8-(2-trietoxysilylethyl)-6-methoxy-3,4-dihydro-1-2H-naphthalenone | 173612-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-(2-trietoxysilylethyl)-6-methoxy-3,4-dihydro-1-2H-naphthalenone
• 英文别名: 8-(2-(triethoxysilyl)ethyl)-3,4-dihydro-6-methoxy-1(2H)-naphthalenone；6-methoxy-8-(2-triethoxysilylethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 173612-80-1
• 化学式: C₁₉H₃₀O₅Si
• 分子量: 366.53
• InChiKey: XXNXCMICIICUED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-(2-trietoxysilylethyl)-6-methoxy-3,4-dihydro-1-2H-naphthalenone 在 potassium fluoride 、 双氧水 、 碳酸氢钠 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 2-[1-(3-methoxy-5,6,7,8-tetrahydronaphthalen-1-ol)]ethanol
  参考文献：
  名称：

  Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids

  摘要：

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00302-1
• 作为产物：
  描述：

  乙烯基三乙氧基硅烷 、 6-甲氧基-1-萘满酮 在 {ruthenium(0) dicarbonyltris(triphenylphosphine)} 作用下， 以 甲苯 为溶剂， 反应 38.0h， 以92%的产率得到8-(2-trietoxysilylethyl)-6-methoxy-3,4-dihydro-1-2H-naphthalenone
  参考文献：
  名称：

  Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; the functionalisation of ring C aromatic diterpenoids

  摘要：

  Ortho C-H bond coupling of some 2-alkoxyacetophenones with olefins catalysed by ruthenium complexes results in a high yield of the ortho alkylated product, providing that a suitable protecting group is employed. No such protection was required for a para-alkoxy group; an activating effect was also observed. Bicyclic and tricyclic analogues react similarly.

  DOI：

  10.1016/s0022-328x(96)06697-1

文献信息

• Functionalisation of Alkylalkoxysilanes. Studies Towards Annulations of Diterpenoids
  作者：Paul W.R. Harris、Paul D. Woodgate

  DOI：10.1016/s0040-4020(00)00302-1

  日期：2000.6

  Ortho-(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H2O2. Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH3. BMS, H2O2, Et3SiH/CF3COOH, TBAF) without isolation of intermediate products (oxasilepin, diol, trifluoroacetate). Use of the 14-(2-diethoxysilylmethyl) analogue improved the overall yield significantly (75 versus 40%). Re-oxidation of ring B with CAN gave the Delta(5)-7-oxo derivative, which was converted into an enone-aldehyde by treatment with Collins' reagent. The conjugated alkene was reduced stereoselectively with SmI2, which, however, did not promote pinacol coupling of the resulting 1,5-keto aldehyde. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; the functionalisation of ring C aromatic diterpenoids
  作者：Paul W.R. Harris、Paul D. Woodgate

  DOI：10.1016/s0022-328x(96)06697-1

  日期：1997.3

  Ortho C-H bond coupling of some 2-alkoxyacetophenones with olefins catalysed by ruthenium complexes results in a high yield of the ortho alkylated product, providing that a suitable protecting group is employed. No such protection was required for a para-alkoxy group; an activating effect was also observed. Bicyclic and tricyclic analogues react similarly.