4a-hydroxy-8-methoxy-3,4-dihydro-2H-xanthen-1-one | 1320360-02-8

• 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: 4a-hydroxy-8-methoxy-3,4-dihydro-2H-xanthen-1-one
• CAS: 1320360-02-8
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: WFZKMQNJCVNGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4a-hydroxy-8-methoxy-3,4-dihydro-2H-xanthen-1-one 在 溶剂黄146 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 16.0h， 生成 2,3,4,9-tetrahydro-9-ethyl-8-methoxy-1H-xanthen-1-one
  参考文献：
  名称：

  Multicomponent Coupling Reaction Using Arynes: Synthesis of Xanthene Derivatives

  摘要：

  One-pot synthesis of xanthene derivatives was achieved by a route involving the cascade three-component coupling reaction of arynes with DMF and active methylenes followed by the S(N)2' reaction of three-component coupling products with thiols. The reactivity of three-component coupling products toward nucleophiles and the further conversion of oxygen heterocycles allowing facile incorporation of structural variety were studied.

  DOI：

  10.1021/acs.joc.5b01452
• 作为产物：
  描述：

  1,3-环己二酮 、 N,N-二甲基甲酰胺 、 三氟甲烷磺酸3-甲氧基-2-(三甲基硅基)苯酯 在 四丁基氟化铵 作用下， 反应 12.0h， 以83%的产率得到4a-hydroxy-8-methoxy-3,4-dihydro-2H-xanthen-1-one
  参考文献：
  名称：

  芳烃插入甲酰胺的CO键引起的多组分偶联反应

  摘要：

  芳烃可以做到三点：芳烃，DMF和活性亚甲基的三组分偶联为2 H-色烯和香豆素衍生物的合成提供了一种有效的方法（参见方案）。顺序多步反应是由芳烃和中间体中应变能的释放驱动的，这一发现得到了热力学的支持。

  DOI：

  10.1002/anie.201102088

文献信息

• Aqueous-Medium Selective Modification of Cysteine and Related Thiols with Tricyclic Oxygen-Heterocycles
  作者：Hideto Miyabe、Eito Yoshioka、Yuya Goto、Ikko Minato

  DOI：10.1055/s-0036-1588497

  日期：2017.11

  The utility of tricyclic oxygen-heterocycles as a reagent for the thiol-selective modification toward bioconjugation was demonstrated by the use of l-cysteine, homocysteine, captopril, and glutathione as a nucleophile having a thiol group. These trapping reactions proceeded under the mild and aqueous reaction conditions.

  三环氧杂环化合物作为对巯基选择性修饰的试剂在生物共轭中的实用性通过使用半胱氨酸、同型半胱永、卡普托普利和谷胱甘肽作为含有巯基的亲核试剂得到了证明。这些捕获反应在温和和水性反应条件下进行。
• Multicomponent Coupling Reaction Using Arynes: Synthesis of Xanthene Derivatives
  作者：Eito Yoshioka、Masatoshi Nishimura、Takashi Nakazawa、Shigeru Kohtani、Hideto Miyabe

  DOI：10.1021/acs.joc.5b01452

  日期：2015.8.21

  One-pot synthesis of xanthene derivatives was achieved by a route involving the cascade three-component coupling reaction of arynes with DMF and active methylenes followed by the S(N)2' reaction of three-component coupling products with thiols. The reactivity of three-component coupling products toward nucleophiles and the further conversion of oxygen heterocycles allowing facile incorporation of structural variety were studied.
• A Multicomponent Coupling Reaction Induced by Insertion of Arynes into the CO Bond of Formamide
  作者：Eito Yoshioka、Shigeru Kohtani、Hideto Miyabe

  DOI：10.1002/anie.201102088

  日期：2011.7.11

  And aryne makes three: The three‐component coupling of arynes, DMF, and active methylenes has provided an efficient method for the synthesis of 2H‐chromene and coumarin derivatives (see scheme). The sequential multistep reactions are driven by the release of strain energy in the arynes and intermediates, and this finding was supported by thermodynamics.

  芳烃可以做到三点：芳烃，DMF和活性亚甲基的三组分偶联为2 H-色烯和香豆素衍生物的合成提供了一种有效的方法（参见方案）。顺序多步反应是由芳烃和中间体中应变能的释放驱动的，这一发现得到了热力学的支持。