3-(Phenylsulfonyl)cyclohex-2-en-1-ol | 65825-82-3

• 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-(Phenylsulfonyl)cyclohex-2-en-1-ol
• 英文别名: 3-(phenylsulfonyl)cyclohex-2-enol；3-(Benzenesulfonyl)cyclohex-2-en-1-ol
• CAS: 65825-82-3
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: PJLCSHWTZWBOBH-UHFFFAOYSA-N

物化性质

• 沸点：
  456.9±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(Phenylsulfonyl)cyclohex-2-en-1-ol 在 氢氧化钾 、 四丁基溴化铵 、 叔丁基锂 、 silica gel 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 3-benzylcyclohex-2-en-1-one
  参考文献：
  名称：

  Jin, Zhendong; Fuchs, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5995 - 5996

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(phenylsulfanyl)cyclohex-2-en-1-one 在 Oxone 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 3-(Phenylsulfonyl)cyclohex-2-en-1-ol
  参考文献：
  名称：

  Stereocontrolled cyclopentenone synthesis via cycloaddition

  摘要：

  DOI：

  10.1021/ja00201a032

文献信息

• Enzyme- and Ruthenium-Catalyzed Dynamic Kinetic Resolution of Functionalized Cyclic Allylic Alcohols
  作者：Richard Lihammar、Renaud Millet、Jan-E. Bäckvall

  DOI：10.1021/jo402086z

  日期：2013.12.6

  Enantioselective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been developed. Cyclopentadienylruthenium catalysts were used for the racemization, and lipase PS-IM or CALB was employed for the resolution. By optimization of the reaction conditions the formation of the enone byproduct was minimized, making it possible to prepare a range of optically active functionalized

  已经开发了通过动态动力学拆分的功能化环状烯丙基醇的对映选择性合成。环戊二烯基钌催化剂用于消旋，脂肪酶PS-IM或CALB用于拆分。通过优化反应条件，将烯酮副产物的形成减至最少，从而有可能以良好的收率和较高的ee值制备一系列光学活性的官能化烯丙基醇。
• Comparison of vinyl organolithium and organopalladium reagents for intramolecular conjugate addition to vinyl sulfones.
  作者：Sang Who Lee、P.L. Fuchs

  DOI：10.1016/s0040-4039(00)73954-2

  日期：1993.8

  Synthesis of cis-fused bicyclic ethers (5-10) by intramolecular conjugate addition of vinyl lithium and organopalladium reagents to cyclohexenyl/pentenyl moiety of vinyl sulfones is described.

  描述了通过将乙烯基锂和有机钯试剂分子内共轭加成到乙烯基砜的环己烯基/戊烯基部分上的顺式稠合双环醚（5-10）的合成。
• Regiospecific silver[I] promoted, palladium[O]-catalyzed intramolecular addition of aryl iodides to vinyl sulfones.
  作者：Zhendong Jin、P.L. Fuchs

  DOI：10.1016/s0040-4039(00)73953-0

  日期：1993.8

  Treatment of aryl iodides with 5% tetrakis(triphenylphosphine)palladium[O] in the presence of silver nitrate and triethylamine in acetonitrile at reflux effects intramotecular conjugate-addition/reductive elimination to generate an annulated vinyl sulfone. Omission of the silver nitrate produces mixtures of vinyl and allyl sulfones.

  在乙腈中，在硝酸银和三乙胺存在下，在硝酸银和三乙胺的存在下，用5％四（三苯基膦）钯[O]处理芳基碘化物，可实现分子内共轭加成/还原消除，从而生成环化的乙烯基砜。省略硝酸银会产生乙烯基和烯丙基砜的混合物。
• Intramolecular palladium-catalyzed cycloadditions with a cleavable tether
  作者：Barry M. Trost、Timothy A. Grese

  DOI：10.1021/ja00019a037

  日期：1991.9

  A facile synthesis of 2-(acyloxy)-3-methylene-4-(trimethylsilyl)butyric acids evolves from the use of tris(phenylthio)acetaldehyde as a practical glyoxylic ester equivalent. Introduction of the bifunctional donor of a [3 + 2] cycloaddition proceeds simply by esterification of an alcohol possessing TMM-PdL2 acceptor units. The synthetic flexibility of the sulfone leads to the choice of alpha, beta-unsaturated sulfones as the acceptors. Palladium-catalyzed cycloadditions proceed smoothly at temperatures as low as room temperature. Depending upon the substitution pattern and especially the conformation of the substrate, tethering the ester containing the bifunctional TMM unit at the carbon allylic to the acceptor provides substrates that predominantly to exclusively undergo cycloaddition rather than processes dominated by an alternative Pd(0)-catalyzed ionization. Since the ester linkage is easily cleaved, this sequence serves as a convenient strategy for controlled TMM-PdL2 cycloadditions. For example, the diastereofacial selectivity of this intramolecular process involves attack syn to the allylic oxygen in a six- or seven-membered-ring acceptor but anti to this oxygen in an intermolecular process. A diastereocontrolled cyclopentenone annulation is developed. Interestingly, the intramolecular cycloaddition of eight- and twelve-membered rings proceeds anti to the allylic oxygen. As an aside, the indefinite shelf life of the crystalline tris(phenylthio)acetaldehyde makes it a convenient glyoxylate synthon.
• Synthesis of carbazomycin B
  作者：Derrick L. J. Clive、Nola Etkin、Tomi Joseph、J. William Lown

  DOI：10.1021/jo00061a017

  日期：1993.4

  Carbazomycin B (1) was synthesized by radical cyclization of the sulfonamide 14 (Scheme III), followed by deprotection and dehydrogenation.