dec-1-yn-1-yl(trifluoromethyl)sulfane | 1403612-50-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: dec-1-yn-1-yl(trifluoromethyl)sulfane
• 英文别名: 1-(Trifluoromethylsulfanyl)dec-1-yne；1-(trifluoromethylsulfanyl)dec-1-yne
• CAS: 1403612-50-9
• 化学式: C₁₁H₁₇F₃S
• 分子量: 238.317
• InChiKey: BVJCBYFWPOIPLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-癸炔 、 1-trifluoromethylthio-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole 在 2,2'-联吡啶 、 溴化亚铜二甲硫醚 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 以61%的产率得到dec-1-yn-1-yl(trifluoromethyl)sulfane
  参考文献：
  名称：

  三氟甲基硫醇化的亲电高价碘试剂

  摘要：

  硫磺和朋友：已开发出一种新的亲电子高价碘试剂1用于直接三氟甲基硫醇化。各种亲核试剂（包括β-酮酸酯，醛，酰胺，芳基或乙烯基硼酸和炔烃）在温和的条件下与1反应，以良好的产率获得了相应的三氟甲基硫代化合物。

  DOI：

  10.1002/anie.201209817

文献信息

• Base-Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes
  作者：Sébastien Alazet、Luc Zimmer、Thierry Billard

  DOI：10.1002/anie.201305179

  日期：2013.10.4

  Pin the tail on the alkyne: CF3S‐ or CF3CF2S‐alkynes can be simply and quickly obtained by mixing terminal alkynes with a trifluoromethanesulfenamide reagent. The reaction uses easy‐to‐handle reagents, and functions under mild conditions without activation by transition metals.

  将尾巴钉在炔烃上：通过将末端炔烃与三氟甲亚磺酰胺试剂混合，可以轻松快速地获得CF 3 S-或CF 3 CF 2 S-炔烃。该反应使用易于处理的试剂，可在温和条件下运行，而不会被过渡金属激活。
• Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides
  作者：François Baert、Julie Colomb、Thierry Billard

  DOI：10.1002/anie.201205156

  日期：2012.10.8

  It's so easy! Direct trifluoromethanesulfanylation reactions remain difficult to perform because of the lack of reagents that are stable and easy to handle. Trifluoromethanesulfanamides are reagents which, in combination with readily available Grignard reagents, can be used by those without experience in fluorine chemistry to easily synthesize trifluoromethylthioethers.

  它是如此容易！由于缺乏稳定且易于处理的试剂，直接三氟甲烷磺酰化反应仍然难以进行。三氟甲硫酰胺是与容易获得的格利雅试剂结合使用的试剂，对于那些没有氟化学经验的人来说，可以很容易地合成三氟甲基硫醚。
• Expeditious trifluoromethylthiolation and trifluoromethylselenolation of alkynyl(phenyl)iodoniums by [XCF₃]⁻ (X = S, Se) anions
  作者：Wan-Yin Fang、Tao Dong、Jia-Bin Han、Gao-Feng Zha、Cheng-Pan Zhang

  DOI：10.1039/c6ob02107g

  日期：——

  on and trifluoromethylselenolation of alkynyl(phenyl)iodonium tosylates by [XCF3]− (X = S, Se) ions was accomplished in 5–10 minutes at room temperature under a N2 atmosphere and provided a variety of alkynyl trifluoromethyl sulfides and selenides in good yields. Compared to the known methods, this approach has several advantages such as short reaction times and metal- and additive-free conditions

  [XCF 3 ] -（X = S，Se）离子在室温下于N 2气氛下于5-10分钟内完成对甲苯磺酸炔基（苯基）碘化物的三氟甲基硫醇化和三氟甲基硒化反应，并在室温下提供了各种炔基三氟甲基硫化物和硒化物良品率高。与已知方法相比，该方法具有多个优点，例如反应时间短，无金属和无添加剂的条件，而无需使用过量的[Me 4 N] [XCF 3 ]试剂。此外，（苯基乙炔基）苯并恶唑醇（on）e与[Me 4 N] [XCF 3]在标准条件下的结果表明，无环炔基（苯基）碘鎓在转化中是更强大的炔基来源。该协议允许快速方便地访问大量炔基三氟甲基硫化物和硒化物。
• Photocatalyzed Cascade Hydrogen Atom Transfers for Assembly of Multi‐Substituted α‐SCF3 and α‐SCF2H Cyclopentanones
  作者：Nicolas Marie、Jun‐An Ma、Vincent Tognetti、Dominique Cahard

  DOI：10.1002/anie.202407689

  日期：2024.8.19

  A photocatalyzed formal (3+2) cycloaddition has been developed to construct original polysubstituted α‐SCF3 cyclopentanones in a regio‐ and diastereoselective manner. This building block approach leverages trifluoromethylthio alkynes and branched / linear aldehydes, as readily available reaction partners, in consecutive hydrogen atom transfers and C–C bond formations. Difluoromethylthio alkynes are also compatible subtrates. Furthermore, the potential for telescoped reaction starting from alcohols instead of aldehydes was demonstrated, as well as process automatization and scale‐up under continuous microflow conditions. This prompted density functional theory calculations to support a free radical‐mediated cascade hydrogen atom transfer process.