5,6-dihydro-benzo[c]xanthen-7-one | 28658-20-0

• 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: 5,6-dihydro-benzo[c]xanthen-7-one
• 英文别名: 5,6-Dihydrobenzo[c]xanthen-7-one
• CAS: 28658-20-0
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: MWEIPTNKVKWWKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 四氢吡咯 、 盐酸 、 hydroxy(tosyloxy)iodobenzene 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 5,6-dihydro-benzo[c]xanthen-7-one
  参考文献：
  名称：

  螺环化的chroman-4-ones的氧化环扩展：类胡萝卜素核心和相关的苯并氧杂蒽的合成

  摘要：

  Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10646-3

文献信息

• Tetrahydroxanthones by Sequential Pd-Catalyzed C−O and C−C Bond Construction and Use in the Identification of the “Antiausterity” Pharmacophore of the Kigamicins
  作者：Penelope A. Turner、Ellanna M. Griffin、Jacqueline L. Whatmore、Michael Shipman

  DOI：10.1021/ol103103n

  日期：2011.3.4

  Readily available C-acylated cycloalkanones undergo efficient Pd catalyzed ring closure/cross-coupling providing 7-substituted tetrahydroxanthones in a single operation. One of the synthesized derivatives (depicted) is shown to selectively kill pancreatic cancer (PANC-1) cells under conditions of nutrient deprivation indicating that the tetrahydroxanthone is responsible, in part, for the “antiausterity”

  易于获得的C-酰化环烷酮经过有效的Pd催化的闭环/交叉偶联，可在一次操作中提供7个取代的四氢氧杂蒽。已显示一种合成的衍生物（已描述）在营养剥夺的条件下选择性杀死胰腺癌（PANC-1）细胞，这表明四氢黄酮在某种程度上负责天然存在的基加米星的“抗紧缩”作用。
• The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones
  作者：Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron、Jean-Luc Thomas

  DOI：10.1016/s0040-4039(97)10646-3

  日期：1998.2

  Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones. (C) 1998 Elsevier Science Ltd. All rights reserved.