1-chloro-4-trimethylsilyl-buten-3-yne | 102139-32-2

• 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: 1-chloro-4-trimethylsilyl-buten-3-yne
• 英文别名: (4-Chlorobut-3-en-1-yn-1-yl)(trimethyl)silane；4-chlorobut-3-en-1-ynyl(trimethyl)silane
• CAS: 102139-32-2
• 化学式: C₇H₁₁ClSi
• 分子量: 158.703
• InChiKey: FWNINWVPFCYDMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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-chloro-4-trimethylsilyl-buten-3-yne 、 2-乙炔基苯甲腈 以to form 2-(6-trimethylsilyl-3-hexen-1,5-diynyl)benzonitrile, which的产率得到2-[6-(Trimethylsilyl)hex-3-ene-1,5-diyn-1-yl]benzonitrile
  参考文献：
  名称：

  Aryl-substituted acyclic enediyne compounds

  摘要：

  本发明提供了式（I）的芳基取代的无环炔二烯化合物或其药学上可接受的盐或溶剂，其中R1═R2═H；或R1和R2结合形成由式表示的基团R3，其中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基团；而R代表具有3-30个碳原子的取代或未取代的芳基基团；但是当R1═R2═H且R4为o-氰基苯基时，R3不是丁基，戊基，四氢吡喃氧甲基，四氢吡喃氧丙基或苯基；而当R1═R2═H且R4为苯基时，R3不是丁基。发现式（I）的化合物具有抑制拓扑异构酶I的活性或作为S期或G2/M期阻滞剂的活性。

  公开号：

  US20050004212A1
• 作为试剂：
  描述：

  4-(tert-butyldimethylsilyloxy)methyl-1,3,3-trimethyl-2-(2-methyloxymethoxy-3-butynyl)cyclohex-1-ene 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 、 1-chloro-4-trimethylsilyl-buten-3-yne 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以69%的产率得到bis-4-(tert-butyldimethylsilyloxy)methyl-1,3,3-trimethyl-2-(2-methyloxymethoxy-3-butynyl)cyclohex-1-ene
  参考文献：
  名称：

  Taxamycins: a new enediyne family with synthetic and biological potential

  摘要：

  基于Pd(0)的合成方法合成了两种二硅基合成物（Z-1-三甲基硅基-6-叔丁基二苯基硅基己-3-烯-1,5-二炔（18）和Z-1-三甲基硅基-6-三异丙基硅基己-3-烯-1,5-二炔（19）），并描述了对三甲基硅基基团的选择性去除（K₂CO₃，MeOH），得到24和25。这些构建块用于合成紫杉醇-12类化合物38（16,17,18-三甲基-2-甲氧甲氧基-9-羟基双环[9.3.1]十五烯-5-烯-3,7-二炔）。最终的12元环闭合反应利用了碘代炔烃37（1,3,3-三甲基-2-(2-氧乙基)-4-(Z-1-甲氧甲氧基-7-碘庚-4-烯-2,6-二炔基)环己烯）的分子内Cr-Ni介导缩合。关键词：癌症、二炔烃、合成、Pd(0)偶联。

  DOI：

  10.1139/v95-279

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式(I)的化合物或其药学上可接受的盐：其中R1═R2═H; 或R1和R2一起形成由式表示的基团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基团; 和R4代表具有3-30个碳原子的取代或未取代的芳基基团; 前提是当R1═R2═H且R4为o-氰基苯基时，R3不是丁基，戊基，四氢吡喃氧甲基，四氢吡喃氧丙基或苯基; 前提是当R1═R2═H且R4为苯基时，R3不是丁基。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期来治疗患有肿瘤/癌症的受试者。
• Dynemicin analogs: syntheses, methods of preparation and use
  申请人：The Scripps Research Institute

  公开号：US05276159A1

  公开（公告）日：1994-01-04

  A fused ring system compound is disclosed that contains an epoxide group on one side of the fused rings and an enediyne macrocyclic ring on the other side of the fused rings. The compounds have DNA-cleaving, antimicrobial and tumor growth-inhibiting properties. Chimeric compounds having the fused ring system compound as an aglycone bonded to (i) a sugar moiety as the oligosaccharide portion or (ii) a monoclonal antibody or antibody combining site portion thereof that immunoreacts with target tumor cells are also disclosed. Compositions containing a compound or a chimer are disclosed, as are methods of preparing a compound.

  本发明揭示了一种融合环系统化合物，该化合物在融合环的一侧含有环氧基团，在另一侧含有烯二炔大环环。该化合物具有DNA裂解、抗微生物和抑制肿瘤生长的特性。本发明还揭示了具有融合环系统化合物作为无糖基部分的配体与（i）糖基部分或（ii）单克隆抗体或其抗体结合位点部分结合的嵌合化合物，其与目标肿瘤细胞免疫反应。揭示了含有化合物或嵌合物的组合物，以及制备化合物的方法。
• Dynemicin analogs: synthesis, methods of preparation and use
  申请人：The Scripps Research Institute

  公开号：US05281710A1

  公开（公告）日：1994-01-25

  A fused ring system compound is disclosed that contains an epoxide group on one side of the fused rings and an enediyne macrocyclic ring on the other side of the fused rings. The compounds have DNA-cleaving, antimicrobial and tumor growth-inhibiting properties. Chimeric compounds having the fused ring system compound as an aglycone bonded to (i) a sugar moiety as the oligosaccharide portion or (ii) a monoclonal antibody or antibody combining site portion thereof that immunoreacts with target tumor cells are also disclosed. Compositions containing a compound or a chimer are disclosed, as are methods of preparing a compound.

  本发明涉及一种融合环系统化合物，其在融合环的一侧含有环氧基团，在另一侧含有烯二炔大环环。该化合物具有DNA切割、抗微生物和抑制肿瘤生长的性质。本发明还公开了具有融合环系统化合物作为无糖基部分（i）或与目标肿瘤细胞免疫反应的单克隆抗体或抗体结合位部分（ii）结合的嵌合化合物。本发明还公开了含有化合物或嵌合物的组合物，以及制备化合物的方法。
• Conformational Control in Activation of an Enediyne
  作者：M. F. Semmelhack、Lingyun Wu、Robert A. Pascal、Douglas M. Ho

  DOI：10.1021/ja036763e

  日期：2003.9.1

  In the bicyclo[7.3.1]tridec-4-ene-2,6-diyne framework characteristic of calicheamicin, DFT calculations predict that the chair conformer should be much more reactive toward cycloaromatization compared to the boat form. A functionalized derivative of this framework with an added two-atom bridge to enforce the boat conformation was synthesized and shown to be stable at 23 degrees C. Cleavage of the bridge releases the conformational lock and cycloaromatization proceeds with t1/2 42.5 min/23 degrees C, presumably through the chair conformation. This confirms the prediction based on computation and points to a new principle for triggering the enediyne toxins.
• Concave Butterfly-Shaped Organometallic Hydrocarbons?
  作者：Matthew Laskoski、Gaby Roidl、Mark D. Smith、Uwe H. F. Bunz

  DOI：10.1002/1521-3773(20010417)40:8<1460::aid-anie1460>3.0.co;2-q

  日期：2001.4.17

  A metamorphosis of the tetraethynyl precursor 1 through double Cu-catalyzed ring closure leads to the corresponding butterfly-shaped cyclobutadiene complexes 2 in high yield (94 %). Single-crystal X-ray diffraction shows that the large organic ligand is distinctly nonplanar with a concave topology. Cp=cyclopentadiene.