(diphenyl)(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)silane | 1062504-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (diphenyl)(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)silane
• 英文别名: diphenyl(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)silane；diphenyl[3-(tetrahydro-2H-pyran-2-yloxy)propyl]silane；3-(Oxan-2-yloxy)propyl-diphenylsilane
• CAS: 1062504-87-3
• 化学式: C₂₀H₂₆O₂Si
• 分子量: 326.511
• InChiKey: CQDWGYDLXLRYBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (diphenyl)(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)silane 在 盐酸 、 ruthenium trichloride 、 sodium periodate 、 lithium 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 3-[[(1R)-3-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-diphenylsilyl]propanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Silanediols as Highly Selective Uncompetitive Inhibitors of Human Neutrophil Elastase

  摘要：

  Chronic obstructive pulmonary disease (COPD) is an increasing health problem and is estimated to be the fifth leading cause of death in 2020 according to the World Health Organization. Current treatments are only palliative, and therefore the development of new medicine for the treatment of COPD is urgent. Human Neutrophil Elastase (HNE) is a serine protease that is heavily involved in the progression of COPD through inflammatory breakdown of lung tissue. Consequently, inhibitors of HNE are of great interest as therapeutics. In this article, the development of silanediol peptide isosters as inhibitors of HNE is presented. Kinetic studies revealed that incorporation of a silanediol isoster in the inhibitor structure resulted in an uncompetitive mechanism of inhibition, which further resulted in excellent selectivity. The peculiar mechanism of inhibition and the resulting selectivity makes the presented inhibitors promising leads for the development of new FINE-inhibitor-based therapeutics for the treatment of COPD.

  DOI：

  10.1021/jm301000k
• 作为产物：
  描述：

  2-丙烯氧基吡喃 、 二苯基硅烷 在 Wilkinson's catalyst 作用下， 以 四氢呋喃 为溶剂， 生成 (diphenyl)(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)silane
  参考文献：
  名称：

  Synthesis and Evaluation of Silanediols as Highly Selective Uncompetitive Inhibitors of Human Neutrophil Elastase

  摘要：

  Chronic obstructive pulmonary disease (COPD) is an increasing health problem and is estimated to be the fifth leading cause of death in 2020 according to the World Health Organization. Current treatments are only palliative, and therefore the development of new medicine for the treatment of COPD is urgent. Human Neutrophil Elastase (HNE) is a serine protease that is heavily involved in the progression of COPD through inflammatory breakdown of lung tissue. Consequently, inhibitors of HNE are of great interest as therapeutics. In this article, the development of silanediol peptide isosters as inhibitors of HNE is presented. Kinetic studies revealed that incorporation of a silanediol isoster in the inhibitor structure resulted in an uncompetitive mechanism of inhibition, which further resulted in excellent selectivity. The peculiar mechanism of inhibition and the resulting selectivity makes the presented inhibitors promising leads for the development of new FINE-inhibitor-based therapeutics for the treatment of COPD.

  DOI：

  10.1021/jm301000k

文献信息

• Further Studies toward the Stereocontrolled Synthesis of Silicon-Containing Peptide Mimics
  作者：Dácil Hernández、Karl B. Lindsay、Lone Nielsen、Tina Mittag、Klaus Bjerglund、Stig Friis、Rasmus Mose、Troels Skrydstrup

  DOI：10.1021/jo100301n

  日期：2010.5.21

  Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate

  为了制备各种基于硅烷二醇的蛋白酶抑制剂，进一步报道了利用手性亚磺胺和烷基二苯基甲硅烷基锂试剂之间的通用反应的研究。尤其是，已将重点放在展示如何将许多遗传编码的氨基酸侧链（如丝氨酸，苏氨酸，酪氨酸，赖氨酸，脯氨酸，精氨酸，天冬氨酸和天冬酰胺）整合到整个方法中。还描述了应用这种合成方法来获得生物学相关的硅烷二醇二肽模拟物的努力。这包括人嗜中性粒细胞弹性蛋白酶的潜在抑制剂的合成，以及人胰岛淀粉样多肽的六肽片段的二苯基硅烷模拟物。
• Nielsen, Lone; Skrydstrup, Troels, Journal of the American Chemical Society, 2008, vol. 130, p. 13145 - 13151
  作者：Nielsen, Lone、Skrydstrup, Troels

  DOI：——

  日期：——
• Regioselective Rh(I)-Catalyzed Sequential Hydrosilylation toward the Assembly of Silicon-Based Peptidomimetic Analogues
  作者：Geanna K. Min、Troels Skrydstrup

  DOI：10.1021/jo300904z

  日期：2012.7.20

  A highly regioselective Rh(I)-catalyzed hydrosilylation of enamides is presented. This mild protocol allows access to a wide variety of different arylsilanes with substitution at the beta-position of the enamide and functionalization on the alkyl chain tethered to the silane. This protocol is extended to include a sequential one-pot hydrosilylation. Using diphenylsilane as the appendage point, hydrosilylation of a protected allyl alcohol followed by hydrosilylation of an enamide generates a complex organosilane in one step. This highly convergent strategy to synthesize these functionalized systems now provides a way for the rapid assembly of a diverse collection of silane-based peptidomimetic analogues.
• Stereocontrolled Synthesis of 2-Substituted-1,3-Azasilaheterocycles
  作者：Dácil Hernández、Lone Nielsen、Karl B. Lindsay、M. Ángeles López-García、Klaus Bjerglund、Troels Skrydstrup

  DOI：10.1021/ol101379t

  日期：2010.8.6

  Chiral alpha-silylsulfinamides, prepared by the treatment of an alkyldiphenylsilane with lithium followed by its addition to a sulfinimine, can be applied to the synthesis of 1,3-azasilaheterocycles as derivatives of cyclic alkaloids. This synthetic route, which involves intramolecular substitution of an amino alcohol or cyclization of an amino acid promoted by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), represents a convenient means for accessing these silicon-containing heterocycles.