、DERDZINSKI, KRZYSZTOF A.、CHAO, WAN-RU、F+

  DOI：——

  日期：——
• 苯并二氧六环类衍生物、其制备方法及其在医 药上的应用
  申请人：上海恒瑞医药有限公司

  公开号：CN103030646B

  公开（公告）日：2016-08-24

  本发明涉及苯并二氧六环类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的新的苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物、及其制备方法，本发明进一步涉及所述苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物在制备治疗剂，特别是GPR40激动剂，和在制备治疗糖尿病和代谢性病症等疾病的药物中的用途，其中通式(I)的各取代基同说明书中的定义相同。