3-chloro-2-(phenylsulfonyl)-1-propene | 90838-30-5

• 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: 3-chloro-2-(phenylsulfonyl)-1-propene
• 英文别名: 3-chloro-2-phenylsulfonyl-1-propene；3-Chloroprop-1-en-2-ylsulfonylbenzene
• CAS: 90838-30-5
• 化学式: C₉H₉ClO₂S
• 分子量: 216.688
• InChiKey: FYEJNOHOIOSQEN-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±34.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(phenylsulfonyl)-1-propene 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-<2-(phenylsulfonyl)-2-propenyl>phenylamine
  参考文献：
  名称：

  Yamamoto, Iwao; Kajiwara, Kouji; Fujimoto, Tetsuya, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 515 - 518

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-Dichloropropan-2-ylsulfanylbenzene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 90.0h， 生成 3-chloro-2-(phenylsulfonyl)-1-propene
  参考文献：
  名称：

  3-Chloro-2-(phenylsulfinyl)-1-propene and 3-chloro-2-(phenylsulfonyl)-1-propene: preparation and utility as reagents for .alpha.,.alpha.'-annelation of cyclic ketones

  摘要：

  DOI：

  10.1021/jo00191a017

文献信息

• New Insights into Structures, Stability, and Bonding of μ-Allyl Ligands Coordinated with Pd−Pd and Pd−Pt Fragments
  作者：Hideo Kurosawa、Kazuyoshi Hirako、Satoko Natsume、Sensuke Ogoshi、Nobuko Kanehisa、Yasushi Kai、Shigeyoshi Sakaki、Kaori Takeuchi

  DOI：10.1021/om950843c

  日期：1996.4.16

  1-phenyl, and 1-chloroallyl ligands on the Pd−Pd bond exist in an anti configuration almost exclusively. X-ray structure determinations of some of the μ-allyl Pd−Pd and Pd−Pt complexes, PdM(μ-allyl)(μ-X)(PPh3)2 (11, M = Pt, allyl = CH2C(COOMe)CH2, X = Br; 12, M = Pd, allyl = CH2C(COOMe)CH2, X = Br; 13, M = Pd, allyl = CH2CHCH(COOMe), X = SPh) were carried out. The crystal of 11 was isomorphous with

  由相应的烯丙基钯（II）氯化物与Pd（C 2）反应制备了一系列与Pd-Pd片段Pd 2（μ-烯丙基）（μ-Cl）（PPh 3）2配位的μ-烯丙基配体配合物。H 4）（PPh 3）2。所使用的μ-烯丙基配体在烯丙基骨架的末端或中心碳上都包含吸电子（Cl，CN，COOMe，SO 2 Ph）和给电子（Me，Ph）取代基。的取代的烯丙基配的相对能力来协调到PD（I）-Pd（I）片段VS单核Pd（II）片段是通过双核片段和单核片段之间的烯丙基配体交换平衡来确定的。带有较多吸取取代基的烯丙基配体比带有较少吸取取代基的烯丙基配体更强地与Pd-Pd片段配位。Pd-Pd键上的1-甲基，1-苯基和1-氯烯丙基配体几乎全部以反构型存在。某些μ-烯丙基Pd-Pd和Pd-Pt配合物PdM（μ-烯丙基）（μ-X）（PPh 3）2（11，M = Pt，烯丙基= CH 2 C（ COOMe）CH 2，X ＝ Br；12，M
• [3 + 2] Cyclization-elimination route to cyclopentenyl sulfones using (phenylsulfonyl)-1,2-propadiene
  作者：Albert Padwa、Philip E. Yeske

  DOI：10.1021/jo00022a032

  日期：1991.10

  Treatment of (phenylsulfonyl)-1,2-propadiene (1) with bis(phenylsulfonyl)methane in the presence of sodium hydride affords 2,4,4-tris(phenylsulfonyl)-1-butene in 94% yield. Similar rearranged products were obtained using other soft nucleophiles and related allenes. The formation of these products involves addition of benzenesulfinate anion onto allene 1. The initially formed carbanion undergoes proton transfer with bis(phenylsulfonyl)methane followed by a S(N)2' reaction of the resulting anion with 2,3-bis(phenylsulfonyl)-1-propene. Supporting evidence for the proposed mechanism is provided by the observation that the reaction of dimethyl malonate with the activated allene in the presence of sodium benzenesulfinate gives mostly abnormal products. When allene 1 is allowed to react with olefins bearing an electron-withdrawing group in the presence of sodium benzenesulfinate, a substituted cyclopentenyl sulfone is formed. The reaction proceeds in a stepwise fashion by addition of the initially produced carbanion onto the activated pi-bond of the olefin followed by a 5-endo-trig cyclization and elimination of benzenesulfinate. This approach represents a mild and versatile anionic [3 + 2] route to five-membered unsaturated sulfones.
• Synthesis of cyclopentenyl sulfones via the [3 + 2] cyclization-elimination reaction of (phenylsulfonyl)allene
  作者：Albert. Padwa、Philip E. Yeske

  DOI：10.1021/ja00213a042

  日期：1988.3
• ANZEVENO, P. B.;MATTHEWS, D. P.;BARNEY, CH. L.;BARBUCH, R. J., J. ORG. CHEM., 1984, 49, N 17, 3134-3138
  作者：ANZEVENO, P. B.、MATTHEWS, D. P.、BARNEY, CH. L.、BARBUCH, R. J.

  DOI：——

  日期：——
• PADWA, ALBERT;YESKE, PHILIP E., J. AMER. CHEM. SOC., 110,(1988) N 5, 1617-1618
  作者：PADWA, ALBERT、YESKE, PHILIP E.

  DOI：——

  日期：——