1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl benzoate | 1392502-49-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl benzoate
• 英文别名: (1,6,6-trimethyl-10,11-dioxo-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-9-yl) benzoate
• CAS: 1392502-49-6
• 化学式: C₂₆H₂₂O₅
• 分子量: 414.458
• InChiKey: GXRHJEGKGAGDJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl benzoate 在 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以63%的产率得到7,7-difluoro-6,6-dihydroxy-1,1-dimethyl-5,8-dioxo-1,2,3,4,5,6,7,8-octahydrophenanthren-4-yl benzoate
  参考文献：
  名称：

  呋喃萘醌的二氟化

  摘要：

  基于天然产物丹参酮及其类似物的呋喃萘醌骨架，开发了前所未有的二氟化反应。通过使用Selectfluor作为氟化源和H 2 O作为羟基源，获得了多种独特的多环α，α-二氟β，β-二羟基对苯醌产物，收率高达90％。机理研究表明，该反应可能会经历多个亲电和亲核取代，以及C–O和C–C键的断裂。该方法不仅为合成α，α-二氟酮提供了一种新方法，而且为生物学活性筛选提供了一系列独特的化学型。

  DOI：

  10.1021/acs.joc.7b01064
• 作为产物：
  描述：

  丹参酮 IIA 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl benzoate
  参考文献：
  名称：

  Design, synthesis and vasodilative activity of tanshinone IIA derivatives

  摘要：

  A new series of tanshinone IIA (DIIA) derivatives were synthesized through the reaction of brominated tanshinone IIA (1-Br DIIA) and aromatic acids in the presence of K2CO3. Twenty compounds were synthesized, and all of them were novel. Vasodilative activities for synthesized compounds were valuated in vitro on the contractile response of vascular thoracic aorta smooth muscle from Wistar rats. The results showed that most compounds exhibited a concentration-dependent inhibition on the contractile response of norepinephrine. Four prepared compounds, 4, 5, 8 and 13 revealed relatively remarkable vasodilative activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.014

文献信息

• 二氟二羟基萘二酮类化合物、制备方法和应用
  申请人：中国科学院上海药物研究所

  公开号：CN109020799B

  公开（公告）日：2021-08-10

  本发明涉及一类2,2‑二氟‑3,3‑二羟基‑2,3‑二氢化萘‑1,4‑二酮类化合物、其制备方法和应用。其制备方法条件温和、简便易操作，适用于大量合成。其可以用于制抗肿瘤药物。
• Catalyst-Free sp³ C–H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA
  作者：Chunyong Ding、Jie Li、Mingkun Jiao、Ao Zhang

  DOI：10.1021/acs.jnatprod.6b00370

  日期：2016.10.28

  Tanshinone IIA is a valuable bioactive natural product isolated from the well-known Chinese herb Danshen. Structural manipulation of the A-ring of tanshinone IIA is rather limited. In this study, a substrate tautomerization-induced catalyst-free benzylic sp(3) C-H acyloxylation approach is reported that allows the direct introduction of various acyloxy groups at the A-ring benzylic methylene of various tanshinone IIA substrates, thus avoiding the use of expensive transition metal catalysts and the production of harmful byproducts. This approach features a unique acid-induced reversible enolization/oxa-conjugate addition process followed by oxidation to exclusively give a series of diverse 1-acyloxylated derivatives under simple conditions in a regioselective manner. Compared with the literature procedures, this protocol demonstrates a higher efficiency, a more robust functional-group tolerance, atom economy, and lower cost.
• Design, synthesis and vasodilative activity of tanshinone IIA derivatives
  作者：Yue-Feng Bi、Zhen-Ji Wang、Ruo-Fei Guan、Yu-Ting Ye、Yuan-Yuan Chen、Yan-Bing Zhang、Hong-Min Liu

  DOI：10.1016/j.bmcl.2012.05.014

  日期：2012.8

  A new series of tanshinone IIA (DIIA) derivatives were synthesized through the reaction of brominated tanshinone IIA (1-Br DIIA) and aromatic acids in the presence of K2CO3. Twenty compounds were synthesized, and all of them were novel. Vasodilative activities for synthesized compounds were valuated in vitro on the contractile response of vascular thoracic aorta smooth muscle from Wistar rats. The results showed that most compounds exhibited a concentration-dependent inhibition on the contractile response of norepinephrine. Four prepared compounds, 4, 5, 8 and 13 revealed relatively remarkable vasodilative activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Difluorination of Furonaphthoquinones
  作者：Jie Li、Yu Xue、Zhoulong Fan、Chunyong Ding、Ao Zhang

  DOI：10.1021/acs.joc.7b01064

  日期：2017.7.21

  a wide range of unique polycyclic α,α-difluoro β,β-dihydroxyl para-quinone products were achieved with yields up to 90%. The mechanistic studies revealed that the reaction might undergo tandem multiple electrophilic and nucleophilic substitutions, as well as cleavages of C–O and C–C bonds. This approach not only provides a new method to synthesis of α,α-difluoro ketones, but also affords a series

  基于天然产物丹参酮及其类似物的呋喃萘醌骨架，开发了前所未有的二氟化反应。通过使用Selectfluor作为氟化源和H 2 O作为羟基源，获得了多种独特的多环α，α-二氟β，β-二羟基对苯醌产物，收率高达90％。机理研究表明，该反应可能会经历多个亲电和亲核取代，以及C–O和C–C键的断裂。该方法不仅为合成α，α-二氟酮提供了一种新方法，而且为生物学活性筛选提供了一系列独特的化学型。