2-(4-(triisopropyl)silyloxyphenyl)acetonitrile | 884320-49-4

• 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: 2-(4-(triisopropyl)silyloxyphenyl)acetonitrile
• 英文别名: 2-(4-triisopropylsilyloxyphenyl)acetonitrile；2-[4-Tri(propan-2-yl)silyloxyphenyl]acetonitrile
• CAS: 884320-49-4
• 化学式: C₁₇H₂₇NOSi
• 分子量: 289.493
• InChiKey: GDHYFFBYFMMGNP-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±25.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(triisopropyl)silyloxyphenyl)acetonitrile 在 N,N-二异丙基乙胺 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 copper diacetate 、 4 A molecular sieve 、 四丁基氟化铵 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 乙基苯 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 [2-(4-Phenoxyphenyl)-3-phenylpropyl]azanium;chloride
  参考文献：
  名称：

  Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

  摘要：

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

  DOI：

  10.1021/jm0700417
• 作为产物：
  描述：

  三异丙基氯硅烷 、 对羟基苯乙腈 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以84%的产率得到2-(4-(triisopropyl)silyloxyphenyl)acetonitrile
  参考文献：
  名称：

  Synthesis of [¹²⁵I]‐, [²H]‐, and [³H]‐Labeled 3‐Iodothyronamine (T₁AM)

  摘要：

  3-Iodothyronamine ( T(1)AM) is a novel metabolite of thyroid hormone. In HEK-293 cells expressing an orphan G-protein coupled receptor, the trace amine receptor, T(1)AM, potently increased cAMP accumulation. In mice, T(1)AM rapidly induced hypothermia and bradycardia within minutes of administration. These results suggest the existence of a new signaling pathway, the stimulation of which leads to rapid physiological and behavioral consequences. Isotope-labeled T(1)AM derivatives would be useful to study the biology and pharmacology of T(1)AM. Herein we describe efficient syntheses of [I-125]-, [H-2]-, and [H-3]- T(1)AM.

  DOI：

  10.1080/00397910500466074

文献信息

• Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1
  作者：Edwin S. Tan、Motonori Miyakawa、James R. Bunzow、David K. Grandy、Thomas S. Scanlan

  DOI：10.1021/jm0700417

  日期：2007.6.1

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.
• Synthesis of [¹²⁵I]‐, [²H]‐, and [³H]‐Labeled 3‐Iodothyronamine (T₁AM)
  作者：Motonori Miyakawa、Thomas S. Scanlan

  DOI：10.1080/00397910500466074

  日期：2006.3.1

  3-Iodothyronamine ( T(1)AM) is a novel metabolite of thyroid hormone. In HEK-293 cells expressing an orphan G-protein coupled receptor, the trace amine receptor, T(1)AM, potently increased cAMP accumulation. In mice, T(1)AM rapidly induced hypothermia and bradycardia within minutes of administration. These results suggest the existence of a new signaling pathway, the stimulation of which leads to rapid physiological and behavioral consequences. Isotope-labeled T(1)AM derivatives would be useful to study the biology and pharmacology of T(1)AM. Herein we describe efficient syntheses of [I-125]-, [H-2]-, and [H-3]- T(1)AM.