1-butyl-4-chloro-3-buten-1-yne | 157554-23-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-butyl-4-chloro-3-buten-1-yne
• 英文别名: (1Z)-1-chloro-oct-1-en-3-yne；1-chlorooct-1-ene-3-yne；(Z)-1-chloro-1-octen-3-yne；(Z)-1-chlorooct-1-en-3-yne
• CAS: 157554-23-9
• 化学式: C₈H₁₁Cl
• 分子量: 142.628
• InChiKey: AQNMFJNURQWNGG-FPLPWBNLSA-N

物化性质

• 沸点：
  170.3±23.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-butyl-4-chloro-3-buten-1-yne 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 11.5h， 生成 1-[(Z)-dec-3-ene-1,5-diynyl]-4-nitrobenzene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1002/1522-2675(200208)85:8<2564::aid-hlca2564>3.0.co;2-0
• 作为产物：
  描述：

  顺-1,2-二氯乙烯 以86%的产率得到
  参考文献：
  名称：

  Chemin Denis, Linstrumelle Gerard, Tetrahedron, 50 (1994) N 18, S 5335-5344

  摘要：

  DOI：

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。
• Double Anionic Cycloaromatization of 2-(6-Substituted-3-hexene-1,5-diynyl)benzonitriles Initiated by Methoxide Addition
  作者：Ming-Jung Wu、Chi-Fong Lin、Shang-Hung Chen

  DOI：10.1021/ol990137y

  日期：1999.9.1

  [reaction: see text] Treatment of 2-((3Z)-undecene-1,5-diynyl)benzonitrile with 5 equiv of sodium methoxide in refluxing methanol for 16 h gave 1-pentyl-6-methoxyphenanthridine in 12% yield, 1-pentyl-6-phenanthridone in 6% yield, and 2-(2-pentyl-6-methoxyphenyl)benzonitrile in 4% yield. Under the same reaction conditions, methanolysis of several other benzonitriles gave similar results. Phenanthridine

  [反应：请参见文本]用5当量的甲醇钠在回流的甲醇中处理2-（（3Z）-十一碳烯-1,5-二炔基）苄腈16小时，制得1-戊基-6-甲氧基菲啶，产率为12％，1 -戊基-6-菲啶酮的产率为6％，2-（2-戊基-6-甲氧基苯基）苄腈的产率为4％。在相同的反应条件下，其他几种苄腈的甲醇分解得到相似的结果。获得了菲啶和联苯衍生物作为主要产物。提出了一种新的烯二炔环芳化反应的机理。
• 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。
• A copper-mediated cyclization reaction of hydrazine with enediynones providing pyrazolo[1,5-a]pyridines
  作者：Hung-Chou Wu、Long-Chih Hwang、Ming-Jung Wu

  DOI：10.1039/c0ob00756k

  日期：——

  2,7-Disubstituted pyrazolo[1,5-a]pyridines were synthesized in good chemical yields by the reaction of enediynones with hydrazine, followed by addition of copper chloride. This reaction can tolerate many functional groups.

  通过烯二酮与二烯酮的反应合成了2,7-二取代的吡唑并[1,5- a ]吡啶，化学产率高。肼，然后添加 氯化铜。该反应可以耐受许多官能团。
• 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％。