tert-butyl(dodec-11-ynyloxy)dimethylsilane | 128098-41-9

• 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: tert-butyl(dodec-11-ynyloxy)dimethylsilane
• 英文别名: 1-t-Butyldimethylsilyloxydodec-11-yne；tert-butyl-dodec-11-ynoxy-dimethylsilane
• CAS: 128098-41-9
• 化学式: C₁₈H₃₆OSi
• 分子量: 296.569
• InChiKey: AUHQKCUUUPUCSS-UHFFFAOYSA-N

物化性质

• 沸点：
  326.9±15.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  tert-butyl(dodec-11-ynyloxy)dimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 methyl 4-(12-((tert-butyldimethylsilyl)oxy)dodecyl)-3,5-dimethoxybenzoate
  参考文献：
  名称：

  Dual bioactivity of resveratrol fatty alcohols: Differentiation of neural stem cells and modulation of neuroinflammation

  摘要：

  The synthesis of resveratrol fatty alcohols (RFAs), a new class of small molecules presenting strong potential for the treatment of neurological diseases, is described. RFAs, hybrid compounds combining the resveratrol nucleus and (omega-alkanol side chains, are able to modulate neuroinflammation and to induce differentiation of neural stem cells into mature neurons. Acting on neuroprotection and neuroregeneration, RFAs represent an innovative approach for the treatment or cure of neuropathies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.037
• 作为产物：
  描述：

  1-tetrahydropyranyloxy-n-2-dodecyn 在 咪唑 、 potassium tert-butylate 、 lithium 、 对甲苯磺酸 、 1,2-丙二胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 tert-butyl(dodec-11-ynyloxy)dimethylsilane
  参考文献：
  名称：

  通过全合成阐明花环产乙酸原（+）-蒙特克里斯汀的立体结构

  摘要：

  完成了ent -5- epi- montecristin（1a）和（-）-montecristin（1b）的总合成。化合物1a和1b的立体中心是通过反式构型的β，γ-不饱和酯6的不对称二羟基化而建立的（→ 4，至多80％ee；方案3；改进的程序，至多94％ee：方案7）和56（→ 55，97％ee的：方案9），而立体ç C键从carbocuprations干48 → 49和50 → 51（方案9）。用PPh 3和DEAD处理羟基内酯27（方案7）， 3a（方案12）和3b（方案13），我们发现无外消旋的脱水作用生成丁烯内酯26，无差向异构化的脱水作用生成丁烯内酯2a和2b 。有关的[ α ] d合成的值 1A和1B到[ α ] d天然（+）的值- montecristin，测定其侧链立体中心的绝对构型为[R 。

  DOI：

  10.1039/b002905j

文献信息

• Synthesis of E-vinyl iodides via Pd-catalyzed hydrostannation of terminal alkynes
  作者：Alla Darwish、J. Michael Chong

  DOI：10.1016/j.tet.2011.10.104

  日期：2012.1

  E-Vinyl iodides may be prepared via a one-pot reaction involving Pd-catalyzed hydrostannation of terminal alkynes followed by iodinolysis of the intermediate vinylstannane. The synthesis is tolerant of functional groups, such as alcohols and esters.

  E-乙烯基碘化物可通过一锅反应制备，该反应包括钯催化末端炔烃的氢化锡锡烷化反应，然后对中间乙烯基锡烷进行碘解。该合成耐受官能团，例如醇和酯。
• Activity-Based Proteome Profiling of Potential Cellular Targets of Orlistat − An FDA-Approved Drug with Anti-Tumor Activities
  作者：Peng-Yu Yang、Kai Liu、Mun Hong Ngai、Martin J. Lear、Markus R. Wenk、Shao Q. Yao

  DOI：10.1021/ja907716f

  日期：2010.1.20

  Orlistat, or tetrahydrolipstatin (THL), is an FDA-approved antiobesity drug with potential antitumor activities. Cellular off-targets and potential side effects of Orlistat in cancer therapies, however, have not been extensively explored thus far. In this study, we report the total of synthesis of THL-like protein-reactive probes, in which extremely conservative modifications (i.e., an alkyne handle) were introduced in the parental THL structure to maintain the native biological properties of Orlistat, while providing the necessary functionality for target identification via the bio-orthogonal click chemistry. With these natural productlike, cell-permeable probes, we were able to demonstrate, for the first time, this chemical proteomic approach is suitable for the identification of previously unknown cellular targets of Orlistat. In addition to the expected fatty acid synthase (FAS), we identified a total of eight new targets, some of which were further validated by experiments including Western blotting, recombinant protein expression, and site-directed mutagenesis. Our findings have important implications in the consideration of Orlistat as a potential anticancer drug at its early stages of development for cancer therapy. Our strategy should be broadly useful for off-target identification against quite a number of existing drugs and/or candidates, which are also covalent modifiers of their biological targets.