3-Phenylsulfonyl-hex-5-en-2-on | 71512-26-0

• 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-hex-5-en-2-on
• 英文别名: 5-Hexen-2-one, 3-(phenylsulfonyl)-；3-(benzenesulfonyl)hex-5-en-2-one
• CAS: 71512-26-0
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: PRVNDMHXICRDEF-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±45.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Phenylsulfonyl-hex-5-en-2-on 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以71%的产率得到5-iodomethyl-2-methyl-3-phenylsulfonyl-4,5-dihydrofuran
  参考文献：
  名称：

  乙酸锰合成螺环缩醛促进环外烯醇醚的加成

  摘要：

  β-酮酸酯和β-二羰基化合物与乙酸锰在乙酸中的反应生成中间体，将其加至环外烯醇醚中可制得各种有趣的螺环缩醛。由于显示出环外烯醇醚易于获得，因此该结果构成了基于自由基化学方法合成不饱和螺缩醛的有用途径。

  DOI：

  10.1016/s0040-4020(01)87231-8
• 作为产物：
  描述：

  1-(phenylsulfinyl)propan-2-one 在 bis(η3-allyl-μ-chloropalladium(II)) chromium(VI) oxide 、 氢氧化钾 、 高碘酸 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.25h， 生成 3-Phenylsulfonyl-hex-5-en-2-on
  参考文献：
  名称：

  在双相条件下钯催化的 α-亚磺酰基碳负离子的烯丙基烷基化

  摘要：

  钯催化的 α-亚磺酰基碳负离子的烯丙基烷基化可以在双相条件下发生。这些新条件为烯丙基化亚砜的高产率提供了一种简单、温和且有效的途径。该反应容许多种 EWG 基团作为额外的碳负离子稳定基团，例如酯、乙酰基、氰基、酰胺、磺酰基和亚磺酰基官能团。

  DOI：

  10.1055/s-2006-939702

文献信息

• Alkylation and Acylation of Active Methylene Compounds Using 1,8-Diazabicyclo[5.4.0]undec-7-ene as a Base
  作者：Noboru Ono、Tetsuji Yoshimura、Tadashi Saito、Rui Tamura、Rikuhei Tanikaga、Aritsune Kaji

  DOI：10.1246/bcsj.52.1716

  日期：1979.6

  Active methylene compounds are selectively monoalkylated with alkyl halides in benzene using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a base. Selectivity of monoalkylation decreases when the reaction is carried out in a polar solvent. Ethyl acetoacetate is O-acylated with acyl halides in the presence of DBU in acetonitrile to give the (E)-enol esters stereoselectively.

  使用 1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU) 作为碱，在苯中用烷基卤选择性单烷基化活性亚甲基化合物。当反应在极性溶剂中进行时，单烷基化的选择性降低。在乙腈中存在 DBU 的情况下，乙酰乙酸乙酯用酰卤 O-酰化，立体选择性地得到 (E)-烯醇酯。
• Chemistry of baker's yeast reduction products: Use of optically active (S)-(+)-1-(p-toluenesulfonyl)propan-2-ol and (S)-(+)-1-(phenylsulfonyl)propan-2-ol in synthesis.
  作者：Alan P. Kozikowski、B.B. Mugrage、C.S. Li、L. Felder

  DOI：10.1016/s0040-4039(00)85071-6

  日期：1986.1

  The utility of the title compounds in the preparation of optically active lactones and alcohols is detailed.

  详细说明了标题化合物在制备光学活性内酯和醇中的用途。
• pH optimization of nucleophilic reactions in water
  作者：J. F. King、R. Rathore、J. Y. L. Lam、Z. R. Guo、D. F. Klassen

  DOI：10.1021/ja00034a040

  日期：1992.4

  We present a way of prescribing the pH for a reaction so as to obtain either (a) maximum yield in competition with hydrolysis or (b) selective reaction at either of two sites in such nucleophile-electrophile reactions as C-alkylation of acidic ketones and the acylation and sulfonylation of amines. First, we derive the following general equation for pH(max), the pH giving the highest yield of the product (P) of the reaction of a nucleophile (Nu) with a hydrolyzable electrophile (E) in water: pH(max) = 1/2[log (k(w)/k(OH)) + pK(w) + pK(a)] (k(w) and k(OH) refer to the water- and hydroxide-promoted hydrolyses of E, K(w) is the autoprotolysis constant of water, and K(a) is the acid dissociation constant of NuH+, the conjugate acid of Nu). pH(max) thus depends on a property of E (namely, k(w)/k(OH)) and a property of Nu (the pK(a) of NuH+), but not on the rate constant for the reaction of E with Nu or the concentration of Nu. We then deduce analogous approximate equations for maximum selectivity for reaction at either of two nucleophilic sites, specifically, equations giving pH(xmax) and pH(ymax), the pH values for the maximum yields of the respective products (P(x) and P(y)) of the reactions of E with the two nucleophiles. We find that (a) pH-yield profiles calculated from the equations concur with observed yields for reactions under pseudo-first-order conditions and (b) preparative experiments at the estimated pH values give good to excellent yields of clean products and high selectivity in both the C-alkylation and Schotten-Baumann reactions.
• Efficient Diastereoselective Syntheses of <i>erythro</i>- or <i>threo</i>-α-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCl₄/BH₃ or LiEt₃BH/CeCl₃, Respectively
  作者：Enrico Marcantoni、Simone Cingolani、Giuseppe Bartoli,*、Marcella Bosco、Letizia Sambri

  DOI：10.1021/jo972284k

  日期：1998.5.1

  A stereoselective synthesis of erythro- and threo-alpha-alkyl-beta-hydroxy sulfones by reduction of the corresponding alpha-alkyl-beta-keto sulfones has I,een developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 degrees C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the three isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of alpha-allyl-beta-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.
• Lee, Joe Wook; Oh, Dong Young, Heterocycles, 1990, vol. 31, # 8, p. 1417 - 1421
  作者：Lee, Joe Wook、Oh, Dong Young

  DOI：——

  日期：——