5-bromo-2,2-dimethyl-2H-chroman-6-ol | 360578-26-3

• 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: 5-bromo-2,2-dimethyl-2H-chroman-6-ol
• 英文别名: 5-Bromo-2,2-dimethyl-3,4-dihydrochromen-6-ol；5-bromo-2,2-dimethyl-3,4-dihydrochromen-6-ol
• CAS: 360578-26-3
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: SRRJVJSAHBMDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-碘吡啶 、 5-bromo-2,2-dimethyl-2H-chroman-6-ol 在 碳酸氢钠 作用下， 反应 2.0h， 以43%的产率得到4-(5-bromo-2,2-dimethyl-2H-chroman-6-yloxy)pyridine
  参考文献：
  名称：

  Antimycobacterial Benzofuro[3,2-f]chromenes from a 5-Bromochromen-6-ol

  摘要：

  在合成特定的抗分枝杆菌药物3,3-二甲基-3H-苯并呋喃并[3,2-f]苯并吡喃的类似物时，我们制备了以前未报道的5-溴-2,2-二甲基-2H-苯并吡喃-6-醇。我们想在此报告使用该化合物的原始合成方案。首先研究了各种5-溴-2,2-二甲基-6-(芳基氧基)-2H-苯并吡喃的制备。随后进行了钯催化的环化反应，该反应仅在有空气存在的情况下发生，并导致3,3-二甲基-3H-苯并呋喃并[3,2-f]苯并吡喃或3,3-二甲基-3H-4,7-二氧杂-10-氮杂苯并[c]芴。这些类似物的抗分枝杆菌特性已经过研究。

  DOI：

  10.1055/s-2007-966019
• 作为产物：
  描述：

  methyl 3-(3-bromo-4-hydroxyphenyl)propanoate 在 三氟化硼乙醚 、 lithium perchlorate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 5-bromo-2,2-dimethyl-2H-chroman-6-ol
  参考文献：
  名称：

  Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans

  摘要：

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00479-3

文献信息

• Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans
  作者：Kazuki Mori、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4020(01)00479-3

  日期：2001.6

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Antimycobacterial Benzofuro[3,2-<i>f</i>]chromenes from a 5-Bromochromen-6-ol
  作者：Yves Janin、Soizic Prado、Valérie Toum、Brigitte Saint-Joanis、Sylvie Michel、Michel Koch、Stewart Cole、François Tillequin

  DOI：10.1055/s-2007-966019

  日期：——

  In the course of our work on the synthesis of analogues of the specific antimycobacterial 3,3-dimethyl-3H-benzofuro[3,2-f]chromene, we prepared the previously unreported 5-bromo-2,2-dimethyl-2H-chromen-6-ol. We wish to report here an original synthetic scheme using this compound. The preparation of various 5-bromo-2,2-dimethyl-6-(aryloxy)-2H-chromenes was first investigated. This was followed by a palladium-catalysed cyclisation reaction, which takes place only in the presence of air, and leads to 3,3-dimethyl-3H-benzofuro[3,2-f]chromenes or 3,3-dimethyl-3H-4,7-dioxa-10-aza-benzo[c]fluorene. The antimycobacterial properties of these analogues have been investigated.

  在合成特定的抗分枝杆菌药物3,3-二甲基-3H-苯并呋喃并[3,2-f]苯并吡喃的类似物时，我们制备了以前未报道的5-溴-2,2-二甲基-2H-苯并吡喃-6-醇。我们想在此报告使用该化合物的原始合成方案。首先研究了各种5-溴-2,2-二甲基-6-(芳基氧基)-2H-苯并吡喃的制备。随后进行了钯催化的环化反应，该反应仅在有空气存在的情况下发生，并导致3,3-二甲基-3H-苯并呋喃并[3,2-f]苯并吡喃或3,3-二甲基-3H-4,7-二氧杂-10-氮杂苯并[c]芴。这些类似物的抗分枝杆菌特性已经过研究。