3-Methylthio-1-cyclohexene | 34046-61-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-Methylthio-1-cyclohexene
• 英文别名: cyclohex-2-enyl-methyl sulfide；Cyclohex-2-enyl-methyl-sulfid；(+/-)-3-Methylmercapto-cyclohexen-(1)；Cyclohex-2-enyl-methylsulfid；3-Methylthio-1-cyclohexen；3-Methylsulfanylcyclohexene
• CAS: 34046-61-2
• 化学式: C₇H₁₂S
• 分子量: 128.238
• InChiKey: GEBPBCHGSBJMFB-UHFFFAOYSA-N

物化性质

• 沸点：
  155 °C
• 密度：
  0.960 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methylthio-1-cyclohexene 在 cesium fluoride 作用下， 以 乙二醇二甲醚 、 苯 为溶剂， 反应 40.0h， 生成 methyl(cyclohex-2-enyl)methyl sulfide
  参考文献：
  名称：

  Stereodirecting effect of a substrate methoxy substituent on the addition of singlet methylene to a double bond

  摘要：

  The stereodirecting effects of substrate methoxy, hydroxy, methylthio, and methyl substituents were examined in the addition of 1:CH2 to the double bonds of substrates 1a-d. The carbene, generated by photolysis of CH2N2, inserted into the C-H bonds of solvent and substrate, added to the substrate double bond to give products 2a-d, and attacked the oxygen or sulfur atom of substrates 1a-c to produce ylide intermediates which underwent 2,3-sigmatropic rearrangement to give products 3a-c. A preference for addition syn to the methoxy group of substrate 1a was observed when the reaction was run in pentane solution (syn-2a/anti-2a, 1.14 +/- 0.02), while a preference for formation of anti-2a was observed in diethyl ether solution (syn-2a/anti-2a, 0.92 +/- 0.03). A preference for 1:CH2 addition anti to the substrate substituent was observed for substrates 1b-d in both pentane and ether solution. The effect of the methoxy substituent was also examined in the addition of 1:CH2 to syn-7-methoxynorbornene (5b). Explanations for the substituent effects are offered based on both steric hindrance and interaction between 1:CH2 and the substituent, including formation and subsequent reaction of the ylide intermediates.

  DOI：

  10.1021/jo00075a016
• 作为产物：
  描述：

  ((Z)-6,6-Bis-methylsulfanyl-hex-1-enyl)-trimethyl-silane 在 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以37%的产率得到3-Methylthio-1-cyclohexene
  参考文献：
  名称：

  Dimethylmethylthiosulfonium fluoroborate. A chemoselective initiator for thionium ion induced cyclizations

  摘要：

  DOI：

  10.1021/ja00411a058

文献信息

• Reactions of Alkylthio Derivatives of Aluminum with Aldehydes, Ketones, and Olefins
  作者：J. M. Lalancette、Y. Beauregard、M. Bhéreur

  DOI：10.1139/v71-497

  日期：1971.9.15

  The preparation of ((CH₃)₂CHS)₂AlCH₃ and (t-CaH₉S)₂AlCH₃ is reported. The reactions of (RS)₂AlCH₃ (R = CH₃, (CH₃)₂CH, t-C₄H₉) with ketones give aldol condensations leading to the corresponding conjugated ketones, with the acetyl group R—CO—CH₃; with other ketones, a mixture of thioacetal and enolthioether is obtained. With aldehydes, a mixture of thioacetal and enolthioether is observed. With olefins there is an addition of two RS groups on the site of the double bond, with a small percentage of allylic substitution. With conjugated ketone, the saturated ketone is obtained with the alkylthio group in β position. All those reactions proceed with good yields and appear quite general.

  (CH3)2CHS)2AlCH3和(t-C4H9S)2AlCH3的制备已报道。(RS)2AlCH3 (R = CH3, (CH3)2CH, t-C4H9)与酮的反应产生醛缩反应，形成相应的共轭酮，带有乙酰基R—CO—CH3；与其他酮反应，得到硫缩醛和烯硫醚的混合物。与醛反应，观察到硫缩醛和烯硫醚的混合物。与烯烃反应，双键位置上发生两个RS基团的加成，少量的烯丙基取代。与共轭酮反应，饱和酮在β位得到烷硫基。所有这些反应都具有良好的产率，并且似乎相当普遍。
• METHOD FOR PRODUCING CYCLOALKYL ALKYL ETHER COMPOUND
  申请人：ZEON CORPORATION

  公开号：US20160052848A1

  公开（公告）日：2016-02-25

  The present invention is a method for producing a cycloalkyl alkyl ether compound comprising reacting substituted or unsubstituted cyclopentene or substituted or unsubstituted cyclohexene with an alcohol compound represented by a formula (2): R 1 OH (wherein R 1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms) in a gaseous state in presence of an acidic ion-exchange resin to produce a cycloalkyl alkyl ether compound represented by a formula (1): R 1 —O—R 2 (wherein R 1 is the same as defined above, and R 2 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group), the acidic ion-exchange resin having a specific surface area of 20 to 50 m 2 /g, an average pore size of 20 to 70 nm, and a total exchange capacity of 4.8 to 6.0 eq/L-R wet resin.

  本发明是一种生产环烷基烷基醚化合物的方法，包括将取代或未取代的环戊烯或取代或未取代的环己烯与公式（2）所表示的醇化合物反应：R1OH（其中R1是具有1至10个碳原子的取代或未取代的烷基或具有3至8个碳原子的取代或未取代的环烷基），在酸性离子交换树脂的存在下，在气态下生产环烷基烷基醚化合物，该化合物的化学式为（1）：R1—O—R2（其中R1与上述定义相同，R2是取代或未取代的环戊基或取代或未取代的环己基），酸性离子交换树脂具有20至50 m2/g的比表面积，20至70 nm的平均孔径和4.8至6.0 eq/L-R湿树脂的总交换容量。
• Mousseron et al., Bulletin de la Societe Chimique de France, 1948, p. 84,88
  作者：Mousseron et al.

  DOI：——

  日期：——
• Oxidation of organic sulphides. Part IV. Autoxidation of cyclohex-2-enyl methyl sulphide
  作者：L. Bateman、F. W. Shipley

  DOI：10.1039/jr9550001996

  日期：——
• Gritsenko, E. I.; Butenko, G. G.; Plemenkov, V. V., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 673 - 678
  作者：Gritsenko, E. I.、Butenko, G. G.、Plemenkov, V. V.

  DOI：——

  日期：——