p-diacetylbenzene bis-enol trimethylsilyl ether | 183060-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-diacetylbenzene bis-enol trimethylsilyl ether
• 英文别名: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether；Trimethyl-[1-[4-(1-trimethylsilyloxyethenyl)phenyl]ethenoxy]silane
• CAS: 183060-22-2
• 化学式: C₁₆H₂₆O₂Si₂
• 分子量: 306.552
• InChiKey: CEHCQTSDIADTDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  蒿甲醚 、 p-diacetylbenzene bis-enol trimethylsilyl ether 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以26%的产率得到10-p-acetylphenylartemisinin dimer
  参考文献：
  名称：

  Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers

  摘要：

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.

  DOI：

  10.1021/jm990363d
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 1,4-二乙酰苯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以59%的产率得到p-diacetylbenzene bis-enol trimethylsilyl ether
  参考文献：
  名称：

  Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers

  摘要：

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.

  DOI：

  10.1021/jm990363d

文献信息

• Copper(II) Triflate-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes. A Straightforward Synthetic Route to Polysubstituted Furans
  作者：Zhuang-ping Zhan、Shao-pei Wang、Xu-bin Cai、Hui-juan Liu、Jing-liang Yu、Yuan-yuan Cui

  DOI：10.1002/adsc.200700234

  日期：2007.9.3

  A novel and efficient procedure for the synthesis of γ-alkynyl ketones by the nucleophilic substitution of propargylic acetates with enoxysilanes in the presence of a catalytic amount of Copper(II) triflate, has been developed. The substitution reaction can be followed by a 4-toluenesulfonic acid-catalyzed cyclization without purification of the γ-alkynyl ketone intermediates, offering a straightforward

  已经开发了在催化量的三氟甲磺酸铜（II）存在下通过用环氧硅烷的炔丙基乙酸酯的亲核取代合成γ-炔基酮的新颖而有效的方法。取代反应之后可以进行4-甲苯磺酸催化的环化反应，而无需纯化γ-炔基酮中间体，从而提供了直接的合成路线来制备多取代的呋喃。
• Synthesis and structure of polyunsaturated [10]paracyclophane annulated by two azulene rings
  作者：Shigeyasu Kuroda、Yuji Obata、Nguyen Chung Thanh、Ryuta Miyatake、Yoshikazu Horino、Mitsunori Oda

  DOI：10.1016/j.tetlet.2007.11.067

  日期：2008.1

  The polyunsaturated [10]cyclophane 4 was synthesized from 1,4-diacetylbenzene by a four-step sequence involving the modified Yasunami azulene synthesis, introduction of two butenone units, and a subsequent McMurry coupling reaction. The crystal structures of 4 and the synthetic intermediate 8 was determined by X-ray crystallographic analysis and the results reveal that (1) the benzene ring of 4 is

  多价不饱和的[10]环烷4是由1,4-二乙酰基苯按四步顺序合成的，该步骤涉及修饰的Yasunami z合成，引入两个丁烯酮单元以及随后的McMurry偶联反应。通过X射线晶体学分析确定4和合成中间体8的晶体结构，结果表明（1）4的苯环扭曲为具有相对较小弯曲角度的船形，（2）苯并的a环图8显示了沿着短氮唑分子轴的大的平面外变形。
• McLean, Gillian A.; Royles, Brodyck J. L.; Smith, David M., Journal of Chemical Research, Miniprint, 1996, # 10, p. 2623 - 2639
  作者：McLean, Gillian A.、Royles, Brodyck J. L.、Smith, David M.、Bruce, Michael J.

  DOI：——

  日期：——
• New chemical and biological aspects of artemisinin-Derived trioxane dimers
  作者：Gary H Posner、John Northrop、Ik-Hyeon Paik、Kristina Borstnik、Patrick Dolan、Thomas W Kensler、Suji Xie、Theresa A Shapiro

  DOI：10.1016/s0968-0896(01)00270-x

  日期：2002.1

  Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. H-1 NMR spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dinners 5a and 5b, are promising for chemotherapy of both malaria and cancer. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers
  作者：Gary H. Posner、Poonsakdi Ploypradith、Michael H. Parker、Hardwin O'Dowd、Soon-Hyung Woo、John Northrop、Mikhail Krasavin、Patrick Dolan、Thomas W. Kensler、Suji Xie、Theresa A. Shapiro

  DOI：10.1021/jm990363d

  日期：1999.10.1

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.