(3Z)-1-(trimethylsilyl)-dec-3-en-1,5-diyne | 155187-27-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3Z)-1-(trimethylsilyl)-dec-3-en-1,5-diyne
• 英文别名: 1-(trimethylsilyl)dec-3-ene-1,5-diyne；1-trimethylsilyl-dec-3-ene-1,5-diyne；[(Z)-dec-3-en-1,5-diynyl]-trimethylsilane
• CAS: 155187-27-2
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: VTIVBLVHIXVZGD-KHPPLWFESA-N

物化性质

• 沸点：
  247.4±19.0 °C(Predicted)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3Z)-1-(trimethylsilyl)-dec-3-en-1,5-diyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene
  参考文献：
  名称：

  （Z）-1-芳基-3-己烯-1，5-二炔与叠氮化钠的反应：1-芳基-1H-苯并三唑的合成。

  摘要：

  [反应：参见正文]通过（Z）-的处理，完成了涉及1,3-偶极环加成反应，阴离子环化和σ重排的新型串联级联反应，用于合成1-芳基-1H-苯并三唑2和3。 1-芳基-3-henen-1,5-二炔（1）与叠氮化钠在DMF或DMSO中在80摄氏度下反应12小时，收率65-91％。

  DOI：

  10.1021/ol047563q
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-1-trimethylsilylprop-1-yne 在 potassium hydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (3Z)-1-(trimethylsilyl)-dec-3-en-1,5-diyne
  参考文献：
  名称：

  Stereoselective synthesis of enediynes and enynes by condensation of aldehydes with γ-(trialkylsilyl)allenylboranes

  摘要：

  Enediynes and enynes with high geometric purity were synthesized by treating acetylenic and simple aldehydes with gamma-(tert-butyldimethylsilyl)allenylborane 2a followed by the elimination step of the Peterson olefination reaction.

  DOI：

  10.1016/s0040-4039(00)61341-2

文献信息

• Pharmaceutical compositions comprising aryl-substituted acyclic enediyne compounds
  申请人：Wu Ming-Jung

  公开号：US20050004211A1

  公开（公告）日：2005-01-06

  A pharmaceutical compositions comprises a compound of formula (I): or a pharmaceutically acceptable salt thereof: wherein R 1 ═R 2 ═H; or R 1 and R 2 together form a moiety represented by the formula R 3 represents a substituted or unsubstituted alkyl having 4-30 carbon atoms, or a substituted or unsubstituted aryl group having 3-30 carbon atoms; and R 4 represents a substituted or unsubstituted aryl group having 3-30 carbon atoms; with the proviso that R 3 is not butyl, pentyl, tetrahydropyranyloxymethyl, tetrahydropyranyloxypropyl or phenyl when R 1 ═R 2 ═H and R 4 is o-cyanophenyl,; and with the proviso that R 3 is not butyl when R 1 ═R 2 ═H and R 4 is phenyl. The pharmaceutical composition may be used to treat a subject afflicted with a tumor/cancer by inhibiting topoisomerase I activities or blocking the S phase or G 2 /M phase of the tumor/cancer cells.

  一种药物组合物包括化合物的结构式(I)：或其药用可接受的盐：其中R1=R2=H；或R1和R2一起形成由结构式表示的基团R3代表具有4-30个碳原子的取代或未取代的烷基，或具有3-30个碳原子的取代或未取代的芳基；和R4代表具有3-30个碳原子的取代或未取代的芳基；但R3不是丁基、戊基、四氢吡喃氧甲基、四氢吡喃氧丙基或苯基，当R1=R2=H和R4是邻氰基苯基时；且R3不是丁基，当R1=R2=H和R4是苯基时。该药物组合物可用于通过抑制拓扑异构酶I活性或阻断肿瘤/癌细胞的S期或G2/M期治疗患有肿瘤/癌症的受试者。
• Palladium-catalyzed reaction of (E) and (Z)-dichloroethenes with 1-alkynes. An efficient stereospecific synthesis of (E) and (Z)-enediynes.
  作者：Denis Chemin、Gerard Linstrumelle

  DOI：10.1016/s0040-4020(01)80691-8

  日期：1994.5

  The stereospecific sequential substitution of (E) and (Z)-dichloroethenes with 1-alkynes leads to (E) and (Z)-enediynes in high yield.

