4-(Benzenesulfonyl)hepta-1,6-dien-4-ylsulfonylbenzene | 100780-25-4

• 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-(Benzenesulfonyl)hepta-1,6-dien-4-ylsulfonylbenzene
• CAS: 100780-25-4
• 化学式: C₁₉H₂₀O₄S₂
• 分子量: 376.497
• InChiKey: DSITUZFGKDFLIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C(Solv: ethanol (64-17-5))
• 沸点：
  583.7±50.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  4-(Benzenesulfonyl)hepta-1,6-dien-4-ylsulfonylbenzene 在 iron(III) chloride 、 sodium tetrahydroborate 、 air 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以74%的产率得到1-chloromethyl-2-methyl-4,4-bis(phenylsulfonyl)cyclopentane
  参考文献：
  名称：

  Iron-Catalyzed Redox Radical Cyclizations of 1,6-Dienes and Enynes

  摘要：

  Treatment of 1,6-dienes and enynes with FeCl3 or Fe(Pc) in the presence of NaBH4 and air or O-2 causes radical cyclization to give five-membered carbo or heterocyclic compounds, Into which a halogen atom or hydroxyl group was introduced.

  DOI：

  10.1021/ol902562j
• 作为产物：
  描述：

  烯丙基甲基碳酸酯 、 双苯磺酸甲烷 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以94%的产率得到4-(Benzenesulfonyl)hepta-1,6-dien-4-ylsulfonylbenzene
  参考文献：
  名称：

  钌催化的1，3-二羰基化合物的一锅双烯丙基化/环异构化反应，生成外亚甲基环戊烷。

  摘要：

  钌催化的1，3-二酮和乙酰乙酸甲酯的一锅双烯丙基化/环异构化反应以中等到良好的收率得到了高亚甲基环戊烷的异构体选择性。双重烯丙基化步骤在Ru（II）预催化剂[Cp * RuCl（cod）]存在下于1,2-二氯乙烷中于90摄氏度下有效地进行。随后的环异构化反应是在加入三乙基硅烷作为氢化物后进行的。源，无需纯化1,6-二烯中间体。通过（1）NMR光谱对反应进行的详细检查显示，三乙基甲硅烷基甲基醚对于将在双烯丙基化步骤中形成的钌（IV）烯丙基络合物转化成环异构化所需的钌（II）物种起着重要作用。

  DOI：

  10.1002/chem.200305340

文献信息

• Addition-cyclization catalysed by palladium(II)
  作者：Barry M. Trost、Kevin Burgess

  DOI：10.1039/c39850001084

  日期：——

  Palladium catalysed nucleophilic additions to 1,6-dienes and a 1,6-enyne lead to cyclization in preference to β-hydrogen insertion; a novel cyclization of a 1,6-enyne to a 1,2-dimethylenecyclopentane is also reported.

  钯催化的1,6-二烯和1,6-烯炔的亲核加成反应优先于β-氢插入而导致环化。还报道了从1，6-烯炔到1，2-二亚甲基环戊烷的新型环化。
• Iron-Mediated Radical Nitro-Cyclization Reaction of 1,6-Dienes
  作者：Tsuyoshi Taniguchi、Hiroyuki Ishibashi

  DOI：10.1021/ol902510p

  日期：2010.1.1

  involved radical addition of a nitro group to 1,6-dienes promoted by the thermal decomposition of iron nitrate(III) nonahydrate, cyclization, and trapping of the resulting terminal radicals by a chlorine atom in the presence of chloride salt afforded five-membered-ring compounds. The present reaction provides a practical method for the synthesis of nitro compounds due to its simple experimental procedure

  依次进行的步骤包括：通过硝酸铁（III）九水合物的热分解，环化和在氯化物盐的存在下用氯原子捕获最终的末端自由基，将硝基基团加成至1,6-二烯。元环化合物。本反应由于其简单的实验步骤和使用无毒且廉价的铁试剂而为合成硝基化合物提供了一种实用的方法。
• Koteswar Rao, Y.; Nagarajan, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1031 - 1033
  作者：Koteswar Rao, Y.、Nagarajan, M.

  DOI：——

  日期：——
• Ruthenium(II)-Catalyzed Isomer-Selective Cyclization of 1,6-Dienes Leading to <i>e</i><i>xo</i>-Methylenecyclopentanes:  Unprecedented Cycloisomerization Mechanism Involving Ruthenacyclopentane(hydrido) Intermediate
  作者：Yoshihiko Yamamoto、Yu-ichiro Nakagai、Naoki Ohkoshi、Kenji Itoh

  DOI：10.1021/ja010134s

  日期：2001.7.1

  In the presence of a catalytic amount of ruthenium(II) complexes, [RuCl2(cod)](n), RuCl2(cod)(MeCN)(2), [RuCl2(nbd)](n). [RuCl2(CO)(3)](2), and Cp*Ru(cod)Cl, 1,6-dienes were effectively converted into the corresponding exo-methylenecyclopentanes in good to excellent yields with good isomer purity in i-PrOH at 90 degreesC. The alcoholic solvent was essential for the present catalytic cyclization, and the efficiency increased in the following order: t-BuOH << EtOH less than or equal to i-PrOH. In contrast, a Ru(0) complex. (C6Me6)Ru(cod), catalyzed the cycloisomerization only in 1,2-dichloroethane. The unusual isomer-selectivity occurred when a 1,7-octadiene was subjected to cyclization to give a similar exo-methylenecyclopentane isomer as the major product. The identical isomer selectivity was observed for the cyclization of unsymmetrical 1,6-dienes having one terminal- and one internal-alkene termini. On the basis of the results from the studies using the known ruthenium hydrides and deuterium-labeling substrates, the novel mechanism via the Ru(II) <--> Ru(IV) system involving a ruthenacyclopentane(hydrido) intermediate was proposed, which better explains the particular regiochemistry of the present cyclization than other previous mechanisms.
• RAO, Y. KOTESWAR;NAGARAJAN, M., INDIAN J. CHEM., 25,(1986) N 10, 1031-1033
  作者：RAO, Y. KOTESWAR、NAGARAJAN, M.

  DOI：——

  日期：——