4-(benzylthio)-1-butyne | 148470-44-4

• 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: 4-(benzylthio)-1-butyne
• 英文别名: benzyl but-1-yn-4-yl sulfide；benzyl 3-butynyl sulfide；But-3-ynylsulfanylmethylbenzene
• CAS: 148470-44-4
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: ZLYSLRAZVSOXMB-UHFFFAOYSA-N

物化性质

• 沸点：
  267.4±23.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(benzylthio)-1-butyne 在 碘 、 间氯过氧苯甲酸 作用下， 生成 4,5-dihydro-3-iodothiophene 1,1-dioxide
  参考文献：
  名称：

  Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides

  摘要：

  The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent. Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts. The endo- versus exo-regioselectivity of these alkenyl sulfide ring closures most likely reflects the difference in thermodynamic stabilities of the beta-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate. The efficiency of the cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers. Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides. Conversely the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length. Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring, The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control. The methodology has been applied to the synthesis of unusual bicyclic beta-lactams related to the penicillin family of antibiotics.

  DOI：

  10.1021/jo00125a038
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.17h， 生成 4-(benzylthio)-1-butyne
  参考文献：
  名称：

  一锅法无硫醇合成硫化物和选择性亚砜

  摘要：

  报道了一种简便高效的无硫醇一锅法，用于在绿色条件下不使用任何金属催化剂直接合成硫化物和亚砜。为此，我们在硫代乙酸钾 (PTA) 和 Oxone® 的存在下使用苄基溴作为起始材料，这些都是低成本且易于获得的化学品。该方法与多种官能团高度相容，并以良好的收率提供了一系列硫化物、双硫化物和亚砜。通过一种机制讨论了亚砜在砜上的选择性形成。

  DOI：

  10.1039/d2ra04872h

文献信息

• [EN] SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS<br/>[FR] SYNTHESE DESTINEE A LA PREPARATION DE COMPOSES DE CRIBLAGE UTILISES COMME AGENTS DE FIXATION A LA TUBULINE
  申请人：UNIV AUSTRALIAN

  公开号：WO2002060872A1

  公开（公告）日：2002-08-08

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物以用作潜在的微管聚合抑制剂筛选的方法。本发明还提供了具有微管聚合抑制剂活性的化学化合物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4
  作者：Bernard L Flynn、Guy P Flynn、Ernest Hamel、M.Katherine Jung

  DOI：10.1016/s0960-894x(01)00436-x

  日期：2001.9

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Regiochemical studies on halocyclization reactions of unsaturated sulfides
  作者：Ren Xiao-Feng、Edward Turos

  DOI：10.1016/0040-4039(93)85010-t

  日期：1993.3
• Capella Laura, Montevecchi Pier Carlo, Nanni Daniele, J. Org. Chem, 59 (1994) N 12, S 3368- 3374
  作者：Capella Laura, Montevecchi Pier Carlo, Nanni Daniele

  DOI：——

  日期：——