phenyl(undecyl)sulfane | 17763-59-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl(undecyl)sulfane
• 英文别名: (Undecylsulfanyl)benzene；undecylsulfanylbenzene
• CAS: 17763-59-6
• 化学式: C₁₇H₂₈S
• 分子量: 264.475
• InChiKey: GIDZOXHZBSNVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  phenyl(undecyl)sulfane 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以96%的产率得到十一烷
  参考文献：
  名称：

  硼化镍对苯并噻吩衍生物进行脱硫

  摘要：

  从六水合氯化镍和硼氢化钠就地方便地生成的硼化镍已被用于在异常温和的条件下将多种苯并噻吩衍生物脱硫为相应的烃。

  DOI：

  10.1039/c39900000819
• 作为产物：
  描述：

  辛烯 在 nickamine 、 异丙醇 、 sodium iodide 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 24.0h， 生成 phenyl(undecyl)sulfane
  参考文献：
  名称：

  镍钳复合物催化未活化烷基卤化物的Suzuki-Miyaura交叉偶联反应

  摘要：

  摘要 镍（II）钳形络合物[（Me N 2 N）Ni-Cl]用于催化未活化烷基卤化物的烷基-烷基和烷基-芳基的Suzuki-Miyaura偶联反应。9-烷基-9-硼环[3.3.1]壬烷和9-苯基-9-环环[3.3.1]壬烷试剂与卤代烷的偶联以中等至良好的收率实现。该反应可耐受各种有用的官能团，包括酯，醚，呋喃，硫醚，乙缩醛和Boc基团。 镍（II）钳形络合物[（Me N 2 N）Ni-Cl]用于催化未活化烷基卤化物的烷基-烷基和烷基-芳基的Suzuki-Miyaura偶联反应。9-烷基-9-硼环[3.3.1]壬烷和9-苯基-9-环环[3.3.1]壬烷试剂与卤代烷的偶联以中等至良好的收率实现。该反应可耐受各种有用的官能团，包括酯，醚，呋喃，硫醚，乙缩醛和Boc基团。

  DOI：

  10.1055/s-0033-1338544

文献信息

• Design, Synthesis and Antiplasmodial Evaluation of Sulfoximine-triazole Hybrids as Potential Antimalarial Prototypes
  作者：Tommy F. Mabasa、Babatunde Awe、Dustin Laming、Henok H. Kinfe

  DOI：10.2174/1573406415666190206232308

  日期：2019.8.26

  of new antimalarial agents, hybrids of triazoles and other known antimalarial drugs have been reported to possess better activity than either of the parent compounds administered individually. Despite their better activity, no hybrid antimalarial drugs have been developed so far. Objective: In the hope of developing new antimalarial prototypes, we propose the design, synthesis and antimalarial evaluation

  背景：由致命的恶性疟原虫菌株引起的疟疾每年夺去数百万人的生命。以青蒿素为基础的联合疗法（抗疟疾的最后一道防线）对恶性疟原虫耐药株的出现令人担忧，并敦促开发具有新作用方式的新型化学类型。在寻找新的抗疟药时，据报道，三唑与其他已知抗疟药的混合物比单独施用的母体化合物具有更好的活性。尽管它们具有更好的活性，但迄今为止尚未开发出混合抗疟药。 目的：希望开发新的抗疟原型，鉴于其有趣的生物学和生理特性，我们提出了新型亚砜亚胺-三唑杂种的设计，合成和抗疟评价。 方法：杂化物的亚砜亚胺部分将通过相应亚砜的酰亚胺化合成。设想了磺肟基亚胺的NH部分的丙基化，然后用苄基叠氮化物进行铜催化的点击化学，以提供目标磺胺基亚胺-三唑杂化物。 结果：成功合成了5个在亚砜亚胺基团上具有各种取代基的亚砜亚砜-三唑杂合体，并评估了它们的抗血浆和细胞毒性活性。结果表明，磺胺基亚胺和三唑基团与硫原子上的亲脂性烷基取代基并存会产生明显的活性。
• Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals
  作者：Dennis P. Curran、Amanda A. Martin-Esker、Sung Bo Ko、Martin Newcomb

  DOI：10.1021/jo00069a036

  日期：1993.8

  Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio) phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.
• Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies
  作者：Thomas G. Back、Denise L. Baron、Kexin Yang

  DOI：10.1021/jo00061a011

  日期：1993.4

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.
• Jones; Reid, Journal of the American Chemical Society, 1938, vol. 60, p. 2454
  作者：Jones、Reid

  DOI：——

  日期：——
• Takahashi,K. et al., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 757 - 762
  作者：Takahashi,K. et al.

  DOI：——

  日期：——