(cyclohex-1-enyl)methyl phenyl sulfone | 49639-03-4

• 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: (cyclohex-1-enyl)methyl phenyl sulfone
• 英文别名: 1-((phenylsulfonyl)methyl)cyclohexene；cyclohexenylmethyl(phenyl) sulfone；cyclohex-1-enylmethyl-phenyl sulfone；Cyclohex-1-enylmethyl-phenyl-sulfon；1-(Benzolsulfonylmethyl)-cyclohexen；Cyclohex-1-enyl-phenylsulfon；1-Cyclohexenyl-methylsulfonyl-benzene；cyclohexen-1-ylmethylsulfonylbenzene
• CAS: 49639-03-4
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: YERFJDXJJJDUOD-UHFFFAOYSA-N

物化性质

• 熔点：
  76.5-77 °C(Solv: acetic acid (64-19-7))
• 沸点：
  395.8±25.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (cyclohex-1-enyl)methyl phenyl sulfone 在 正丁基锂 、 三氯化铝 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Chemo-, regio-, and diastereoselective alkylation via Lewis acid promoted substitutions of sulfones

  摘要：

  DOI：

  10.1021/ja00265a050
• 作为产物：
  描述：

  苯甲砜 在 正丁基锂 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 生成 (cyclohex-1-enyl)methyl phenyl sulfone
  参考文献：
  名称：

  Chemo-, regio-, and diastereoselective alkylation via Lewis acid promoted substitutions of sulfones

  摘要：

  DOI：

  10.1021/ja00265a050

文献信息

• Neighboring Group Participation in the Halogenation of Sulfoxides
  作者：T. Durst、K.-C. Tin、M. J. V. Marcil

  DOI：10.1139/v73-256

  日期：1973.6.1

  PhS(O)(CH₂)_nCH₂OH(n = 1–3) react with sulfuryl chloride at −78° or 0° in methylene chloride to give the corresponding PhSO₂(CH₂)_nCH₂Cl. Evidence is presented that cyclic alkoxyoxosulfonium salts are intermediates in these transformations. When n = 4 only chlorination α to the sulfoxide function was observed. The sulfinyl carboxylic acids PhS(O)(CH₂)_nCO₂H (n = 1–3) and amides PhS(O)(CH₂)_nCONH₂ (n = 1–3) were also reacted with SO₂Cl₂. α-Chlorination was observed for both compounds when n = 1 or 3. When n = 2 the products were the 3-phenylsulfonylpropionyl chloride and 3-phenyl-sulfonylpropionitrile respectively.

  PhS(O)(CH₂)ₙCH₂OH(n = 1–3) 在氯化亚砜氯在−78°或0°的氯化亚砜中反应，得到相应的PhSO₂(CH₂)ₙCH₂Cl。有证据表明，环状烷氧氧代磺鎓盐是这些转化中间体。当n = 4时，只观察到对亚砜功能的α氯化。烷磺酰基羧酸PhS(O)(CH₂)ₙCO₂H (n = 1–3) 和酰胺PhS(O)(CH₂)ₙCONH₂ (n = 1–3) 也与SO₂Cl₂反应。当n = 1或3时，两种化合物均观察到α氯化。当n = 2时，产物分别为3-苯基磺酰基丙酰氯和3-苯基磺酰基丙腈。
• Scope and stereochemistry of an olefin synthesis from β-hydroxysulphones
  作者：Philip J. Kocienski、Basil Lythgoe、Steven Ruston

  DOI：10.1039/p19780000829

  日期：——

  The synthesis of olefins from β-acyloxy-sulphones by reduction with sodium amalgam in methanol–ethyl acetate can be applied to the preparation of a wide variety of conjugated dienes. When used for the synthesis of 1,2-disubstituted olefins in which the new double bond is either isolated or conjugated, the reaction is highly stereoselective, and leads to the trans-isomers.

  通过将钠汞齐在甲醇-乙酸乙酯中还原，由β-酰氧基砜合成烯烃的方法可用于制备多种共轭二烯。当用于合成其中新的双键被分离或共轭的1,2-二取代的烯烃时，该反应是高度立体选择性的，并导致反式异构体。
• Synthesis and reactivity of the 1,1-dilithio derivatives of alkyl phenyl sulfones and N,N-dimethyl methanesulfonamide
  作者：A. Bongini、D. Savoia、A. Umani-Ronchi

  DOI：10.1016/s0022-328x(00)89360-2

  日期：1976.5

  Alkyl phenyl sulfones Ia,b and N,N-dimethyl methanesulfonamide (Ic) are rapidly converted into their 1,1-dilithio salts IIa–c on reaction with n-butyllithium in THF—hexane. The nature of these new organometallic species was confirmed by deuteration and condensation with benzaldehyde. The gem-dimetallo derivatives Va–c and VIa, obtained from IIa–c by lithium—magnesium and lithium—boron exchange respectively

  与正丁基锂在THF-己烷中反应后，烷基苯基砜Ia，b和N，N-二甲基甲磺酰胺（Ic）迅速转化为1,1-二硫代盐IIa-c。通过氘化和与苯甲醛缩合证实了这些新的有机金属物种的性质。分别通过锂-镁和锂-硼交换从IIa-c获得的宝石双金属衍生物Va-c和VIa与羰基化合物反应生成α，β-不饱和砜VIIa-c和相应的β-羟基砜VIIIa- C。
• Regioselective Preparation of Allylic Sulfones by Palladium-Catalyzed Reactions of Allylic Nitro Compounds with Sodium Benzenesulfinate
  作者：Noboru Ono、Isami Hamamoto、Takashi Kawai、Aritsune Kaji、Rui Tamura、Masato Kakihana

  DOI：10.1246/bcsj.59.405

  日期：1986.2

  thermodynamically-stable isomers is negligible. On the other hand, the palladium-catalyzed sulfonylation of allylic acetates with sodium benzenesulfinate is accompanied by the isomerization to give the thermodynamically-controlled products selectively. These results can be explained by assuming that allylic nitro compounds are more reactive to the palladium catalyst than allylic acetates and sulfones.

  在 N,N-二甲基甲酰胺 (DMF) 中 5 mol% Pd(PPh3)4 存在下，在 20–70 °C 下，用苯亚磺酸钠处理烯丙基硝基化合物 1–10 小时，导致形成占优势的烯丙基砜动力学控制的产品。产物分布主要受烯丙基单元取代基的电子性质控制，异构化为热力学稳定的异构体可以忽略不计。另一方面，钯催化的乙酸烯丙酯与苯亚磺酸钠的磺酰化伴随异构化，选择性地得到热力学控制的产物。这些结果可以通过假设烯丙基硝基化合物比烯丙基乙酸酯和砜对钯催化剂更具反应性来解释。
• Chelation-Induced Catalytic Multiple Arylation of Allylic 2-Pyridyl Sulfones
  作者：Tomás Llamas、Ramón Gómez Arrayás、Juan Carlos Carretero

  DOI：10.1002/adsc.200404180

  日期：2004.12

  metal-catalyzed protocol for the sequential multiarylation of cyclic allyl sulfones is described. The metal-coordinating ability of the 2-pyridyl group on the sulfone promotes the otherwise difficult intermolecular Heck monoarylation and diarylation of trisubstituted alkenes, as well as the copper-catalyzed allylic arylation with Grignard reagents.

  描述了用于环烯丙基砜的顺序多芳基化的螯合辅助，过渡金属催化的方案的发展。砜上的2-吡啶基的金属配位能力促进了原本困难的三取代烯烃的分子间Heck单芳基化和二芳基化，以及用格氏试剂的铜催化的烯丙基芳基化。