((5,5-dimethylhexyl)oxy)trimethylsilane | 42496-19-5

• 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: ((5,5-dimethylhexyl)oxy)trimethylsilane
• 英文别名: 5,5-Dimethylhexoxy(trimethyl)silane
• CAS: 42496-19-5
• 化学式: C₁₁H₂₆OSi
• 分子量: 202.412
• InChiKey: FOXKHEFRXLPRNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  194.6±8.0 °C(Predicted)
• 密度：
  0.802±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((5,5-dimethylhexyl)oxy)trimethylsilane 在 甲烷磺酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 5,5-二甲基-1-己醇
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888
• 作为产物：
  描述：

  三甲基氯硅烷 、 5,5-二甲基-1-己醇 在 吡啶 作用下， 以 乙醚 为溶剂， 生成 ((5,5-dimethylhexyl)oxy)trimethylsilane
  参考文献：
  名称：

  Pola,J. et al., Collection of Czechoslovak Chemical Communications, 1974, vol. 39, p. 3705 - 3710

  摘要：

  DOI：

文献信息

• Novel and facile syntheses of t-butyl substituted silanes from t-butyl magnesium chloride and chlorosilanes catalyzed by cuprous cyanide
  作者：Akihiko Shirahata

  DOI：10.1016/s0040-4039(01)93903-6

  日期：1989.1

  t-Butyl substituted silanes, e.g. t-butyldimethylchlorosirane, were successfully obtained by cuprous chloride promoted coupling reaction of t-butyl Grignard reagent and chlorosilanes.

  通过氯化亚铜促进格氏试剂与氯硅烷的偶联反应，成功地获得了叔丁基取代的硅烷，例如叔丁基二甲基氯硅烷。
• Tuning Reactivities of <i>tert</i>‐Butyllithium by the Addition of Stoichiometric Amounts of Tetrahydrofuran
  作者：Johannes Kleinheider、Tobias Schrimpf、Rebecca Scheel、Tristan Mairath、Andreas Hermann、Kathrin Knepper、Carsten Strohmann

  DOI：10.1002/chem.202304226

  日期：2024.3.15

  In alkyllithium chemistry the highest reactivity has historically been linked to the smallest degree of aggregation possible. Since tert‐butyllithium is known to form a monomer in tetrahydrofuran solution, using just stoichiometric amounts of the lewis base to selectively form a dimeric species seemed irrational. In this study, we showed a considerable increase of the reactivity of t‐BuLi when using stoichiometric amounts of THF in the non‐polar solvent n‐pentane in order to enable the deprotonation of simple methyl silanes and other low C−H−acidic substrates. In this context, we were able to obtain the corresponding aggregates of t‐BuLi with the ligand THF in suspension and as crystalline solids and investigate them by single crystal X‐ray structural analysis, in situ FTIR spectroscopy and quantum chemical calculations. Furthermore, we were able to explain the enhanced reactivity of t‐BuLi with stoichiometric amounts of THF on the basis of structural features of the bridged dimer obtained under these conditions. With these findings, we present a new target in the aggregation of alkyllithium reagents: the selectively formed “frustrated” aggregates!

  摘要在烷基锂化学中，最高的反应活性历来与尽可能小的聚集程度有关。由于叔丁基锂在四氢呋喃溶液中形成单体是已知的，因此仅使用一定量的路易斯碱来选择性地形成二聚物似乎是不合理的。在这项研究中，我们发现当在非极性溶剂正戊烷中使用等量的四氢呋喃时，t-BuLi 的反应活性大大提高，从而能够对简单的甲基硅烷和其他低 C-H 酸性底物进行去质子化反应。在这种情况下，我们获得了 t-BuLi 与配体 THF 在悬浮液中的相应聚集体和结晶固体，并通过单晶 X 射线结构分析、原位傅立叶变换红外光谱和量子化学计算对其进行了研究。此外，我们还根据在这些条件下获得的桥联二聚体的结构特征，解释了 t-BuLi 与等量 THF 反应性增强的原因。通过这些发现，我们提出了烷基锂试剂聚集的一个新目标：选择性形成的 "受挫 "聚集体！
• Sulfamyl Radicals Direct Photoredox-Mediated Giese Reactions at Unactivated C(3)–H Bonds
  作者：Anastasia L. G. Kanegusuku、Thomas Castanheiro、Suraj K. Ayer、Jennifer L. Roizen

  DOI：10.1021/acs.orglett.9b02234

  日期：2019.8.2

  Alcohol-anchored sulfamate esters guide the alkylation of tertiary and secondary aliphatic C(3)-H bonds. The transformation proceeds directly from N-H bonds with a catalytic oxidant, a contrast to prior methods which have required preoxidation of the reactive nitrogen center, or employed stoichiometric amounts of strong oxidants to obtain the sulfamyl radical. These sulfamyl radicals template otherwise rare 1,6-hydrogen-atom transfer (HAT) processes via seven-membered ring transition states to enable C(3)-H functionalization during Giese reactions.
• Pola,J. et al., Collection of Czechoslovak Chemical Communications, 1974, vol. 39, p. 3705 - 3710
  作者：Pola,J. et al.

  DOI：——

  日期：——
• Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model
  作者：Philip J. Rybczynski、Roxanne E. Zeck、Joseph Dudash、Donald W. Combs、Thomas P. Burris、Maria Yang、Melville C. Osborne、Xiaoli Chen、Keith T. Demarest

  DOI：10.1021/jm0301888

  日期：2004.1.1

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.