2-(4-(prop-2-ynyloxy)phenyl)-4,5-dihydro-1,3-dithiole | 143334-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-(prop-2-ynyloxy)phenyl)-4,5-dihydro-1,3-dithiole
• 英文别名: 2-{4-[(Prop-2-yn-1-yl)oxy]phenyl}-1,3-dithiolane；2-(4-prop-2-ynoxyphenyl)-1,3-dithiolane
• CAS: 143334-73-0
• 化学式: C₁₂H₁₂OS₂
• mdl: MFCD28009951
• 分子量: 236.359
• InChiKey: NVXFYCAIQRYBIO-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±42.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  癸硼烷 、 2-(4-(prop-2-ynyloxy)phenyl)-4,5-dihydro-1,3-dithiole 在 acetonitrile 作用下， 以 乙腈 为溶剂， 以51%的产率得到1-{4-(4,5-dihydro-1,3-dithiol-2-yl)phenoxymethyl}-1,2-dicarba-closo-dodecaborane(12)
  参考文献：
  名称：

  Tumour-targetted boranes. Part 2. Coupling of closo-carboranes to substituted 2-nitroimidazoles via 1,3-dipolar cycloaddition

  摘要：

  Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer. Direct syntheses of carboranes linked to 2-nitroimidazole were unsuccessful. A mild procedure for 1,3-dipolar cycloaddition of 4-(carboranylmethoxy)benzonitrile N-oxide 32 with a nitroimidazolyl-alkene 27 and with nitroimidazolyl-alkynes 3 and 30 has been developed. using a series of model reactions, yielding a dihydroisoxazole 28 and the isoxazoles 29 and31. respectively. The nitrile oxide 32 is unusually stable. Dithioacetals are shown to be suitable protecting groups for aromatic aldehydes under the vigorous reductive and Lewis acidic-basic conditions,of carborane formation. 6-Methoxy-4H-[1]benzopyrano[4,3-c]isoxazole 16 been synthesised by intramolecular 1,3-dipolar cycloaddition. The structure of-the isoxazole derivative 29 has been confirmed by an X-ray crystal structure analysis.

  DOI：

  10.1039/p19940000203
• 作为产物：
  描述：

  4-(丙-2-炔-1-基氧基)苯甲醛 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-(prop-2-ynyloxy)phenyl)-4,5-dihydro-1,3-dithiole
  参考文献：
  名称：

  DNA Binding Compounds. VII. Synthesis, Characterization and DNA Binding Capacity of 1,2-Dicarba-closo-dodecaborane Bibenzimidazoles Related to the DNA Minor Groove Binder Hoechst 33258

  摘要：

  以已知的 DNA 小沟粘合剂 Hoechst 33258 为基础，制备了一系列联苯并咪唑衍生物。 粘合剂 Hoechst 33258 的基础上制备了一系列联苯并咪唑衍生物，其中包括一个 1,2-dicarba-closo-dodecaborane 笼，可用于 硼中子俘获疗法（BNCT）。选择硼烷衍生物 (5){(7) 的选择是为了减少之前制备的硼烷衍生物（5）{（7）对小沟 DNA 结合的立体抑制作用。 的立体抑制作用。这些双硼烷衍生物的合成和 DNA 结合的初步研究。 在此介绍。

  DOI：

  10.1071/c98148

文献信息

• Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapyElectronic supplementary information (ESI) available: experimental details for the synthesis of compounds 12–15, 31 and 32. See http://www.rsc.org/suppdata/ob/b2/b209534c/
  作者：Christophe Frixa、Mary F. Mahon、Andrew S. Thompson、Michael D. Threadgill

  DOI：10.1039/b209534c

  日期：2003.1.13

  Selective delivery of 10B to tumours is one of the major remaining problems in boron neutron capture therapy (BNCT) of cancer. Porphyrins are selectively accumulated in tumours. Thus two series of carborane-carrying porphyrins were constructed, with additional functionality for attachment of uncharged potentially water-solubilising polyethers. 3-(1,2-Dicarbaclosododecaboran(12)-1-ylmethoxy)benzaldehyde

