2-[2-(2-hydroxyphenyl)ethyl]chromone | 1089338-38-4

• 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-[2-(2-hydroxyphenyl)ethyl]chromone
• 英文别名: 2-[2-(2-Hydroxyphenyl)ethyl]chromen-4-one
• CAS: 1089338-38-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: LGWJJSZGQWTDID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2-hydroxyphenyl)ethyl]chromone 在 potassium carbonate 作用下， 反应 0.5h， 以62%的产率得到2,2'-spirobi[chroman]-4-one
  参考文献：
  名称：

  Synthesis of 6,6-bisbenzannulated spiroketals related to the rubromycins using a double intramolecular hetero-Michael addition (DIHMA)

  摘要：

  The synthesis of a series of 6,6-bisbenzannulated spiroketals using a novel microwave-assisted DIHMA approach is reported. Coupling of ail aryl acetylene and an aryl aldehyde via acetylide anion addition resulted in the formation of an alkynol which was followed by oxidation to the desired ynone. Spirocyclization using the DIHMA Protocol afforded the desired bisbenzannulated spiroketal in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.030
• 作为产物：
  描述：

  2-[2-[2-(Ethoxymethoxy)phenyl]ethyl]chromen-4-one 在 四溴化碳 作用下， 以 异丙醇 为溶剂， 以97%的产率得到2-[2-(2-hydroxyphenyl)ethyl]chromone
  参考文献：
  名称：

  Synthesis of 6,6-bisbenzannulated spiroketals related to the rubromycins using a double intramolecular hetero-Michael addition (DIHMA)

  摘要：

  The synthesis of a series of 6,6-bisbenzannulated spiroketals using a novel microwave-assisted DIHMA approach is reported. Coupling of ail aryl acetylene and an aryl aldehyde via acetylide anion addition resulted in the formation of an alkynol which was followed by oxidation to the desired ynone. Spirocyclization using the DIHMA Protocol afforded the desired bisbenzannulated spiroketal in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.030

文献信息

• Synthesis of Benzannulated [6,6]-Spiroketals by a One-Pot Carbonylative Sonogashira Coupling/Double Annulation Reaction
  作者：Kuirong Xiang、Pei Tong、Baorun Yan、Lingling Long、Chunbo Zhao、Yuan Zhang、Ying Li

  DOI：10.1021/acs.orglett.8b03586

  日期：2019.1.18

  A one-pot Pd-catalyzed carbonylative Sonogashira coupling in tandem with double annulation reaction to synthesize benzannulated [6,6]-spiroketals from o-iodophenols and terminal alkynols or alkynyl phenols was achieved. The protocol provides straightforward and facile access to benzannulated [6,6]-spiroketals in moderate to good yields and excellent diastereoselectivities under balloon pressure of

  实现了单锅钯催化的羰基化Sonogashira偶联与双环反应，从邻碘苯酚和末端炔醇或炔基酚合成苯并[6,6]-螺缩酮。该协议提供了在中度到良好的产率和在室温下在CO的球囊压力下出色的非对映选择性的简便易行的途径，可接近苯环化的[6,6]-螺酮。
• Synthesis of 6,6-bisbenzannulated spiroketals related to the rubromycins using a double intramolecular hetero-Michael addition (DIHMA)
  作者：Peter J. Choi、Dominea C.K. Rathwell、Margaret A. Brimble

  DOI：10.1016/j.tetlet.2009.02.030

  日期：2009.7

  The synthesis of a series of 6,6-bisbenzannulated spiroketals using a novel microwave-assisted DIHMA approach is reported. Coupling of ail aryl acetylene and an aryl aldehyde via acetylide anion addition resulted in the formation of an alkynol which was followed by oxidation to the desired ynone. Spirocyclization using the DIHMA Protocol afforded the desired bisbenzannulated spiroketal in good yield. (C) 2009 Elsevier Ltd. All rights reserved.