r-5-tert-Butyl-t-2-(trimethylsilyl)cyclohex-t-yl p-nitrobenzoate | 142743-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: r-5-tert-Butyl-t-2-(trimethylsilyl)cyclohex-t-yl p-nitrobenzoate
• 英文别名: [(1R,2S,5S)-5-tert-butyl-2-trimethylsilylcyclohexyl] 4-nitrobenzoate
• CAS: 142743-99-5；142744-02-3；142761-42-0
• 化学式: C₂₀H₃₁NO₄Si
• 分子量: 377.556
• InChiKey: GDNGZBARODNZRV-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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 吡啶 、 乙醚 为溶剂， 生成 r-5-tert-Butyl-t-2-(trimethylsilyl)cyclohex-t-yl p-nitrobenzoate
  参考文献：
  名称：

  Stereoelectronic effect of the trimethylsilyl substituent upon carbon-oxygen bond lengths at the .beta. position: some structural studies

  摘要：

  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.

  DOI：

  10.1021/jo00043a020

文献信息

• 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.