  （E）和（Z）-二氯乙烯被1-炔的立体有序顺序取代导致高产率的（E）和（Z）-二烯炔。
• Synthesis of Carbazoles via an Intramolecular Cyclization of 2-(6-Substituted 3(<i>Z</i>)-hexen-1,5-diynyl)anilines and Their Related Molecules
  作者：Chia-Ying Lee、Chi-Fong Lin、Jeng-Lin Lee、Ching-Chen Chiu、Wen-Der Lu、Ming-Jung Wu

  DOI：10.1021/jo0303158

  日期：2004.3.1

  Various 2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines 1a−g were treated with potassium tert-butoxide or potassium 3-ethylpentanoxide in NMP at 60 °C for 2 h to give the corresponding 5-substituted carbazoles 2a−g in 36−65% yields together with indoles 9a−g in 21−40% yields, respectively. Exposing the trifluoroacetamide analogues 10h−k under the same reaction conditions gave the carbazoles 2b−e in 37−57%

  将各种2-（6-取代的3（Z）-己烯-1,5-二炔基）苯胺1a - g在60°C的NMP中用叔丁醇钾或3-乙基五氧化钾处理2 h，得到相应的5取代的咔唑2a - g的产率为36-65％，吲哚9a - g的产率为21-40％。在相同反应条件下暴露三氟乙酰胺类似物10h - k得到咔唑2b - e，收率为37-57％，吲哚9b - e收率为15-27％。随后乙酰胺类似物10a - g的环化反应产生咔唑2a - g，收率53-86％。
• Cytotoxicities and Topoisomerase I Inhibitory Activities of 2-[2-(2-Alkynylphenyl)ethynyl]benzonitriles, 1-Aryldec-3-ene-1,5-diynes, and Related Bis(enediynyl)arene Compounds
  作者：Chi-Fong Lin、Wen-Der Lu、Pei-Chen Hsieh、Yao-Haur Kuo、Huey-Fen Chiu、Chyi-Jia Wang、Ming-Jung Wu

  DOI：10.1002/1522-2675(200208)85:8<2564::aid-hlca2564>3.0.co;2-0

  日期：2002.8

  The activities of a series of acyclic enediynes, 2-(6-substituted hex-3-ene-1,5-diynyl)benzonitriles (1-5) and their derivatives 7-23 were evaluated against several solid tumor cell lines and topoisomerase I. Compounds 1-5 show selective cytotoxicity with Hepa cells, and 2-[6-phenylhex-3-ene-1,5-diynyl]benzonitrile (5) reveals the most-potent activity. Analogues 8-10 and 13-22 also have the same effect with DLD cells; 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene 21 shows the highest activity among them. Moreover, 1-[(Z)-dec-3-ene-1,5-diynyl]2-(trifluoromethyl)benzene (20) exhibits the strongest inhibitory activity with the Hela cell line. Derivatives 9, 10, 18, and 23 display inhibitory activities with topoisomerase I at 87 mum. The cell-cycle analysis of compound 5, which induces a significant blockage in S phase, indicates that these novel enediynes probably undergo other biological pathways leading to the cytotoxicity, except the inhibitory activity toward topoisomerase I.
• A Route to 5-Substituted Dibenzofurans by Anionic Cycloaromatization of 2-(6-substituted 3-hexen-1,5-diynyl)phenyl tert-butyldimethyl ethers and Related Molecules
  作者：Ming-Jung Wu、Chia-Ying Lee、Chi-Fong Lin

  DOI：10.1002/1521-3773(20021104)41:21<4077::aid-anie4077>3.0.co;2-z

  日期：2002.11.4