1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-pinacolatoboronaphthalene | 853998-14-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-pinacolatoboronaphthalene
• 英文别名: 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3,2-dioxaborolane
• CAS: 853998-14-8
• 化学式: C₂₀H₃₁BO₂
• 分子量: 314.276
• InChiKey: FUSVGFZGSVYZAI-UHFFFAOYSA-N

物化性质

• 沸点：
  395.2±31.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-pinacolatoboronaphthalene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 sodium carbonate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 tert-butyl 4-(3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOUNDS AS INHIBITORS OF SPHINGOSINE KINASE
  [FR] COMPOSÉS PHARMACEUTIQUES EN TANT QU'INHIBITEURS DE LA SPHINGOSINE KINASE

  摘要：

  本发明涉及一种可用作抑制一种或多种鞘氨醇激酶同工酶活性的化合物。特别是，尽管不仅限于此，本发明还涉及包含这些化合物的药物组合物，以及将这些化合物用于治疗和/或预防癌症、高增殖、炎症、血管生成、免疫和病毒感染性疾病的用途。

  公开号：

  WO2012069852A1
• 作为产物：
  描述：

  2,5-二氯-2,5-二甲基己烷 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三氯化铝 、 potassium acetate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-pinacolatoboronaphthalene
  参考文献：
  名称：

  Stereoselective synthesis of tetrazole CB92834, a potent retinoid compound

  摘要：

  An improved, convergent synthesis of CB92834 is relying on a Suzuki cross-coupling reaction and easily allows multigram-scale preparation of the compound. The approach features three highly stereoselective steps. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.023

文献信息

• Synthesis and applications of 2,4-disubstituted thiazole derivatives as small molecule modulators of cellular development
  作者：Garr-Layy Zhou、Daniel M. Tams、Todd B. Marder、Roy Valentine、Andrew Whiting、Stefan A. Przyborski

  DOI：10.1039/c3ob00005b

  日期：——

  Understanding how the structure of molecules relates to their function and biological activity is essential in the development of new analogues with targeted activity. This is especially relevant in mediating developmental processes in mammalian cells and the regulation of stem cell differentiation. In this study, thiazole-containing small molecules were synthesised and investigated for their ability to induce the differentiation of human pluripotent stem cells and their derivatives. Analyses of cell morphology, cell viability, expression of cell surface markers and ability to induce cell differentiation and regulate neurite formation identified the analogue with the longest and most bulky hydrophobic side chain as possessing comparable or enhanced activity to all-trans-retinoic acid (ATRA). Interestingly, a shorter, less bulky, known thiazole compound reported to be isoform selective for the retinoic acid receptor β2 (RARβ2) agonist did not mediate differentiation under the conditions tested; however, activity could be restored by adjusting the structure to a longer, more bulky molecule. These data provide further insight into the complexity of compound design in terms of developing small molecules with specific biological activities to control the development and differentiation of mammalian cells.

  理解分子结构与其功能和生物活性的关系，对于开发具有特定活性的新类似物至关重要。这在调节哺乳动物细胞的发育过程和干细胞分化中尤为相关。在本研究中，合成了含有噻唑的小分子并研究了它们诱导人多能干细胞及其衍生物分化的能力。通过细胞形态、细胞活力、细胞表面标记物表达以及诱导细胞分化和调节轴突形成能力的分析，发现具有最长和最庞大疏水侧链的类似物活性与全反式维甲酸（ATRA）相当或更强。有趣的是，一种已知的选择性针对维甲酸受体β2（RARβ2）激动剂的较短且较不庞大的噻唑化合物在所测试条件下未诱导分化；然而，通过调整结构为更长、更庞大的分子可以恢复其活性。这些数据为进一步理解在开发具有特定生物活性的小分子以控制哺乳动物细胞发育和分化方面的化合物设计的复杂性提供了深入见解。
• INHIBITORS OF SPHINGOSINE KINASE
  申请人：Stieber Frank

  公开号：US20120252789A1

  公开（公告）日：2012-10-04

  The present invention relates to compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , M 1 , M 2 , M 3 , M 4 , Y 1 , Y 2 , V, W, n, m and o have the meanings given in Claim 1 , and physiologically acceptable salts, derivatives, prodrugs, solvates, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, for use in the treatment of diseases which are influenced by inhibition of Sph kinase 1.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、M1、M2、M3、M4、Y1、Y2、V、W、n、m和o具有权利要求1中给出的含义，以及其生理上可接受的盐、衍生物、前药、溶剂合物、互变异构体和立体异构体，包括所有比例的混合物，用于治疗受Sph激酶1抑制影响的疾病。
• Nickel(0)-Catalyzed Hydroarylation of Styrenes and 1,3-Dienes with Organoboron Compounds
  作者：Li-Jun Xiao、Lei Cheng、Wei-Min Feng、Mao-Lin Li、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1002/anie.201710735

  日期：2018.1.8

  Ni‐catalyzed hydroarylation of styrenes and 1,3‐dienes with organoboron compounds has been developed. The reaction offers a highly selective approach to diarylalkanes and allylarenes under redox‐neutral conditions. In this hydroarylation reaction, a new strategy that uses the proton of methanol to generate the active catalyst species Ni−H was developed. The Ni‐catalyzed hydroarylation, combined with

  已经开发了一种镍催化的苯乙烯和1,3-二烯与有机硼化合物的加氢芳基化反应。该反应在氧化还原中性条件下提供了对二芳基烷烃和烯丙基芳烃的高度选择性方法。在该氢芳基化反应中，开发了一种使用甲醇质子生成活性催化剂物种Ni-H的新策略。Ni催化的氢芳基化结合Ir催化的CH硼酸酯化，可以非常有效且直接地获得视黄酸受体激动剂。
• Inhibitors of sphingosine kinase
  申请人：Stieber Frank

  公开号：US09062015B2

  公开（公告）日：2015-06-23

  The present invention relates to compounds of the formula (I), in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, M1, M2, M3, M4, Y1, Y2, V, W, n, m and o have the meanings given in Claim 1, and physiologically acceptable salts, derivatives, prodrugs, solvates, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, for use in the treatment of diseases which are influenced by inhibition of Sph kinase 1.

  本发明涉及公式（I）的化合物，其中R1，R2，R3，R4，R5，R6，R7，R8，R9，R10，R11，R12，R13，R14，R15，R16，R17，M1，M2，M3，M4，Y1，Y2，V，W，n，m和o具有权利要求书中所给出的含义，并且其生理上可接受的盐，衍生物，前药，溶剂化物，互变异构体和立体异构体，包括所有比例的混合物，用于治疗受Sph激酶1抑制影响的疾病。
• 有机化合物、有机电致发光器件和电子装置
  申请人：陕西莱特光电材料股份有限公司

  公开号：CN115043785B

  公开（公告）日：2023-08-04

  本申请属于有机发光材料领域，具体涉及有机化合物、有机电致发光器件和电子装置。所述有机化合物的结构如式1所示，所述含氮化合物用于有机电致发光器件中，可提高器件的性能。