6-deoxyclitoriracetal | 146163-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-deoxyclitoriracetal
• 英文别名: 6-deoxyclitoriacetal；6-Deoxyclitoracetal；(6aR,12aR)-11,12a-dihydroxy-2,3,9-trimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• CAS: 146163-05-5
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: GAQSUFOBIREXHT-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-deoxyclitoriracetal 在 盐酸 、 sodium hydride 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 11-(3-chloro-2-hydroxy-propoxy)-12a-hydroxy-2,3,9-trimethoxy-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
  参考文献：
  名称：

  Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities

  摘要：

  6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase II alpha inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 mu M. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.052
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 platinum(II) chloride 4-二甲氨基吡啶 、 manganese(IV) oxide 、 AD-mix-α 、 samarium diiodide 、 18-冠醚-6 、 甲基磺酰胺 、 potassium carbonate 、 potassium iodide 、 叔丁醇 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 生成 6-deoxyclitoriracetal
  参考文献：
  名称：

  分离自Collonas Collinsae Craib的6-deoxyclitoriacetal的全合成。

  摘要：

  通过使用铂催化的氢芳基化，Sharpless不对称二羟基化，区域选择性IBX二醇氧化和立体选择性分子内酮-醛频哪醇偶联作为关键步骤，成功地完成了类胡萝卜素6-脱氧clicercercetal的全合成，这是一种细胞毒性天然产物。

  DOI：

  10.1016/j.tetlet.2006.05.188

文献信息

• Co-crystal Structure of 11-Hydroxy-2,3,9-trimethoxy-6H-chromeno[3,4-b]chromen-12-one and 11-Hydroxy-2,3,9-trimethoxy-chromeno[3,4-b]chromene-6,12-dione
  作者：Thapong Teerawatananond、Narongsak Chaichit、Nongnuj Muangsin

  DOI：10.1007/s10870-010-9702-1

  日期：2010.7

  A 1:1 co-crystal structure of 11-hydroxy-2,3,9-trimethoxy-6H-chromeno[3,4-b]chromen-12-one and 11-hydroxy-2,3,9-trimethoxy-chromeno[3,4-b]chromene-6,12-dione (stemonone) was crystallized from the reaction mixture of 6-deoxyclitoriacetal and methanesulfonyl chloride, and its structure was characterized by X-ray diffraction. This co-crystal crystallizes in a triclinic crystal system, space group P(−1) with unit cell parameters of a = 8.1317(3) Å, b = 9.8224(4) Å, c = 10.7268(3) Å, α = 78.116(1)°, β = 77.463(1)°, γ = 77.140(1)°, Z = 2 and V = 804.11(3) Å3. The crystal structure was solved by direct methods and refined by full-matrix least-squares on F 2 to final values of R 1 = 0.0501 and wR 2 = 0.1520. A 1:1 co-crystal structure of 11-hydroxy-2,3,9-trimethoxy-6H-chromeno[3,4-b]chromen-12-one and 11-hydroxy-2,3,9-trimethoxy-chromeno[3,4-b]chromene-6,12-dione (stemonone) is reported.

  1:1共晶结构包括11-羟基-2,3,9-三甲氧基-6H-色满并[3,4-b]色烯-12-酮和11-羟基-2,3,9-三甲氧基-色满并[3,4-b]色烯-6,12-二酮（千金子素），从6-去氧阴蒂叉醚和甲磺酰氯的反应混合物中结晶出来，并通过X射线衍射进行了结构表征。该共晶属于三斜晶系，空间群为P(-1)，晶胞参数为a = 8.1317(3) Å，b = 9.8224(4) Å，c = 10.7268(3) Å，α = 78.116(1)°，β = 77.463(1)°，γ = 77.140(1)°，Z = 2，V = 804.11(3) Å3。晶体结构通过直接法求解，并通过F2上的全矩阵最小二乘法精修至最终的R1 = 0.0501和wR2 = 0.1520。报告了一种11-羟基-2,3,9-三甲氧基-6H-色满并[3,4-b]色烯-12-酮和11-羟基-2,3,9-三甲氧基-色满并[3,4-b]色烯-6,12-二酮（千金子素）的1:1共晶结构。
• Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities
  作者：Supranee Sangthong、Kuakarun Krusong、Nattaya Ngamrojanavanich、Tirayut Vilaivan、Songchan Puthong、Supajittra Chandchawan、Nongnuj Muangsin

  DOI：10.1016/j.bmcl.2011.06.052

  日期：2011.8

  6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase II alpha inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC50 values ranging from 0.38 to 0.73 mu M. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property. (C) 2011 Elsevier Ltd. All rights reserved.
• Total synthesis of 6-deoxyclitoriacetal isolated from Stemona collinsae Craib.
  作者：Prapas Khorphueng、Jumreang Tummatorn、Amorn Petsom、Richard J.K. Taylor、Sophon Roengsumran

  DOI：10.1016/j.tetlet.2006.05.188

  日期：2006.8

  A total synthesis of the rotenoid, 6-deoxyclitoriacetal, a cytotoxic natural product, was successfully achieved by using platinum-catalysed hydroarylation, Sharpless asymmetric dihydroxylation, regioselective IBX diol oxidation and stereoselective intramolecular keto-aldehyde pinacol coupling as the key steps.

  通过使用铂催化的氢芳基化，Sharpless不对称二羟基化，区域选择性IBX二醇氧化和立体选择性分子内酮-醛频哪醇偶联作为关键步骤，成功地完成了类胡萝卜素6-脱氧clicercercetal的全合成，这是一种细胞毒性天然产物。