but-3-enyl prop-2-ene-1-sulfonate | 38330-52-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: but-3-enyl prop-2-ene-1-sulfonate
• 英文别名: but-3-enyl prop-2-enesulfonate；but-3-enyl allylsulfonate
• CAS: 38330-52-8
• 化学式: C₇H₁₂O₃S
• 分子量: 176.236
• InChiKey: NSEKZZVHPNHQLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  but-3-enyl prop-2-ene-1-sulfonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 甲基(三氟甲基)-1,3-二环氧丙烷 、 disodium ethylenediamine tetraacetic acid 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2,2-dioxo-6,7-dihydro-5H-oxathiepin-5-ol
  参考文献：
  名称：

  Alkoxide-Directed Hydride Addition to α,β-Unsaturated Sultones

  摘要：

  Seven- and eight-membered beta,y-unsaturated sultones were readily prepared by ring closing metathesis. Epoxidation of these sultones and of an analogous six-membered sultone furnished the corresponding beta,gamma-epoxy sultones efficiently. Treatment of these epoxides with a suitable base gave alpha,beta-unsaturated gamma-hydroxy sultones in high yields. Reduction of both the alpha,beta-unsaturated sultones and the epoxy sultones by Red-Al is likely to proceed in a hydroxyl-directed fashion via a mixed aluminate as the reactive intermediate.

  DOI：

  10.3987/com-15-s(t)64
• 作为产物：
  描述：

  3-丁烯-1-醇 、 2-丙烯-1-磺酰氯 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以90%的产率得到but-3-enyl prop-2-ene-1-sulfonate
  参考文献：
  名称：

  用于制备磺内酯衍生物的闭环复分解 (RCM) 和金属催化的环丙烷化

  摘要：

  应用Grubbs催化剂2代作为催化剂的闭环复分解(RCM)制备了一系列高产率的新型不饱和磺内酯。使用二乙基锌/二碘甲烷或 Zn-Cu/二碘甲烷通过 Simmon-smith 环丙烷化将烯丙基磺内酯的环丙烷化应用了许多尝试，但在每种情况下均未形成相应的环状加合物。不饱和磺内酯与重氮乙酸乙酯的新型钯或优选铑催化的环丙烷化反应是通过过渡金属催化转移 CH-CO2Et 单元实现的。在低温（0-20℃）下，通过在6小时内向磺内酯和乙酸钯（II）或乙酸铑（II）二聚体的混合物中分批加入重氮乙酸乙酯来进行反应。在每种情况下都获得了所需的环丙烷化产物，

  DOI：

  10.24820/ark.5550190.p010.749

文献信息

• Synthesis of Sultones by Ring Closing Metathesis
  作者：Peter Metz、Sandra Karsch、Pia Schwab

  DOI：10.1055/s-2002-35560

  日期：——

  Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis of sulfonates. The required substrates were readily derived from alkenols and olefinic sulfonyl chlorides.

  通过磺酸盐的闭环复分解有效地合成了具有正常、中等和大环尺寸的不饱和磺内酯。所需的底物很容易从烯醇和烯属磺酰氯衍生而来。
• Ring Closing Metathesis in the Synthesis of Sultones and Sultams
  作者：Peter Metz、Sandra Karsch、Dirk Freitag、Pia Schwab

  DOI：10.1055/s-2004-822408

  日期：——

  synthesized by ring closing metathesis (RCM) of sulfonates. The resulting α,β-unsaturated sultones act as dienophiles in intermolecular Diels-Alder reactions. A first cyclic sulfate formation through RCM has been discovered, and a rapid access to p-lactams fused to a sultam moiety of variable ring size was developed from inexpensive, commercially available starting materials using RCM as the key operation

  通过磺酸盐的闭环复分解（RCM）有效地合成了具有正常、中等和大环尺寸的不饱和磺内酯。所得的 α,β-不饱和磺内酯在分子间 Diels-Alder 反应中充当亲双烯体。已经发现了通过 RCM 形成的第一个环状硫酸盐，并且使用 RCM 作为关键操作，从廉价的、可商购的起始材料开发了一种快速获得稠合到可变环大小的磺胺部分的 p-内酰胺的方法。还描述了一种有效的 4-vinyl-azetidin-2-ones 生成 1-aza-bicyclo[4.2.0]oct-4-en-8-ones 的 RCM。
• Flohic, Alexandre Le; Meyer, Christophe; Cossy, Janine, Synlett, 2003, # 5, p. 667 - 670
  作者：Flohic, Alexandre Le、Meyer, Christophe、Cossy, Janine、Desmurs, Jean-Roger、Galland, Jean-Christophe

  DOI：——

  日期：——
• Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole
  作者：Alexandre Le Flohic、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2006.07.010

  日期：2006.9

  Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, beta,gamma-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven-membered ring beta,gamma-unsaturated sultones were converted into homoallylic conjugated (Z)-dienols. This methodology was applied to the racemic synthesis of the originally proposed structure of the marine natural product mycothiazole. (c) 2006 Elsevier Ltd. All rights reserved.
• Ring closing metathesis and metal-catalyzed cyclopropanation for the preparation of sultone derivatives
  作者：Korany A. Ali、Peter Metz

  DOI：10.24820/ark.5550190.p010.749

  日期：——

  of novel unsaturated sultones with high yields. Many attempts, were applied for the cyclopropanation of the allylic sultones by Simmon-smith cyclopropanation using diethyl zinc/diiodomethane or Zn-Cu/diiodomethane but in each case the corresponding cyclic adduct was not formed. A novel palladium or preferably rhodiumcatalyzed cyclopropanation of unsaturated sultones with ethyl diazoacetate was achieved

  应用Grubbs催化剂2代作为催化剂的闭环复分解(RCM)制备了一系列高产率的新型不饱和磺内酯。使用二乙基锌/二碘甲烷或 Zn-Cu/二碘甲烷通过 Simmon-smith 环丙烷化将烯丙基磺内酯的环丙烷化应用了许多尝试，但在每种情况下均未形成相应的环状加合物。不饱和磺内酯与重氮乙酸乙酯的新型钯或优选铑催化的环丙烷化反应是通过过渡金属催化转移 CH-CO2Et 单元实现的。在低温（0-20℃）下，通过在6小时内向磺内酯和乙酸钯（II）或乙酸铑（II）二聚体的混合物中分批加入重氮乙酸乙酯来进行反应。在每种情况下都获得了所需的环丙烷化产物，