3-tert-butyldiphenylsilyloxypropionic acid | 352708-78-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-tert-butyldiphenylsilyloxypropionic acid
• 英文别名: 3-(tert-Butyl-diphenyl-silanyl)-propionic acid；3-[Tert-butyl(diphenyl)silyl]propanoic acid
• CAS: 352708-78-2
• 化学式: C₁₉H₂₄O₂Si
• 分子量: 312.484
• InChiKey: FXHLKZRJPKUCTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-tert-butyldiphenylsilyloxypropionic acid 在 三氟甲磺酸 、 三甲基乙酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(tert-Butyl-hydroxy-phenyl-silanyl)-N,N-dimethyl-propionamide
  参考文献：
  名称：

  Studies in silanol synthesis: internal nucleophiles and steric hindrance

  摘要：

  As a model system for the synthesis of complex silanediols, N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide was prepared and treated with triflic acid, resulting in the removal of one phenyl group and yielding a silanol. Even with a large excess of triflic acid, only a single phenyl group could be removed. This contrasts with a diphenylsilyl group flanked by a pair of amides, for which both phenyl groups are rapidly cleaved. A combination of steric hindrance by the tert-butyl group and lack of a second internal nucleophile appears to limit triflic acid-mediated phenyl hydrolysis from the silicon. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00576-7
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyl)propene 在 sodium hydroxide 、 potassium permanganate 、 四丙基高钌酸铵 、 硼烷 、 双氧水 作用下， 生成 3-tert-butyldiphenylsilyloxypropionic acid
  参考文献：
  名称：

  Studies in silanol synthesis: internal nucleophiles and steric hindrance

  摘要：

  As a model system for the synthesis of complex silanediols, N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide was prepared and treated with triflic acid, resulting in the removal of one phenyl group and yielding a silanol. Even with a large excess of triflic acid, only a single phenyl group could be removed. This contrasts with a diphenylsilyl group flanked by a pair of amides, for which both phenyl groups are rapidly cleaved. A combination of steric hindrance by the tert-butyl group and lack of a second internal nucleophile appears to limit triflic acid-mediated phenyl hydrolysis from the silicon. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00576-7

文献信息

• C. elegans as a model for inter-individual variation in metabolism
  作者：Bennett W. Fox、Olga Ponomarova、Yong-Uk Lee、Gaotian Zhang、Gabrielle E. Giese、Melissa Walker、Nicole M. Roberto、Huimin Na、Pedro R. Rodrigues、Brian J. Curtis、Aiden R. Kolodziej、Timothy A. Crombie、Stefan Zdraljevic、L. Safak Yilmaz、Erik C. Andersen、Frank C. Schroeder、Albertha J. M. Walhout

  DOI：10.1038/s41586-022-04951-3

  日期：2022.7.21

  Individuals can exhibit differences in metabolism that are caused by the interplay of genetic background, nutritional input, microbiota and other environmental factors1–4. It is difficult to connect differences in metabolism to genomic variation and derive underlying molecular mechanisms in humans, owing to differences in diet and lifestyle, among others. Here we use the nematode Caenorhabditis elegans as a model to study inter-individual variation in metabolism. By comparing three wild strains and the commonly used N2 laboratory strain, we find differences in the abundances of both known metabolites and those that have not to our knowledge been previously described. The latter metabolites include conjugates between 3-hydroxypropionate (3HP) and several amino acids (3HP-AAs), which are much higher in abundance in one of the wild strains. 3HP is an intermediate in the propionate shunt pathway, which is activated when flux through the canonical, vitamin-B12-dependent propionate breakdown pathway is perturbed5. We show that increased accumulation of 3HP-AAs is caused by genetic variation in HPHD-1, for which 3HP is a substrate. Our results suggest that the production of 3HP-AAs represents a ‘shunt-within-a-shunt’ pathway to accommodate a reduction-of-function allele in hphd-1. This study provides a step towards the development of metabolic network models that capture individual-specific differences of metabolism and more closely represent the diversity that is found in entire species. Using differences among strains as a model for inter-individual variation, this paper identifies a conserved metabolicadaptation in C. elegans that compensates for genetic variation.

  个体之间的新陈代谢差异可能是由遗传背景、营养摄入、微生物群和其他环境因素相互作用引起的1-4。由于饮食和生活方式等方面的差异，很难将新陈代谢的差异与基因组变异联系起来，并从中得出人类潜在的分子机制。在这里，我们以线虫秀丽隐杆线虫（Caenorhabditis elegans）为模型，研究个体之间的新陈代谢差异。通过比较三个野生菌株和常用的N2实验室菌株，我们发现已知代谢物和那些以前未知的代谢物的丰度存在差异。后者包括3-羟基丙酸盐（3HP）和几种氨基酸（3HP-AAs）之间的结合物，其中一种野生菌株中的含量要高得多。3HP是丙酸盐分流途径的中间产物，当通过典型的、维生素B12依赖的丙酸盐分解途径的通量受到干扰时，丙酸盐分流途径就会被激活5。我们表明，3HP-AAs的积累增加是由HPHD-1的遗传变异引起的，而3HP是HPHD-1的底物。我们的结果表明，3HP-AAs的产生代表了一种“分流中的分流”途径，以适应hphd-1中功能降低的等位基因。这项研究为开发代谢网络模型迈出了一步，该模型可以捕捉个体特定的代谢差异，并更准确地反映整个物种的多样性。本文以菌株之间的差异为个体差异模型，确定了秀丽隐杆线
• Studies in silanol synthesis: internal nucleophiles and steric hindrance
  作者：Athanasios Glekas、Scott McN Sieburth

  DOI：10.1016/s0040-4039(01)00576-7

  日期：2001.6

  As a model system for the synthesis of complex silanediols, N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide was prepared and treated with triflic acid, resulting in the removal of one phenyl group and yielding a silanol. Even with a large excess of triflic acid, only a single phenyl group could be removed. This contrasts with a diphenylsilyl group flanked by a pair of amides, for which both phenyl groups are rapidly cleaved. A combination of steric hindrance by the tert-butyl group and lack of a second internal nucleophile appears to limit triflic acid-mediated phenyl hydrolysis from the silicon. (C) 2001 Published by Elsevier Science Ltd.