1-bromo-3,4,5-tridodecylsulfanylbenzene | 1372535-62-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-bromo-3,4,5-tridodecylsulfanylbenzene
• 英文别名: 3,4,5-tri(dodecylsulfanyl)bromobenzene
• CAS: 1372535-62-0
• 化学式: C₄₂H₇₇BrS₃
• 分子量: 758.175
• InChiKey: CTNXMSHTHSFDLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.49
• 重原子数：
  46.0
• 可旋转键数：
  36.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-bromo-3,4,5-tridodecylsulfanylbenzene 在 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  追逐硫醚取代的黄鎓盐在溶液和散装状态下的自组装

  摘要：

  硫磺稳定！硫越多，在黄素 ILC 中稳定的柱状相越好。在溶液中，特别是在 B 环上的硫醚对吸收光谱产生助色效应并导致反平行柱状堆积。

  DOI：

  10.1002/cphc.202200154
• 作为产物：
  描述：

  3,4,5-三氟溴苯 、 十二硫醇 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 10.0h， 以82%的产率得到1-bromo-3,4,5-tridodecylsulfanylbenzene
  参考文献：
  名称：

  追逐硫醚取代的黄鎓盐在溶液和散装状态下的自组装

  摘要：

  硫磺稳定！硫越多，在黄素 ILC 中稳定的柱状相越好。在溶液中，特别是在 B 环上的硫醚对吸收光谱产生助色效应并导致反平行柱状堆积。

  DOI：

  10.1002/cphc.202200154

文献信息

• Synthesis of oleophilic electron-rich phenylhydrazines
  作者：Aleksandra Jankowiak、Piotr Kaszyński

  DOI：10.3762/bjoc.8.29

  日期：——

  Phenylhydrazines 1 substituted with two or three long-chain alkyl, alkoxy or alkylsulfanyl groups were successfully prepared by acid-induced removal of the Boc group in hydrazides 2. The reaction is carried out with 5 equivalents of TfOH in CF₃CH₂OH/CH₂Cl₂ at −40 °C for 1.5 min. Under these conditions, the deprotected hydrazine 1 is fully protonated, which increases its stability in the reaction medium. The hydrazines were isolated in 60–86% yields and purities >90%. The hydrazides 2 were obtained in 43–71% yields from aryl bromides 5, which were lithiated with t-BuLi and subsequently reacted with di-tert-butyl azodicarboxylate (DTBAD).

  苯基肼1通过酸诱导去除肼酰胺2中的Boc基团，成功地取代了两个或三个长链烷基、烷氧基或烷基硫基团。反应在CF₃CH₂OH/CH₂Cl_{2>中以5当量的TfOH在-40°C下进行1.5分钟。在这些条件下，去保护的肼1被完全质子化，增加了其在反应介质中的稳定性。肼类产物以60-86%的产率和纯度>90%的纯度分离。肼酰胺2以43-71%的产率从芳基溴化物5中获得，该溴化物通过与t-BuLi锂化，然后与双tert-丁基叠氮二羧酸酯（DTBAD）反应得到。}
• Substituent-Dependent Magnetic Behavior of Discotic Benzo[<i>e</i>][1,2,4]triazinyls
  作者：Marcin Jasiński、Jacek Szczytko、Damian Pociecha、Hirosato Monobe、Piotr Kaszyński

  DOI：10.1021/jacs.6b06444

  日期：2016.8.3

  Discotic mesogens containing the benzo[e][1,2,4]triazinyl radical as the central unit exhibit a Col(h) phase below 80 degrees C. Depending on the substituent at the N(1) position, they show different modes of thermal expansion and magnetic behavior, presumably due to differences in molecular organization. Thus, for 1-phenyl (1a) and 1-PhF-m (1b) derivatives, the Col(h) phase has positive thermal expansion coefficient kappa and antiferromagnetic interactions, while for the 1-(3,4,5-(C12H25X)(3)C6H2) derivatives 1c (X = O) and 1d (X = S), kappa is negative and weak ferromagnetic interactions in the crystalline phase are observed for 1c (j/k(B) = +4.76 K). Compounds 1a and 1c exhibit photoinduced hole transport (mu approximate to 1.3 X 10(-3) cm(2) V-1 s(-1)) in the Col(h) phase.
• Synthesis of 3,4-dialkylsulfanyl- and 3,4,5-trialkylsulfanyl derivatives of bromobenzene and benzaldehyde
  作者：Aleksandra Jankowiak、Żaneta Debska、Jarosław Romański、Piotr Kaszyński

  DOI：10.1080/17415993.2011.644554

  日期：2012.2.1

  3,4-Dialkylsulfanyl- (1a[n], n = 8, 9, 11) and 3,4,5-trialkylsulfanylbromobenzenes (1b[n], n = 6, 8, 10, 12) were prepared from 3,4-difluoro- and 3,4,5-trifluorobromobenzene, respectively, in 50-60% yields. The bromobenzenes 1[n] were converted to benzaldehydes 2[n] by lithium-halogen exchange followed by reaction with DMF.[GRAPHICS].
• Induction of Columnar Discotic Behavior in Verdazyl Radicals with Alkylsulfanyl Substituents
  作者：Aleksandra Jankowiak、Damian Pociecha、Hirosato Monobe、Jacek Szczytko、Żaneta Dębska、Jarosław Romański、Piotr Kaszyński

  DOI：10.1080/10426507.2012.736896

  日期：2013.4.1

  Substitution of the 1,3,5-triphenyl-6-oxoverdazyl radical with n-alkylsulfanyl groups lead to derivatives 1[n], which exhibit a columnar rectangular phase (Col(r) ) below 60 degrees C. Compounds 1[n] have a broad absorption band in the visible region with maxima at 540 and 610nm and redox potentials E0/+1 (1/2) = +0.99V and E0/-1 (1/2) = -0.45V vs. SCE. Time-of-flight (TOF) investigation of 1[8] revealed hole mobility of (h) = 1.52 x 10(-3) cm(2) V-1 s(-1) in the columnar phase with an activation energy E-a = 0.06 +/- 0.01eV. Magnetization studies of 1[8] demonstrated nearly ideal paramagnetic behavior in both solid and fluid phases above 200K and weak antiferromagnetic interactions at low temperatures. Verdazyl derivatives 1[n] were prepared in a sequence of reactions starting from 1-bromo-3,4,5-trifluorobenzene by alkylsulfanylation, followed by hydrazinylation, and finally 6-oxoverdazyl ring assembly using the Milcent method.