3,3-Dimethyl-1-butynylphenyl sulfone | 134418-65-8

• 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: 3,3-Dimethyl-1-butynylphenyl sulfone
• 英文别名: <(3,3-Dimethyl-1-butynyl)sulfonyl>benzene；tert-butylethynyl phenyl sulfone；3,3-Dimethylbut-1-ynylsulfonylbenzene
• CAS: 134418-65-8
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: ZQCSVYXKABEQNL-UHFFFAOYSA-N

物化性质

• 沸点：
  332.6±25.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3,3-Dimethyl-1-butynylphenyl sulfone 、 1-(二乙氨基)丙炔 生成 (2-Benzenesulfonyl-3-tert-butyl-4-methyl-cyclobutadienyl)-diethyl-amine
  参考文献：
  名称：

  Sulfone reagents in organic synthesis. 8. Cyclobutadiene intermediates in cycloaddition reactions of 1-alkynyl sulfones with 1-alkynylamines

  摘要：

  The initially formed product from ynamines, such as diethyl(1-propynl)amine, and 1-alkynyl sulfones is in fact the corresponding cyclobutadiene and not the 2-sulfinyl-4-aminofuran proposed by Himbert. The formation of the cyclobutadiene ring has been established by MS, IR, and H-1 NMR data, as well as by chemical trapping experiments.

  DOI：

  10.1021/jo00013a005
• 作为产物：
  描述：

  2-Phenylsulfanyl-1-tert-butylethyne 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3,3-Dimethyl-1-butynylphenyl sulfone
  参考文献：
  名称：

  使用催化 FeII 和维生素 C 进行脱烯基烷基化

  摘要：

  在本文中，我们报道了在炔基砜存在下，通过臭氧介导和 Fe II催化的未活化烯烃的脱烯基炔基化合成烷基链炔烃。这种一锅反应采用催化 Fe II盐和L-抗坏血酸的组合，在温和的条件下进行，具有良好的效率、高立体选择性和广泛的官能团兼容性。与我们之前的 Fe II介导的 α-甲氧基氢过氧化物还原断裂相比，Fe II催化的过程是通过对多个竞争自由基（氧化还原）途径进行彻底的动力学分析而设计的。我们强调了这种脱烯基炔基化通过复杂分子（包括天然产物和药物）的多次合成后转化和后期多样化的潜力。

  DOI：

  10.1021/jacs.2c05980

文献信息

• Direct synthesis of C3-alkynyl pyrroloindolines from tryptamines <i>via</i> a visible-light-induced radical cascade reaction
  作者：LinLin Ren、Yonggong Wang、Yanman Huo、Xiaogang Tong、Chengfeng Xia

  DOI：10.1039/d2cc05905c

  日期：——

  A visible-light-induced radical cascade reaction for the direct alkynylation of tryptamines with alkynyl sulfones was developed, affording a series of C3-alkynyl pyrroloindolines in excellent yields. This method features readily available substrates, good functional group tolerability, and scalability. C3-alkynyl pyrroloindolines show great potential as useful building blocks in the preparation of

  开发了一种可见光诱导的自由基级联反应，用于色胺与炔基砜的直接炔基化，以优异的收率提供了一系列 C3-炔基吡咯并二氢吲哚。该方法具有现成的底物、良好的官能团耐受性和可扩展性。C3-炔基吡咯并二氢吲哚在制备复杂且有价值的吡咯并二氢吲哚生物碱方面显示出作为有用结构单元的巨大潜力。
• Nucleophilic vinylic substitutions of (Z)-(β-(phenylsulfonyl)-alkenyl)iodonium tetrafluoroborates with tetrabutyl-ammonium halides: retention of configuration
  作者：Masahito Ochiai、Kunio Oshima、Yukio Masaki

  DOI：10.1016/0040-4039(91)80572-n

  日期：1991.12

  Nucleophilic vinylic substitutions of (Z)-(β-(phenylsulfonyl)alkenyl)-phenyliodonium tetrafluoroborates 1 with tetrabutylammonium halides (Cl, Br, and I) proceed with exclusive retention of configuration at room temperature and afford (Z)-β-(phenylsulfonyl)vinyl halides 2 in high yields.

  （Z）-（β-（苯磺酰基）烯基）-苯基碘鎓氟四氟硼酸酯1的亲核乙烯基取代被卤化四丁基铵（Cl，Br和I）继续在室温下保留构型，得到（Z）-β-（苯磺酰基）卤代乙烯2的收率很高。
• Steric Effects on the Regioselectivity of an Azide-Alkyne Dipolar Cycloaddition Reaction: The Synthesis of Human Leukocyte Elastase Inhibitors
  作者：Dennis J. Hlasta、James H. Ackerman

  DOI：10.1021/jo00100a019

  日期：1994.10

  The cycloaddition reaction of N-(azidomethyl)benzisothiazolone 4 with various electron-deficient acetylenes gave a novel series of 1,2,3-triazoles 5-15 that were prepared for testing as inhibitors of human leukocyte elastase (HLE). Steric effects controlled the reaction regioselectivity, since as the acetylene substituent size increased from hydrogen to phenyl, tert-butyl, and trimethylsilyl, the regioisomer ratios reversed. An electronic effect of silicon appears to be responsible for the formation of only one isomer with the trimethylsilyl acetylenecarboxylate and ethynyl sulfone. For example, the 5-(phenylsulfonyl)triazole 13b was the only regioisomer detected in the reaction of phenyl 2-(trimethylsilyl)ethynyl sulfone with the azide 4. The strongly electron-withdrawing sulfone exerted no control over the regioselectivity of the cycloaddition reaction in comparison to the dominating effect of the trimethylsilyl group. High pressure and water as solvent were separately shown to accelerate the rate of product formation. The structures were unambiguously assigned on the basis of an X-ray crystal structure determination and NOE difference experiments. The derivative 12a, WIN 68123, is a potent HLE inhibitor with an apparent binding constant (K-i*) of 0.38 nM.
• Hypervalent Iodine in Synthesis: 9. A New, Effective Synthesis of Acetylenic Sulfones
  作者：Zu-Dong Liu、Zhen-Chu Chen

  DOI：10.1080/00397919208021333

  日期：1992.7

  Alkynylphenyliodonium salts can easily react with sodium sulfinates under PTC conditions at room temperature to afford a convenient, effective method for the preparation of acetylenic sulfones.
• EISCH, JOHN J.;HALLENBECK, LAWRENCE E.;LUCARELLI, MICHAEL A., J. ORG. CHEM., 56,(1991) N3, C. 4095-4096
  作者：EISCH, JOHN J.、HALLENBECK, LAWRENCE E.、LUCARELLI, MICHAEL A.

  DOI：——

  日期：——