2-Hexyl-2,3-dihydrobenzopyran | 149548-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-Hexyl-2,3-dihydrobenzopyran
• 英文别名: 2-hexyl-3,4-dihydro-2H-chromene
• CAS: 149548-66-3
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: MNGNHLIWLMWVDB-UHFFFAOYSA-N

物化性质

• 沸点：
  312.3±12.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Hexyl-2,3-dihydrobenzopyran 在 溴 作用下， 以 乙醇 为溶剂， 以89%的产率得到6-Bromo-2-hexyl-2,3-dihydrobenzopyran
  参考文献：
  名称：

  Synthesis and Properties of a New Family of Chiral Mesogens Containing the 2,3-Dihydrobenzopyran Nucleus

  摘要：

  A new class of mesogens A with a central chiral core based on the 2,3-dihydrobenzopyran nucleus was synthesized both in the racemic and optically pure form, and the thermotropic properties were studied. The distortion from structural linearity due to the presence of the 2,3-dihydropyran ring does not inhibit the existence of mesophases, and Ch, S-A, and S-C phases were observed according to the substituents present. The conformational constrictions imposed by cyclization proved not to be very important in determining the compactness of the cholesteric helix.

  DOI：

  10.1021/jo00099a022
• 作为产物：
  描述：

  庚酸乙酯 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 反应 60.0h， 生成 2-Hexyl-2,3-dihydrobenzopyran
  参考文献：
  名称：

  Synthesis and Properties of a New Family of Chiral Mesogens Containing the 2,3-Dihydrobenzopyran Nucleus

  摘要：

  A new class of mesogens A with a central chiral core based on the 2,3-dihydrobenzopyran nucleus was synthesized both in the racemic and optically pure form, and the thermotropic properties were studied. The distortion from structural linearity due to the presence of the 2,3-dihydropyran ring does not inhibit the existence of mesophases, and Ch, S-A, and S-C phases were observed according to the substituents present. The conformational constrictions imposed by cyclization proved not to be very important in determining the compactness of the cholesteric helix.

  DOI：

  10.1021/jo00099a022

文献信息

• Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis
  作者：Hairong Lyu、Ilia Kevlishvili、Xuan Yu、Peng Liu、Guangbin Dong

  DOI：10.1126/science.abg5526

  日期：2021.4.9

  (C−O) bond in alkyl ethers could simplify chemical syntheses through the elaboration of these robust, readily available precursors. Here we report that dibromoboranes react with alkyl ethers in the presence of a nickel catalyst and zinc reductant to insert boron into the C−O bond. Subsequent reactivity can effect oxygen-to-nitrogen substitution or one-carbon homologation of cyclic ethers and more broadly

  轻度的在烷基醚中裂解碳-氧（C-O）键的方法可通过精心设计这些稳固且易于获得的前体来简化化学合成。在这里，我们报道二溴硼烷在镍催化剂和锌还原剂的存在下与烷基醚反应，从而将硼插入到C-O键中。随后的反应性可以影响环醚的氧-氮取代或一碳同系化，并更广泛地简化了生物活性化合物的制备。机理研究揭示了通过锌/镍串联催化的裂解-然后反弹的途径。
• Design, synthesis and docking-based 3D-QSAR study of novel 2-substituted 2-aminopropane-1,3-diols as potent and selective agonists of sphingosine-1-phosphate 1 (S1P1) receptor
  作者：Yulin Tian、Jing Jin、Xiaojian Wang、Weijuan Han、Gang Li、Wanqi Zhou、Qiong Xiao、Jianguo Qi、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c3md00079f

  日期：——

  Spingosine-1-phosphate receptor 1 (S1P1) has been actively pursued as an important therapeutic target in immune regulation. A series of 2-substituted 2-aminopropane-1,3-diols were designed and synthesized as selective S1P1 agonists. Most of the compounds with a biphenyl ether scaffold showed moderate to excellent S1P1/S1P3 selectivity. Compound 40c is identified as a potent S1P1 agonist with 350-fold S1P1/S1P3

  Spingosine-1-磷酸受体1（S1P 1）已被积极追求为免疫调节中的重要治疗靶标。设计并合成了一系列2-取代的2-氨基丙烷-1,3-二醇作为选择性的S1P 1激动剂。大多数具有联苯醚支架的化合物显示出中等至出色的S1P 1 / S1P 3选择性。化合物40c被鉴定为具有350倍S1P 1 / S1P 3选择性的有效S1P 1激动剂。39c，40c的酒精形式在体内具有良好的淋巴细胞减少活性但对心率的影响微弱。为了更详细地研究2-取代的2-氨基丙烷-1,3-二醇的比吸收比，建立了COMFA（q 2 = 0.547 ，r 2 = 0.986）和COMSIA（q 2 = 0.544，r 2 = 0.943）模型。关于分子对接比对的研究，在预测激动剂的活性方面具有很高的可靠性。3D-QSAR模型将有助于设计新颖，有效和选择性的S1P 1激动剂。
• [EN] HYDROXY PROPANEDIOL DERIVATIVES, THEIR PREPARATIVE METHOD, PHARMACEUTICAL COMPOSITIONS AND USE<br/>[FR] DÉRIVÉS D'HYDROXYPROPANEDIOL, LEUR PROCÉDÉ DE PRÉPARATION, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET LEUR UTILISATION
  申请人：INST MATERIA MEDICA CAMS

  公开号：WO2011147311A1

  公开（公告）日：2011-12-01

  Compounds represented by formula (I), preparative method thereof and pharmaceutical compositions containing them and use thereof as immuno-regulation agents. The compounds can treat immunologic derangement, immunosuppression, hypoimmunity, rejection after organ transplantation, and autoimmune disease.
• Synthesis and Properties of a New Family of Chiral Mesogens Containing the 2,3-Dihydrobenzopyran Nucleus
  作者：Bianca F. Bonini、Paolo Carboni、Giovanni Gottarelli、Stefano Masiero、Gian Piero Spada

  DOI：10.1021/jo00099a022

  日期：1994.10

  A new class of mesogens A with a central chiral core based on the 2,3-dihydrobenzopyran nucleus was synthesized both in the racemic and optically pure form, and the thermotropic properties were studied. The distortion from structural linearity due to the presence of the 2,3-dihydropyran ring does not inhibit the existence of mesophases, and Ch, S-A, and S-C phases were observed according to the substituents present. The conformational constrictions imposed by cyclization proved not to be very important in determining the compactness of the cholesteric helix.