1-chlorosilatrane | 33446-81-0

• 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: 1-chlorosilatrane
• 英文别名: chlorosilatrane；1-chloro-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane；(TB-5-13)-(2,2',2''-azanetriyl-tris-ethanolato(3-)-N,O,O',O'')-chloro-silicon；1-Chlorsilatran；2,8,9-Trioxa-5-aza-1-silabicyclo(3.3.3)undecane, 1-chloro-；1-chloro-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane
• CAS: 33446-81-0
• 化学式: C₆H₁₂ClNO₃Si
• 分子量: 209.705
• InChiKey: QNZCOBXMTUNWKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-chlorosilatrane 在 potassium fluoride 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 14.0h， 以80%的产率得到1-fluorosilatrane
  参考文献：
  名称：

  1-卤素

  摘要：

  讨论了1-卤代硅烷基酯的电子结构。描述了一些新的制备方法，这些方法基于硅烷基烃以及被硅和碳取代的硅烷基与卤化试剂的异溶和均溶反应，还描述了从某些有机三烷氧基和有机三氯硅烷合成1-卤代硅烷基的方法。已经研究了1-碘硅杂环丁烷与醚和酯，羰基化合物，烷氧基硅烷和硅氧烷，末端炔烃和有机汞的亲电反应。

  DOI：

  10.1016/0022-328x(88)87069-4
• 作为产物：
  描述：

  1-甲基-2,8,9-三氧杂-5-氮杂-1-硅杂二环[3.3.3]十一烷 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到1-chlorosilatrane
  参考文献：
  名称：

  溴或氯化碘在 1-有机基硅烷中的 Si-C-Bond 裂解

  摘要：

  I-有机基硅烷中的 Si-C 键被溴或氯化碘裂解，分别生成 1-溴或 1-氯硅烷。在 Et2O 或 THF 存在下，在二溴化二恶烷的作用下，I-卤代硅油

  DOI：

  10.1007/bf01457789

文献信息

• Pentacoordinate silicon compounds. Reactions of silatranes with nucleophiles
  作者：G. Cerveau、C. Chuit、R.J.P. Corriu、N.K. Nayyar、C. Reye

  DOI：10.1016/0022-328x(90)85408-q

  日期：1990.6

  studied. Substitution involving cleavage of equatorial SiO bonds is always observed. Silatranes exhibit reactivity quite different from that of analogous trialkoxysilanes or anionic pentacoordinate silicon compounds.

  已经研究了氢，有机基和卤代硅烷基团与亲核试剂的反应。总是观察到涉及赤道SiO键断裂的取代。Silatranes的反应性与类似的三烷氧基硅烷或阴离子五配位硅化合物完全不同。
• Iodochlorination of silyl- and germylphenylacetylenes
  作者：Anastasia A. Selina、Anna E. Zhachkina、Sergey S. Karlov、Andrei V. Churakov、Galina S. Zaitseva

  DOI：10.1002/hc.20001

  日期：——

  Reactions of Si- and Ge-substituted alkynes with KICl2 were investigated. (1-Germatranyl)-phenylacetylenes and (triphenylsilyl)phenylacetylene gave Z-iodochloroalkenes with chlorine and phenyl groups attached to the same carbon atom. Adduct structures were confirmed by X-ray diffraction studies. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:169–174, 2004; Published online in Wiley InterScience

  研究了 Si 和 Ge 取代的炔烃与 KICl 2 的反应。(1-Germatranyl)-苯基乙炔和(三苯基甲硅烷基)苯基乙炔得到氯和苯基连接到同一碳原子上的Z-碘氯烯烃。X 射线衍射研究证实了加合物结构。© 2004 Wiley Periodicals, Inc. 杂原子化学 15:169–174, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20001
• Reactions of 1-hydro-and 1-halosilatranes with metal salts
  作者：N. F. Lazareva、V. A. Pestunovich

  DOI：10.1007/s11172-006-0326-8

  日期：2006.4

  1-Hydrosilatrane reduces AgNO3 and CuCl2 in CH3CN to form metallic silver and CuCl, respectively; other reaction products are the silatranyl nitrate O2NOSi(OCH2CH2)3N and the 1-chlorosilatrane ClSi(OCH2CH2)3N.

