5,5-bis(phenylsulfonyl)-1-octen-7-yne | 109432-98-6

• 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: 5,5-bis(phenylsulfonyl)-1-octen-7-yne
• 英文别名: 5,5-bis(phenylsulfonyl)oct-1-en-7-yne；6,6-bis(phenylsulfonyl)oct-7-en-1-yn；1,1'-(Oct-1-en-7-yne-5,5-diyldisulfonyl)dibenzene；4-(benzenesulfonyl)oct-7-en-1-yn-4-ylsulfonylbenzene
• CAS: 109432-98-6
• 化学式: C₂₀H₂₀O₄S₂
• 分子量: 388.508
• InChiKey: RXBUPDSRXUQNGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5-bis(phenylsulfonyl)-1-octen-7-yne 在 polymer supported nickel chromium dichloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 以80%的产率得到1,1'-[(3,4-Dimethylidenecyclohexane-1,1-diyl)disulfonyl]dibenzene
  参考文献：
  名称：

  A novel nickel-chromium catalyst system for cyclization via intramolecular carbametalation

  摘要：

  DOI：

  10.1021/ja00251a036
• 作为产物：
  描述：

  4,4-dicarbomethoxy-1,2-dimethylene cyclohexane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(邻甲基苯基)磷 作用下， 以 苯 为溶剂， 生成 5,5-bis(phenylsulfonyl)-1-octen-7-yne
  参考文献：
  名称：

  A new palladium catalyst for intramolecular carbametalations of enynes

  摘要：

  DOI：

  10.1016/s0040-4039(01)80273-2

文献信息

• Pd-catalyzed borylative cyclisation of 1,7-enynes
  作者：Virtudes Pardo-Rodríguez、Elena Buñuel、Daniel Collado-Sanz、Diego J. Cárdenas

  DOI：10.1039/c2cc34468h

  日期：——

  Reaction of a variety of 1,7-enynes with bis(pinacolato) diboron catalysed by Pd bis(trifluoroacetate) affords homoallylic and allylic boronates containing a six membered carbo- or heterocycle, by formation of C–C and C–B bonds

  多种1,7-炔烃与双（匹那可酯）二硼的反应在Pd双（三氟乙酸盐）的催化下，产生含有六个成员的碳环或杂环的同 allyl 和 allyl 硼酸盐，通过形成C–C和C–B键。
• Ruthenium-Catalyzed Domino Redox Bicycloisomerization. An Atom-Economical Synthesis of [3.1.0]- and [4.1.0]Carbo- and Heterocycles
  作者：Barry M. Trost、Adam W. Franz

  DOI：10.1021/ja1088452

  日期：2010.12.29

  Supporting Information Available: ESI-MS data of the reaction products formed upon addition of EDA to Co(TPP) and Co(3,5-DitBu-ChenPhyrin); DFT optimized geometries, SOMO and spin density plots of species trans-D; Tables containing ∆E, ∆EZPE, ∆G, ∆H and ∆S values of all DFT optimized geometries; free energies for olefin cyclopropanation at the b3-lyp, def-TZVP level; computed IR CO stretching frequencies

  可用的支持信息：将 EDA 添加到 Co(TPP) 和 Co(3,5-DitBu-ChenPhyrin) 后形成的反应产物的 ESI-MS 数据；DFT 优化几何、SOMO 和物种 trans-D 的自旋密度图；包含所有 DFT 优化几何形状的 ∆E、∆EZPE、∆G、∆H 和 ∆S 值的表格；b3-lyp、def-TZVP 水平的烯烃环丙烷化自由能；计算出的 IR CO 展宽频率。该材料可通过互联网免费提供，网址为 http://pubs.acs.org。
• Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System
  作者：Barry M. Trost、Donna L. Romero、Frode Rise

  DOI：10.1021/ja00089a016

  日期：1994.5

  The mechanisms by which palladium complexes may catalyze the cycloisomerization of 1,6- and 1,7-enynes to dialkylidenecycloalkanes were probed by exploring a catalyst system different than a ligated palladium acetate which previously has proven to be successful. Although carboxylic acids showed no discernible interaction with palladium(0) complexes, this combination proved to be a powerful catalyst system to effect this cycloisomerization. The fact that the two catalyst systems do not have the same reactivity profile suggests this new catalyst system may operate by a different mechanism. Evidence supporting a pathway invoking formation of a hydridopalladium acetate followed by hydropalladation as initiation is presented. Steric and electronic effects direct the regioselectivity of the termination step to form either 1,3- or 1,4-diene products. The 1,3-diene products participate exceedingly well in Diels-Alder reactions, both inter- and intramolecularly. The presence of an oxygen substituent at the position allylic to the diene served as both a regiochemical control element for the palladium-catalyzed cycloisomerization and a diastereochemical control element for the Diels-Alder reaction. The net result of these two steps, the first of which is a catalyzed isomerization and the second an addition, is a highly efficient approach to complex polycycles in terms of both selectivity and atom economy.
• Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes
  作者：Javier Adrio、Juan C. Carretero

  DOI：10.1021/ja0684186

  日期：2007.1.1

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.
• TROST, BARRY M.;LEE, DONNA C.;RISE, FRODE, TETRAHEDRON LETT., 30,(1989) N, C. 651-654
  作者：TROST, BARRY M.、LEE, DONNA C.、RISE, FRODE

  DOI：——

  日期：——