2,2-Dimethyl-1,2,3,4-tetrahydro-2-silanaphthalene | 5136-93-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,2-Dimethyl-1,2,3,4-tetrahydro-2-silanaphthalene
• 英文别名: 2,2-dimethyl-2-silatetralin；2-silatetralin；2,2-dimethyl-1,2,3,4-tetrahydro-benzo[c]siline；2,2-dimethyl-2-sila-tetralin；2,2-Dimethyl-1,2,3,4-tetrahydro-2-sila-naphthalin；1,2,3,4-Tetrahydro-2,2-dimethyl-2-silanaphthalene；2,2-dimethyl-3,4-dihydro-1H-2-benzosiline
• CAS: 5136-93-6
• 化学式: C₁₁H₁₆Si
• 分子量: 176.334
• InChiKey: QGILQJWXGXFGSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  227-229 °C
• 沸点：
  244.0±29.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-1,2,3,4-tetrahydro-2-silanaphthalene 在 三氯化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 6-acetoxy-2,2-dimethyl-2-silatetralin
  参考文献：
  名称：

  Synthesis of 6-Acyl-2, 2-dimethyl-2-silatetralins

  摘要：

  Friedel-Crafts reaction of 2-silatetralin (4) with acid anhydrides (acetic anhydride, succinic anhydride, glutaric anhydride, phthalic anhydride, cis-1, 2-cyclohexanedicarboxylic an hydride, and diphenic anhydride) or benzoyl chloride in the presence of AICl(3) in CH2Cl2 at room temperature gave exclusively the corresponding 6-acyl-2-silatetralins in fair to good yield. This findings were supported by the MNDO molecular orbital calculations of 2-silatetralin (4).

  DOI：

  10.3987/com-95-7271
• 作为产物：
  描述：

  2-<(Trimethylsilyl)methyl>benzaldehyde 在 sodium hydride 作用下， 以 甲醇 为溶剂， 25.0~300.0 ℃ 、0.13 Pa 条件下， 反应 24.5h， 生成 2,2-Dimethyl-1,2,3,4-tetrahydro-2-silanaphthalene
  参考文献：
  名称：

  Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene

  摘要：

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).

  DOI：

  10.1021/jo00093a014

文献信息

• Synthesis of N-Methylphenanthridinone Derivatives Fused with a Silacyclohexane Ring by Radical Reaction Using Tributyltin Hydride
  作者：Osamu Hoshino、Yuya Hoshino

  DOI：10.3987/com-05-s(k)64

  日期：——

  Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6-and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dim

  (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratraamide (8a) 和 -piperonamides (8b) 在沸腾的苯中使用氢化三丁基锡和 AIBN 进行自由基反应，得到两种 N-甲基菲啶酮衍生物（15 和 16），它们在芳酸部分的 6 位和 2 位环化。另一方面，N-甲基-N-(2-溴代甲基和2-溴哌啶基)-2,2-二甲基-2-silatetralin-6-carboxamides (14) 的类似反应分别产生 N-甲基菲啶酮衍生物 (17)唯一的产物，其中环化发生在 2-silatetralin 部分的 5 位。
• Radical-Induced Formation of Some Siloles and Diazasiloles
  作者：Bangwei Ding、Zhu Teng、Reinhart Keese

  DOI：10.1021/jo0202684

  日期：2002.12.1

  reaction of o-iodobenzylvinylsilanes and o-iodoallylsilanes leads to cyclic products in yields of 40-60%. These regioselective cyclizations occur with high preference for a 5-exo and a 7-endo mode with a 6-exo mode being absent. An example for ring closure via a 7-exo mode is described.

  Bu（3）Sn自由基诱导的邻碘苄基乙烯基硅烷和邻碘烯丙基硅烷反应导致环状产物的收率为40-60％。这些区域选择性环化以5-exo和7-endo模式的优先出现，而缺少6-exo模式。描述了通过7-exo模式关闭环的示例。
• Hirokawa, Akihisa; Tatsuno, Atsuhiro; Hoshino, Osamu, Heterocycles, 1994, vol. 38, # 5, p. 1103 - 1118
  作者：Hirokawa, Akihisa、Tatsuno, Atsuhiro、Hoshino, Osamu

  DOI：——

  日期：——
• Kirmse, Wolfgang; Konrad, Wolfgang, Angewandte Chemie, 1990, vol. 102, # 6, p. 682 - 683
  作者：Kirmse, Wolfgang、Konrad, Wolfgang

  DOI：——

  日期：——
• Carbon magnetic resonance of organometallic Compounds: Hyperconjugative effects in benzylsilanes
  作者：S.Q.A. Rizvi、B.D. Gupta、William Adcock、David Doddrell、William Kitching

  DOI：10.1016/s0022-328x(73)80019-1

  日期：1973.12