tert-butyl(oxiran-2-ylmethoxy)diphenylsilane | 194805-72-6

• 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(oxiran-2-ylmethoxy)diphenylsilane
• 英文别名: tert-butyl-(oxiran-2-ylmethoxy)-diphenylsilane
• CAS: 194805-72-6
• 化学式: C₁₉H₂₄O₂Si
• 分子量: 312.484
• InChiKey: OFXJIOVCMVBKRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.3±24.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl(oxiran-2-ylmethoxy)diphenylsilane 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel steroid-modified ether phospholipids

  摘要：

  Platelet activating factor is one of the most potent inflammatory ether phospholipid mediators known and structurally modified analogues are of considerable interest as potential therapeutic preparations. Inspired by the proposed structure for a novel endogenous hydroxy-PAF analogue isolated recently from gingival crevicular fluid, we designed and prepared two novel steroid-modified ether phospholipids. These two novel compounds exhibit marked chemical and biological similarities to their endogenous prototype and they antagonize it being less active in inducing washed platelet aggregation through PAF receptors. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.07.007
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyloxy)prop-1-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以5.37 g的产率得到tert-butyl(oxiran-2-ylmethoxy)diphenylsilane
  参考文献：
  名称：

  Hexafluoroisopropanol as a Unique Solvent for Stereoselective Iododesilylation of Vinylsilanes

  摘要：

  Stereoselective preparation of iodoalkenes from vinylsilanes is described. 1,1,1,3,3,3-HexafluoroisopropanoI serves as a unique solvent that ensures high yields and stereoselectivities in the lododesilylation of a variety of functionalized substrates.

  DOI：

  10.1021/ol800341z

文献信息

• Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach
  作者：Jingjing Wang、Samuel Z Y Ting、Joanne E Harvey

  DOI：10.3762/bjoc.11.197

  日期：——

  Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achieved through the coupling of Bestmann ylide, an alcohol and an α,β-unsaturated aldehyde. Primary and secondary alcohols, including allylic alcohols, are suitable substrates; the newly formed alkene has an E-geometry. Strategically, this represents a highly efficient route to unsaturated polyketide derivatives. A linchpin approach to the synthesis of a major fragment of the natural products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment.

  Bestmann亚磷酰基[(三苯基磷氧基)酮烯]作为一种化学枢纽，将亲核实体，如醇或胺，与羰基部分连接起来，分别生成不饱和酯和酰胺。在这项工作中，通过Bestmann亚磷酰基、醇和α,β-不饱和醛的偶联实现了α,β,γ,δ-不饱和酯(二烯酸酯)的生成。一级和二级醇，包括烯丙基醇，都是合适的底物；新形成烯烃具有E-型几何结构。策略上，这代表了一条高效合成不饱和聚酮衍生物的路线。利用Bestmann亚磷酰基将C16-C20醇与C3-C8醛片段连接起来，研究了通过枢纽法合成天然产物zampanolide和dactylolide主要片段的方法。
• Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional<i>syn</i>-1,3-Diol Derivatives
  作者：Dean Holt、Matthew J. Gaunt

  DOI：10.1002/anie.201501995

  日期：2015.6.26

  functionalized 1,3‐diol derivatives is reported. Employing a copper‐catalyzed oxy‐alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn‐1,3‐carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide‐like

  报道了一种新型的合成多种功能化的1,3-二醇衍生物的方法。采用铜催化的氧-烯基化策略，一系列易于获得的取代的均烯丙基醇衍生物和烯基（芳基）碘鎓盐以优异的收率和高选择性结合形成顺式1,3-碳酸酯。此外，所形成的产物适合重复的反应序列，从而提供了高度复杂的聚酮化合物样片段。
• A Modified Synthesis of Oxetan-3-ol
  作者：X. Y. Xia、W. Sun、W. He、Y. Feng、L. Zhan、Y. Luo

  DOI：10.1134/s107042802005022x

  日期：2020.5

  of terminal epoxides with 2-bromobenzoic acid catalyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in a good yield.

  摘要在四丁基溴化铵的催化下，完成了末端环氧化物与2-溴苯甲酸的高度区域选择性开环反应。该程序操作简单且实用，可用于合成一系列β-羟基酯。使用该方案，可以高效且高收率地制备环氧乙烷-3-醇。
• Catalytic synthesis of enantiopure mixed diacylglycerols – synthesis of a major M. tuberculosis phospholipid and platelet activating factor
  作者：Peter Fodran、Adriaan J. Minnaard

  DOI：10.1039/c3ob41483c

  日期：——

  An efficient catalytic one-pot synthesis of TBDMS-protected diacylglycerols has been developed, starting from enantiopure glycidol. Subsequent migration-free deprotection leads to stereo- and regiochemically pure diacylglycerols. This novel strategy has been applied to the synthesis of a major Mycobacterium tuberculosis phospholipid, its desmethyl analogue, and platelet activating factor.

  一种高效催化的一锅法合成TBDMS保护的二酰基甘油已被开发出来，从手性纯甘油酸环丙烷开始，随后无迁移的脱保护步骤产生立体化学和区域化学纯的二酰基甘油。这种新颖的策略已应用于合成主要的结核分枝杆菌磷脂、其脱甲基类似物和血小板活化因子。
• Unveiling Latent α-Iminocarbene Reactivity for Intermolecular Cascade Reactions through Alkyne Oxidative Amination
  作者：Nina Mace、Aaron R. Thornton、Simon B. Blakey

  DOI：10.1002/anie.201301087

  日期：2013.5.27

  Setting a trap: Described is the development of a metallonitrene‐initiated alkyne oxidation cascade with intermolecular trapping of the reactive intermediate with a variety of allyl ethers to provide α‐oxyimine products in which new CN, CO, and CC bonds have all been generated (see Scheme; tfacam=trifluoroacetamide).

  设置陷阱：描述的是与反应性中间体的分子间俘获一个metallonitrene发起炔氧化级联的发展与各种烯丙基醚，以提供α-oxyimine产品，其中新CN，C  O，和C  Ç所有键均已生成（请参阅方案； tfacam =三氟乙酰胺）。