1-phenylsulfonyl-3,4-dimethylcyclohex-3-ene | 73301-14-1

• 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: 1-phenylsulfonyl-3,4-dimethylcyclohex-3-ene
• 英文别名: 1,2-dimethyl-4-(phenylsulfonyl)cyclohexene；(3,4-Dimethylcyclohex-3-ene-1-sulfonyl)benzene；(3,4-dimethylcyclohex-3-en-1-yl)sulfonylbenzene
• CAS: 73301-14-1
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: LXZILNWNROCVCM-UHFFFAOYSA-N

物化性质

• 熔点：
  79.5-81.0 °C
• 沸点：
  402.9±38.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-phenylsulfonyl-3,4-dimethylcyclohex-3-ene 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.5h， 以76%的产率得到1,2-二甲基环己烯
  参考文献：
  名称：

  Dienophilic properties of phenyl vinyl sulfone and trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their utilization as synthons for ethylene, 1-alkenes, acetylene, and monosubstituted alkynes in the construction of functionalized six-membered rings via [4 + 2] .pi. cycloaddition methodology

  摘要：

  DOI：

  10.1021/jo00173a039
• 作为产物：
  描述：

  苯基溴代乙基硫醚 在 双氧水 、 sodium ethanolate 、 对苯二酚 作用下， 以 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 30.33h， 生成 1-phenylsulfonyl-3,4-dimethylcyclohex-3-ene
  参考文献：
  名称：

  Dienophilic properties of phenyl vinyl sulfone and trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their utilization as synthons for ethylene, 1-alkenes, acetylene, and monosubstituted alkynes in the construction of functionalized six-membered rings via [4 + 2] .pi. cycloaddition methodology

  摘要：

  DOI：

  10.1021/jo00173a039

文献信息

• A catalytic version of hypervalent aryl-λ³-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant
  作者：Kazunori Miyamoto、Yuuta Sakai、Shunsuke Goda、Masahito Ochiai

  DOI：10.1039/c2cc16360h

  日期：——

  The first catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides, which probably involves in situ generation of a tetracoordinated bis(aqua)(hydroxy)phenyl-λ3-iodane complex as an active oxidant from a catalytic amount of iodobenzene by the reaction with m-chloroperbenzoic acid in the presence of HBF4 in dichloromethane–water under mild conditions, was developed.

  首次开发出了基于超价芳基-λ³-碘烷引发的一级羧酰胺霍夫曼重排反应的催化版本，该方法可能涉及在温和条件下，在二氯甲烷-水体系中，通过催化量的碘苯与间氯过氧苯甲酸在含HBF₄的存在下反应，原位生成四配位的双(水合)(羟基)苯基-λ³-碘烷复合物作为活性氧化剂。
• Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Using <i>m</i>-Chloroperbenzoic Acid as a Terminal Oxidant
  作者：Kazunori Miyamoto、Yoshihisa Sei、Kentaro Yamaguchi、Masahito Ochiai

  DOI：10.1021/ja808829t

  日期：2009.2.4

  Transition metal-catalyzed oxidative cleavage of carbon-carbon multiple bonds has emerged as a powerful tool in organic synthesis. High-valent oxometals, mostly of Ru, Os, Mn, Mo, W, and Re, were used catalytically as reactive oxygen transfer agents to the multiple bonds. Reported here for the first time are the organocatalytic versions of the oxidative cleavage reactions. Our method involves use of

  过渡金属催化的碳-碳多键氧化裂解已成为有机合成中的有力工具。高价含氧金属，主要是 Ru、Os、Mn、Mo、W 和 Re，被用作催化多键的活性氧转移剂。这里首次报道了氧化裂解反应的有机催化版本。我们的方法涉及使用碘代三甲苯作为有效的有机催化剂，在无金属条件下生成活性芳基（羟基）-λ（3）-碘烷 5 和间氯过苯甲酸（m-CPBA）作为末端氧化剂。环状和无环烯烃以及脂肪族和芳香族炔烃在有机催化条件下顺利裂解为羧酸。
• Oxidative desulfonylation. Phenyl vinyl sulfone as a ketene synthetic equivalent
  作者：R.Daniel Little、Sun Ok Myong

  DOI：10.1016/s0040-4039(00)78683-7

  日期：1980.1

  α-Sulfonyl carbanions undergo oxidative desulfonylation to form ketones upon treatment with molybdenum peroxide MoO5·Py·HMPA (MoOPH) in THF at −78°C.

  在-78°C下用过氧化钼MoO 5 ·Py·HMPA（MoOPH）在THF中处理后，α-磺酰基碳负离子进行氧化脱磺酰化反应生成酮。
• An ethylene and terminal olefin equivalent in [4 + 2] .pi. cycloadditions. General synthetic application of phenyl vinyl sulfone to the construction of functionalized six-membered rings
  作者：Richard V. C. Carr、Leo A. Paquette

  DOI：10.1021/ja00522a075

  日期：1980.1
• A structure–taste study of arylsulfonyl(cyclo)alkanecarboxylic acids
  作者：Violetta Lysiak、Aleksander Ratajczak、Agnieszka Mencel、Krystyna Jarzembek、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2004.10.056

  日期：2005.2

  A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds 14 containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.