3,4-diphenyl-3,4-bis(trimethylsilyloxy)-1,1,2,2-tetrakis(trimethylsilyl)-1,2-disilacyclobutane | 60154-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-diphenyl-3,4-bis(trimethylsilyloxy)-1,1,2,2-tetrakis(trimethylsilyl)-1,2-disilacyclobutane
• 英文别名: 3,4-diphenyl-1,1,2,2-tetrakis-trimethylsilanyl-3,4-bis-trimethylsilanyloxy-[1,2]disiletane；1,1,2,2-Tetra(trimethylsilyl)3,4-bis(trimethylsiloxy)3,4-diphenyl-1,2-silacyclobutane；[3,4-diphenyl-1,1,2,2-tetrakis(trimethylsilyl)-4-trimethylsilyloxydisiletan-3-yl]oxy-trimethylsilane
• CAS: 60154-99-6
• 化学式: C₃₂H₆₄O₂Si₈
• 分子量: 705.543
• InChiKey: HCUFISVPUOPSPK-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  553.2±60.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.21
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-3,4-bis(trimethylsilyloxy)-1,1,2,2-tetrakis(trimethylsilyl)-1,2-disilacyclobutane 、 2,2-二甲基丙基次基膦 以 甲苯 为溶剂， 90.0 ℃ 、500.0 kPa 条件下， 反应 6.0h， 以75%的产率得到1a--silyl-6,7-di-t-butyl-1aH,6H-1,6a-methanocyclopropainden
  参考文献：
  名称：

  Organophosphorverbindungen LXXIII . Abfangreaktion eines “in situ” erzeugten Silens mit tBuCP. Bildung eines Diphosphatricyclobenzoheptans

  摘要：

  Silene 5 can be generated thermally from the disilacyclobutane 4 by [2 + 2] cycloreversion and trapped by reaction with two equivalents of phosphaalkyne 2 under formation of the disphosphatricyclobenzoheptane 6. Low-temperature X-ray crystal structure analysis,confirms the result. A plausible reaction mechanism, based above all on cycloaddition steps and an ene reaction, is presented.

  DOI：

  10.1016/0022-328x(94)87006-3
• 作为产物：
  描述：

  benzoyltris(trimethylsilyl)silane 以 环己烷 为溶剂， 反应 2.0h， 以43%的产率得到3,4-diphenyl-3,4-bis(trimethylsilyloxy)-1,1,2,2-tetrakis(trimethylsilyl)-1,2-disilacyclobutane
  参考文献：
  名称：

  Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping

  摘要：

  描述了一种从简单醛生成高度反应性瞬态硅烯的健全且可靠的序列阐明。关键步骤涉及硅基改性彼得森烯化，这在很大程度上依赖于存在亚化学计量的可溶性锂盐（LiBr）。

  DOI：

  10.1039/b404166f

文献信息

• Relatively stable silaethylenes. Photolysis of acylpolysilanes
  作者：Adrian G. Brook、John W. Harris、John Lennon、Maher El Sheikh

  DOI：10.1021/ja00495a015

  日期：1979.1
• RICHTER, HANS;ARENZ, STEFAN;MICHELS, GISBERT;SCHNEIDER, JURGEN;WAGNER, OL+, CHEM. BER., 121,(1988) N 7, C. 1363-1365
  作者：RICHTER, HANS、ARENZ, STEFAN、MICHELS, GISBERT、SCHNEIDER, JURGEN、WAGNER, OL+

  DOI：——

  日期：——
• The mass spectra of some tris(trimethylsilyl)acylsilanes and tris(trimethylsilyl)silanes
  作者：Adrian G. Brook、Alex. G. Harrison、R. Krishna M. R. Kallury

  DOI：10.1002/oms.1210170803

  日期：1982.8

  AbstractWhile tris(trimethylsilyl) alkanoylsilanes fragment in the acylsilane form yielding [(Me3Si)3SiCO]+ by α‐cleavage, the molecular ions of their aryl counterparts rearrange to ionized silaethenes prior to cleavage, paralleling known photochemical behaviour. Sila‐allyl type structures are attributed to the stable [MMe˙]+ ions obtained by subsequent cleavage. Metastable ion characteristics reveal the identity of the structures of the monomeric silaethene ions obtained from one of the aroylsilanes and a 1,2‐disilacyclobutane. The non‐compliance of the alkanoylsilanes with their photochemical behaviour is attributed to a preferred elimination of the stable alkyl radical (R˙) from the molecular ions. Several polysilanes display abundant odd‐electron ions which may possess a disilene structure.
• Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping
  作者：Malcolm B. Berry、Russell J. Griffiths、Mahesh J. Sanganee、Patrick G. Steel、Daniel K. Whelligan

  DOI：10.1039/b404166f

  日期：——

  The elucidation of a robust and reliable sequence for the generation of highly reactive transient silenes from simple aldehydes is described. The key step involves a silyl-modified Peterson olefination which critically depends on the presence of a sub-stoichiometric amount of soluble lithium salts (LiBr).

  描述了一种从简单醛生成高度反应性瞬态硅烯的健全且可靠的序列阐明。关键步骤涉及硅基改性彼得森烯化，这在很大程度上依赖于存在亚化学计量的可溶性锂盐（LiBr）。
• Organophosphorverbindungen LXXIII . Abfangreaktion eines “in situ” erzeugten Silens mit tBuCP. Bildung eines Diphosphatricyclobenzoheptans
  作者：Bernhard Breit、Roland Boese、Manfred Regitz

  DOI：10.1016/0022-328x(94)87006-3

  日期：1994.1

  Silene 5 can be generated thermally from the disilacyclobutane 4 by [2 + 2] cycloreversion and trapped by reaction with two equivalents of phosphaalkyne 2 under formation of the disphosphatricyclobenzoheptane 6. Low-temperature X-ray crystal structure analysis,confirms the result. A plausible reaction mechanism, based above all on cycloaddition steps and an ene reaction, is presented.