  1-氢硅烷烃在CH3CN中还原AgNO3和CuCl2，分别形成金属银和CuCl；其他反应产物为硅烷基硝酸酯O2NOSi(OCH2CH2)3N和1-氯硅烷烃ClSi(OCH2CH2)3N。
• Silane: A new linker for chromophores in dye-sensitised solar cells
  作者：Katherine Szpakolski、Kay Latham、Colin Rix、Rozina A. Rani、Kourosh Kalantar-zadeh

  DOI：10.1016/j.poly.2012.07.078

  日期：2013.3

  A series of ruthenium(II) polypyridyl complexes, with novel silane functionalisation, [Ru(bipy)(2)(bipy-sil)] (PF6)(2) (3), [Ru(bipy-sil)(2)Cl-2] (6), and [Ru(bipy-sil)(2)(NCS)(2)] (7) have been synthesised and tested as chromophores (dyes) in TiO2 and WO3 based dye-sensitised solar cells (DSSCs). The performance of the respective DSSCs were compared to analogous dyes with ionic carboxylate ([Ru(bipy)(2)(dcbipy)](PF6)(2) (1), [Ru(dcbipy)(2)Cl-2] (4), [Ru(dcbipy)(2)(NCS)(2)] (5)) or phosphonate ([Ru(bipy)(2)(dpipy)](PF6)(2) (2)) linking groups. The covalent silane-metal oxide linkage offers much needed improvement to the operating conditions, and lifetime of DSSCs, in terms of pH range and choice of solvent. UV-Vis spectroscopy of the deep-red solutions showed that the bis-bipy-sil complexes absorbed more visible light than the tris-bipy complex, as indicated by the presence of two absorption bands and higher E values. The UV-Vis spectrum of (3) contained a single broad absorption at 400-600 nm with: lambda(max) = 457 nm; epsilon = 10520 +/- 440 L mol(-1) cm(-1), whereas two intense broad absorption bands were observed for novel bis-bipy-sil complexes (6): 340-370 nm (lambda(max(1)) = 365 nm, epsilon((1)) = 12716 +/- 180 L mol(-1) cm(-1)); and 440-540 nm (lambda(max(2)) = 485 nm, epsilon((2)) = 11070 +/- 150 L mol(-1) cm(-1)), and (7): 340-400 nm (lambda(max) = 371 nm epsilon((1)) = 20690 +/- 485 L mol(-1) cm(-1)), and 460-530 nm (lambda(max) = 500 nm and epsilon((2)) = 20750 +/- 487 L mol(-1) cm(-1)). The bands in (7) being significantly more defined.A 10-fold improvement in the efficiency of the bipy-sil TiO2-based DSSCs was observed from (3) to (6) to (7). This performance was lower than that of the commercial N3 dye, [Ru(dcbipy)(2)(NCS)(2)] (5), but the current of (7) on WO3, was comparable to that of the carboxylate system (4). There is considerable potential for further improvement by modification of the silyl linker, reducing the long non-conjugated propyl chain between the amide group and the silatrane (bipy-sil), to a short, conjugated link. During an extensive synthetic study, the most promising strategy was identified as direct linkage, the formation of a direct Si-C bond, using butyllithium with 4,4'-dibromo-2,2'-bipyridine and either trimethylsilane or 1-ethoxysilatrane, provided that the product can be captured and stabilised prior to binding to a metal oxide coated DSSC substrate. (C) 2012 Elsevier Ltd. All rights reserved.
• Reactions of 1-iodosilatrane with organomercury compounds
  作者：M. G. Voronkov、V. A. Pestunovich、L. P. Petukhov、V. I. Rakhlin

  DOI：10.1007/bf00953128

  日期：1983.3