(3-hydroxyphenyl)triethylsilane | 167301-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3-hydroxyphenyl)triethylsilane
• 英文别名: 3-(triethylsilyl)phenol；m-triethylsilylphenol；3-Triethylsilylphenol
• CAS: 167301-29-3
• 化学式: C₁₂H₂₀OSi
• 分子量: 208.376
• InChiKey: GOGNVUVKJDNWRH-UHFFFAOYSA-N

物化性质

• 沸点：
  274.0±23.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 在 三溴化硼 、 对甲苯磺酸 、 2-(1H-3-吡唑)苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (3-hydroxyphenyl)triethylsilane
  参考文献：
  名称：

  히드록시아렌 붕소산 화합물의 열적 탈붕소수소화 및 이를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌 화합물의 제조방법

  摘要：

  This invention relates to a method for producing hydroxyarenes with introduced functional groups at the ortho or meta positions of phenolic compounds using the thermal deboronation of hydroxyarene boronic acid compounds. More specifically, the method involves substituting the ortho or para positions of phenol with boronic acid, introducing functional groups at the ortho or meta positions to produce hydroxyarene boronic acid compounds, and removing the boronic acid using thermal deboronation to obtain hydroxyarene compounds with functional groups at the ortho or meta positions. The method for producing hydroxyarene compounds according to this invention does not require metal catalysts such as palladium or iridium and does not involve harsh conditions such as strong acid or base, low temperature reactions, or anhydrous conditions, making it economical and simple to produce hydroxyarene compounds with functional groups at the ortho or meta positions from phenol.

  公开号：

  KR101572521B1

文献信息

• Photographic silver halide material containing a coupler having in a
  申请人：Eastman Kodak Company

  公开号：US05306604A1

  公开（公告）日：1994-04-26

  Photographic silver halide materials are disclosed comprising a support and a silver halide emulsion layer having associated therewith a coupler having in a non-coupling position a silyl substituent represented by the formula: ##STR1## wherein R.sub.1 through R.sub.4 individually are unsubstituted or substituted aliphatic, aromatic or heterocyclic groups, R.sub.5 is an unsubstituted or substituted aliphatic, aromatic or heterocyclic group which can be bonded to a non-coupling position of a second coupler moiety, and n=0, 1 or 2. In a preferred embodiment, the coupler is a photographic image dye-forming coupler. Processes for developing images in the photographic materials are also disclosed.

  公开了一种包括支撑体和银卤乳剂层的摄影银卤材料，其与具有非偶合位置的硅烷基取代基的偶联剂相关联，所述硅烷基取代基由以下式子表示：##STR1## 其中R.sub.1到R.sub.4分别是未取代或取代的脂肪族、芳香族或杂环基，R.sub.5是未取代或取代的脂肪族、芳香族或杂环基，可以与第二偶联剂基团的非偶合位置连接，并且n=0、1或2。在一种优选实施例中，偶联剂是摄影成像染料形成偶联剂。还公开了用于在摄影材料中开发图像的过程。
• Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups
  作者：Chun-Young Lee、Su-Jin Ahn、Cheol-Hong Cheon

  DOI：10.1021/jo402174v

  日期：2013.12.6

  The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.
• Direct and Selective Arylation of Tertiary Silanes with Rhodium Catalyst
  作者：Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1021/jo8008148

  日期：2008.9.1

  We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-alpha, is also described.
• 히드록시아렌 붕소산 화합물의 열적 탈붕소수소화 및 이를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌 화합물의 제조방법
  申请人：Korea University Research and Business Foundation 고려대학교 산학협력단(220040170680) BRN ▼209-82-08298

  公开号：KR101572521B1

  公开（公告）日：2015-11-27

  본 발명은 히드록시아렌 붕소산 화합물의 열적 탈붕소수소화를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌의 제조방법에 관한 것으로, 더욱 상세하게는 페놀의 오르소 또는 파라 위치를 붕소산으로 치환시킨 후, 오르소 또는 메타 위치에 작용기를 도입시켜 히드록시아렌 붕소산 화합물을 제조하고, 열적 탈붕소수소화를 이용하여 상기 붕소산을 제거함으로써 페놀로부터 오르소 또는 메타 위치에 작용기가 도입된 히드록시아렌 화합물을 제조하는 방법에 관한 것이다. 본 발명에 따른 히드록시아렌 화합물의 제조방법은 팔라듐이나 이리듐과 같은 금속촉매를 필요로 하지 않으며, 강한 산 또는 염기조건, 저온 반응 및 무수조건의 반응과 같은 까다로운 공정을 필요로 하지 않으므로 경제적이고, 간단하게 페놀로부터 오르소 또는 메타위치에 작용기를 도입시킨 히드록시아렌 화합물을 제조할 수 있다.

  This invention relates to a method for producing hydroxyarenes with introduced functional groups at the ortho or meta positions of phenolic compounds using the thermal deboronation of hydroxyarene boronic acid compounds. More specifically, the method involves substituting the ortho or para positions of phenol with boronic acid, introducing functional groups at the ortho or meta positions to produce hydroxyarene boronic acid compounds, and removing the boronic acid using thermal deboronation to obtain hydroxyarene compounds with functional groups at the ortho or meta positions. The method for producing hydroxyarene compounds according to this invention does not require metal catalysts such as palladium or iridium and does not involve harsh conditions such as strong acid or base, low temperature reactions, or anhydrous conditions, making it economical and simple to produce hydroxyarene compounds with functional groups at the ortho or meta positions from phenol.