  选择性向肿瘤中递送10B是癌症的硼中子俘获疗法（BNCT）中主要的主要问题之一。卟啉选择性地积累在肿瘤中。因此，构建了两个系列的携带碳硼烷的卟啉，并具有附加功能，用于连接不带电荷的潜在水溶性聚醚。通过保护3-（丙-2-炔氧基）苯甲醛作为二硫缩醛的醛，用十硼烷（14）处理并脱保护，制得3-（1,2-二咔唑/十二碳硼烷（12）-1-基甲氧基）苯甲醛。与3-硝基苯基二吡咯甲烷的缩合得到中-（3-硝基苯基）-间-（3-碳戊基甲氧基苯基）卟啉的可分离混合物，这是由于在卟啉原阶段的大量加扰而产生的。同样，3-（1，将2-二咔唑基十二碳硼烷（12）-1-基）苯甲醛与该二吡咯甲烷制得类似的内消旋-（3-硝基苯基）-内消旋-（3-羰基苯基）卟啉混合物。在第二个系列中，两个区域异构的双（硝基苯基）双（碳烷基苯基）卟啉只能通过X射线晶体学来区分，它们的NMR谱图是相同的。用氯化锡（II）将单（硝基苯基）卟啉和双
• Synthesis of carborane-containing nitroimidazole compounds via mild 1,3-dipolar cycloadition
  作者：Martin Scobie、Michael D. Threadgill

  DOI：10.1039/c39920000939

  日期：——

  Nitroimidazole-linked carboranes are synthesised in good yield from ω-alkenyl- and ω-alkynyl-2-nitroimidazoles and a carborane nitrile oxide by 1,3-dipolar cycloaddition under mild conditions.

  经过温和条件下的1,3-双极环加成反应，ω-烯基和ω-炔基-2-硝基咪唑与碳硼烷脂腈氧化物合成了氮杂咪唑连接的碳硼烷，产率良好。
• Tumour-targetted boranes. Part 2. Coupling of closo-carboranes to substituted 2-nitroimidazoles via 1,3-dipolar cycloaddition
  作者：Martin Scobie、Mary F. Mahon、Michael D. Threadgill

  DOI：10.1039/p19940000203

  日期：——

  Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer. Direct syntheses of carboranes linked to 2-nitroimidazole were unsuccessful. A mild procedure for 1,3-dipolar cycloaddition of 4-(carboranylmethoxy)benzonitrile N-oxide 32 with a nitroimidazolyl-alkene 27 and with nitroimidazolyl-alkynes 3 and 30 has been developed. using a series of model reactions, yielding a dihydroisoxazole 28 and the isoxazoles 29 and31. respectively. The nitrile oxide 32 is unusually stable. Dithioacetals are shown to be suitable protecting groups for aromatic aldehydes under the vigorous reductive and Lewis acidic-basic conditions,of carborane formation. 6-Methoxy-4H-[1]benzopyrano[4,3-c]isoxazole 16 been synthesised by intramolecular 1,3-dipolar cycloaddition. The structure of-the isoxazole derivative 29 has been confirmed by an X-ray crystal structure analysis.
• DNA Binding Compounds. VII. Synthesis, Characterization and DNA Binding Capacity of 1,2-Dicarba-closo-dodecaborane Bibenzimidazoles Related to the DNA Minor Groove Binder Hoechst 33258
  作者：Stuart A. Bateman、David P. Kelly、Jonathan M. White、Roger F. Martin

  DOI：10.1071/c98148

  日期：——

  A series of bibenzimidazole derivatives based on the known DNA minor groove binder Hoechst 33258 have been prepared to include a 1,2-dicarba-closo-dodecaborane cage for potential use in boron neutron capture therapy (BNCT). The carborane derivatives (5)(7) were chosen to reduce the steric inhibition of minor groove DNA binding displayed by the previously prepared carborane ligand (4). The synthesis and preliminary DNA binding studies of these bibenzimidazole derivatives are presented herein.

  以已知的 DNA 小沟粘合剂 Hoechst 33258 为基础，制备了一系列联苯并咪唑衍生物。 粘合剂 Hoechst 33258 的基础上制备了一系列联苯并咪唑衍生物，其中包括一个 1,2-dicarba-closo-dodecaborane 笼，可用于 硼中子俘获疗法（BNCT）。选择硼烷衍生物 (5)(7) 的选择是为了减少之前制备的硼烷衍生物（5）（7）对小沟 DNA 结合的立体抑制作用。 的立体抑制作用。这些双硼烷衍生物的合成和 DNA 结合的初步研究。 在此介绍。