5-(p-tolylsulfonyl)-2-methyl-2,3-pentadiene | 157944-99-5

• 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-(p-tolylsulfonyl)-2-methyl-2,3-pentadiene
• 英文别名: 5-(p-toluenesulfonyl)-2-methyl-2,3-pentadiene
• CAS: 157944-99-5
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: RKGSWFMJQVSYAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chloropyridinecobaloxime(III) 、 5-(p-tolylsulfonyl)-2-methyl-2,3-pentadiene 在 Na(Hg) 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到1-[(pyridine)bis(dimethylglyoximato)cobaltio(III)]-4-methyl-2,3-pentadiene
  参考文献：
  名称：

  Stokes, Heather L.; Matthew Richardson; Wright, Marcus W., Organometallics, 1995, vol. 14, # 12, p. 5520 - 5532

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1-乙氧基乙氧基)-3-甲基丁-1-炔 在 氢氧化钾 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.75h， 生成 5-(p-tolylsulfonyl)-2-methyl-2,3-pentadiene
  参考文献：
  名称：

  Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions

  摘要：

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.

  DOI：

  10.1021/ja00094a037

文献信息

• Preparation of η1-1,3-dienyl, η1-1,2-dienyl and η3-cyclobutenone complexes via reactions of transition-metal carbonyl containing anions with allenic electrophiles
  作者：Heather L. Stokes、Terrence L. Smalley、Michelle L. Hunter、Mark E. Welker、Arnold L. Rheingold

  DOI：10.1016/0020-1693(94)03883-x

  日期：1994.6

  Abstract The preparation and reaction chemistry of 1,3- and 1,2-diene and related complexes derived from metal carbonyl containing anions and allenic electrophiles are addressed. The preparation of some CpFe(CO) 2 η 1 -diene complexes and their conversion into CpFe(CO) η 3 -diene complexes is presented followed by reactions of CpMo(CO) 3 − , CpW(CO) 3 − and CpMo(CO) 2 PR 3 − anions with allenic electrophiles

  摘要讨论了由含羰基金属的阴离子和烯丙基亲电试剂衍生的1，3-和1，2-二烯及相关配合物的制备和反应化学。介绍了一些CpFe（CO）2η1-二烯配合物的制备及其转化为CpFe（CO）η3-二烯配合物，然后进行了CpMo（CO）3-，CpW（CO）3-和CpMo（CO）反应）2 PR 3-具有烯丙基亲电试剂的阴离子，它们分别生成金属络合的环丁烯酮（通过最初形成的产物中的CO和烯烃插入）和1,2-二烯络合物。最后，概述了PPh 3（CO）3 Co-阴离子与烯丙型亲电试剂的反应，根据所使用的反应条件，会导致几种不同的配位几何形状。
• Preparation and Characterization of Molybdenum Tris(pyrazolyl)borate Dicarbonyl η³-Dienyl Complexes
  作者：Dean R. Lantero、Anne G. Glenn、Cynthia S. Day、Mark E. Welker

  DOI：10.1021/om030114u

  日期：2003.5.1

  Treatment of allenic electrophiles with Mo(CO)(3)(py)(3) followed by potassium hydrotris(l-pyrazolyl)borate (KTp) or treatment of an enyne with TpMo(CO)(3)H followed by decarbonylation cleanly produced stable, new eta(3)-dienyl complexes.
• General Preparation of Cyclopentadienyl Molybdenum Dicarbonyl η³-2-Alkylidene Cyclobutanonyl Complexes
  作者：N. Ariane Vinson、Cynthia S. Day、Mark E. Welker、Ilia Guzei、Arnold L. Rheingold

  DOI：10.1021/om990070i

  日期：1999.5.1

  Cyclopentadienylmolybdenumdicarbonyl anion reacts with a variety of allenic electrophiles to produce eta(3)-2-alkylidene cyclobutanoyl complexes. Three of these complexes have been. characterized by X-ray crystallography, and the 2-alkylidene cyclobutanone has been removed and recovered from one complex via oxidative demetalation.
• Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions
  作者：Marcus W. Wright、Terrence L. Smalley、Mark E. Welker、Arnold L. Rheingold

  DOI：10.1021/ja00094a037

  日期：1994.7

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.
• Stokes, Heather L.; Matthew Richardson; Wright, Marcus W., Organometallics, 1995, vol. 14, # 12, p. 5520 - 5532
  作者：Stokes, Heather L.、Matthew Richardson、Wright, Marcus W.、Vaughn, Stacia M.、Welker, Mark E.、Liable-Sands, Louise、Rheingold, Arnold L.

  DOI：——

  日期：——