4-ethynyl-N,N-[1,2-bis(dimethylsilyl)ethano]aniline | 312745-65-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-ethynyl-N,N-[1,2-bis(dimethylsilyl)ethano]aniline
• 英文别名: 1-(4-ethynylphenyl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine
• CAS: 312745-65-6
• 化学式: C₁₄H₂₁NSi₂
• 分子量: 259.498
• InChiKey: IGIZXTWKYHCABX-UHFFFAOYSA-N

物化性质

• 沸点：
  300.1±44.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-ethynyl-N,N-[1,2-bis(dimethylsilyl)ethano]aniline 在 sodium sulfide 、 sodium tetrahydroborate 、 正丁基锂 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.5h， 生成 2,6-bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium hexafluorophosphate
  参考文献：
  名称：

  In Vitro Photodynamic Properties of Chalcogenopyrylium Analogues of the Thiopyrylium Antitumor Agent AA1

  摘要：

  Several series of chalcogenopyrylium dyes were prepared with one or two 4-anilino substituents at the 2- and 6-positions and with phenyl, 4-N,N-dimethylanilino, or 4-(N-morphilino)phenyl substituents at 2- and/or 4-positions. The dye series are all related in structure to AA1, a thiopyrylium dye that targets mitochondria. The chalcogenopyrylium. nuclei included sulfur, selenium, and tellurium at the 1-position. Key intermediates in the dye synthesis were the corresponding Delta-4H-chalcogenopyran-4-ones. All of the dyes of this study were evaluated for dark and phototoxicity toward Colo-26 cells in vitro. There was no correlation of dark toxicity with either the reduction potential of the chalcogenopyrylium dye or the n-octanol/water partition coefficient, log P. Several of the dyes of this study (thiopyrylium dyes 1-S and 13-S, selenopyrylium dyes 1-Se, 2-Se, 3-Se, 4-Se, 13-Se, 14-Se, and 27-Se, and telluropyrylium dye 13-Te) showed added phototoxicity upon irradiation. Dyes with the highest therapeutic ratio as measured by dark toxicity/phototoxicity (15 J cm(-2) of 360-800-nm light) had values of log P of 1.0-1.2. Studies of cytochrome c oxidase activity in whole R3230AC cells suggested that dyes I-S and 3-Se, with values of log P of 2.2 and 1.7, respectively, were localized in the mitochondria. Cytocrome c oxidase activity in whole cells was inhibited by 1-S and 3-Se in the dark. Chalcogenopyrylium dyes 2-Se, 4-Se, 13-Te, and 14-Se inhibited whole-cell cytochrome c oxidase activity only following irradiation, which suggests that these dyes relocalized to mitochondria following irradiation.

  DOI：

  10.1021/jm020260m
• 作为产物：
  描述：

  4-(4-aminophenyl)-2-methyl-3-butyn-2-ol trifluoroacetamide 在 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 6.0h， 生成 4-ethynyl-N,N-[1,2-bis(dimethylsilyl)ethano]aniline
  参考文献：
  名称：

  A Selenopyrylium Photosensitizer for Photodynamic Therapy Related in Structure to the Antitumor Agent AA1 with Potent in Vivo Activity and No Long-Term Skin Photosensitization

  摘要：

  Cationic chalcogenopyrylium dyes 5 were synthesized in six steps from p-aminophenylacetylene (9), have absorption maxima in methanol of 623, 654, and 680 nm for thio-, seleno-, and telluropyrylium dyes, respectively, and generate singlet oxygen with quantum yields [Phi(O-1(2))] of 0.013, 0.029, and 0.030, respectively. Selenopyrylium dye 5-Se was phototoxic to cultured murine Colo-26 and Molt-4 cells. Initial acute toxicity studies in vivo demonstrate that, at 29 mg (62 mu mol)/kg, no toxicity was observed with 5-Se in animals followed for 90 days under normal vivarium conditions. In animals given 10 mg/kg of 5-Se via intravenous injection, 2-8 nmol of 5-Se/g of tumor was found at 3, 6, and 24 h postinjection. Animals bearing R3230AC rat mammary adenocarcinomas were treated with 10 mg/kg of 5-Se via tail-vein injection and with 720 J cm(-2) of 570-750-nm light from a filtered tungsten lamp at 200 mW cm(-2) (24 h postinjection of 5-Se). Treated animals gave a tumor-doubling time of 9 +/- 4 days, which is a 300% increase in tumor-doubling time relative to the; 3 +/- 2 days for untreated dark controls. Mechanistically, the mitochondria appear to be a target. In cultured R3230AC rat mammary adenocarcinoma cells treated with 0.1 and 1.0 muM 5-Se and light, mitochondrial cytochrome c oxidase activity was inhibited relative to cytochrome c oxidase activity in untreated cells. Irradiation of isolated mitochondrial suspensions treated with 10 muM dye 5-Se inhibited cytochrome c oxidase activity. The degree of enzyme inhibition was abated in a reduced oxygen environment. Superoxide dismutase, at a final concentration of 30 U, did not alter the photosensitized inhibition of mitochondrial cytochrome c oxidase by dye 5-Se. The data suggest that singlet oxygen may play a major role in the photosensitized inhibition of mitochondrial cytochrome c oxidase.

  DOI：

  10.1021/jm000154p

文献信息

• Synthesis and Properties of Dithiocarbamate-Linked Acenes
  作者：Jingjing Zhang、Nicholas R. Myllenbeck、Trisha L. Andrew

  DOI：10.1021/acs.orglett.6b03492

  日期：2017.1.6

  A small set of unsymmetrically substituted acene derivatives containing either aniline or dithiocarbamate moieties was synthesized. A stepwise, one-pot procedure was used to transform appropriate acenequinones to aniline-linked acenes in one step with moderate yields. A heretofore-unreported carbon disulfide activation process involving the formation of a trialkylammonium dithiocarbamate intermediate

  合成了少量的不对称取代的含苯胺或二硫代氨基甲酸酯部分的并苯衍生物。使用一步法，一锅法以适中的产率一步将合适的并苯醌转化为苯胺连接的并苯。发现迄今未报道的涉及形成二硫代氨基甲酸酯三烷基铵中间体的二硫化碳活化方法对于将这些并苯苯胺转化为并二苯并氨基甲酸酯是必不可少的。通过紫外/可见吸收和荧光光谱法评估了苯胺和二硫代氨基甲酸酯部分对所选并苯发色团的光物理性质的影响。