1-(trimethylsilyl)-4-tert-butyl-7-oxa-cis-bicyclo<4.1.0>heptane | 66255-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1-(trimethylsilyl)-4-tert-butyl-7-oxa-cis-bicyclo<4.1.0>heptane
• 英文别名: 4-tert-butyl-1-(trimethylsilyl)cyclohexene oxide；4-t-butyl-1-trimethylsilyl-7-oxabicyclo<4.1.0>heptane；1-Trimethylsilyl-4-t-butylcyclohexen-epoxid；(4-tert-butyl-7-oxabicyclo[4.1.0]heptan-1-yl)-trimethylsilane
• CAS: 66255-13-8
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: FEPJVXNLDWTNKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilyl)-4-tert-butyl-7-oxa-cis-bicyclo<4.1.0>heptane 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 生成 r-5-tert-Butyl-t-2-(trimethylsilyl)cyclohexan-t-ol
  参考文献：
  名称：

  Stabilization of positive charge by .beta.-silicon

  摘要：

  DOI：

  10.1021/ja00259a036
• 作为产物：
  描述：

  1-chloro-4-tert-butylcyclohexene 在 sodium 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-(trimethylsilyl)-4-tert-butyl-7-oxa-cis-bicyclo<4.1.0>heptane
  参考文献：
  名称：

  Stabilization of positive charge by .beta.-silicon

  摘要：

  DOI：

  10.1021/ja00259a036

文献信息

• Some epoxide ring-opening reactions of αβ-epoxysilanes
  作者：Anthony P. Davis、Gwyneth J. Hughes、Peter R. Lowndes、Catherine M. Robbins、Elizabeth J. Thomas、Gordon H. Whitham

  DOI：10.1039/p19810001934

  日期：——

  Epoxide ring-opening of 1,2-epoxy-1-trimethylsilylcyclohexane (3) has given a range of the 2-substituted 2-trimethylsilylcyclohexanols (4; X = H, OH, OMe, OCH2CHCH2, Br, I, SCN) in which attack by nucleophile has occurred at the carbon α to silicon. The products (4) have been transformed into a number of functionalised silanes, including the silyl-episulphide (9). Other epoxides which have been less

  1,2-环氧-1-三甲基甲硅烷基环己烷（3）的环氧开环给出了一系列2-取代的2-三甲基甲硅烷基环己醇（4; X = H，OH，OMe，OCH 2 CH CH 2，Br，I， SCN），其中亲核试剂的攻击发生在碳原子对硅的α处。产物（4）已被转化为许多官能化的硅烷，包括甲硅烷基-环二硫化物（9）。尚未进行广泛研究的其他环氧化物是结构偏倚的环氧硅烷（10）和（11），八元环环氧硅烷（17）和（21）以及两种立体异构体2,3-环氧-3-三甲基甲硅烷基戊烷（26）和（29）。用H +处理后获得环氧开环加合物除化合物（17）以外，所有情况下均为-MeOH，其中双环醇（18）通过环过环反应形成。
• Epoxidation versus Allylic Oxidation (CH Insertion) in the Oxyfunctionalization of Vinylsilanes and β-Hydroxy Derivatives by Dimethyldioxirane
  作者：W Adam

  DOI：10.1016/00404-0399(50)0960k-

  日期：1995.7.10
• Stereoelectronic effect of the trimethylsilyl substituent upon carbon-oxygen bond lengths at the .beta. position: some structural studies
  作者：Jonanthan M. White、Glen B. Robertson

  DOI：10.1021/jo00043a020

  日期：1992.8

  Results of low-temperature (130 K) crystal structure analyses for seven beta-trimethylsilyl-substituted cyclo-hexylnitrobenzoate esters are reported. For those molecules (three) with the Si-C and C-O bonds antiperiplanar the C-O bond lengths are increased by 0.014 angstrom av (DELTA/sigma min = 2.9) compared with that in the silicon-free For those molecules (four) with the Si-C and C-O bonds gauche no such systematic lengthening of the C-O bonds is observed. The result is in qualitative agreement with that [DELTA-l is-proportional-to cos2 (Si-C-C-O)] predicted from semiempirical MO calculations on a simple model complex and is attributed to the effects of interactions between the Si-C sigma and C-O sigma* orbitals. It is suggested that existence of the observed ground-state effect constitutes persuasive, if circumstantial, evidence that the major kinetic effects known to result from the presence of a beta silicon substituent also have their genesis in the same sigma-sigma* interactions.
• Silanes in organic synthesis. 9. Enesilylation as a method for 1,2-carbonyl migration within ketones and for conversion to 1,2-transposed allylic alcohols
  作者：William E. Fristad、Thomas R. Bailey、Leo A. Paquette

  DOI：10.1021/jo01303a021

  日期：1980.7