6-((tert-butyldimethylsilyl)oxy)hexan-2-one | 110862-03-8

• 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: 6-((tert-butyldimethylsilyl)oxy)hexan-2-one
• 英文别名: 2-Hexanone, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-；6-[tert-butyl(dimethyl)silyl]oxyhexan-2-one
• CAS: 110862-03-8
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: YUFRIBDLMRZBAB-UHFFFAOYSA-N

物化性质

• 沸点：
  271.4±23.0 °C(Predicted)
• 密度：
  0.866±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-((tert-butyldimethylsilyl)oxy)hexan-2-one 在 四氧化锇 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 14.83h， 生成
  参考文献：
  名称：

  Concise Synthesis of the C15–C38 Fragment of Okadaic Acid: Application of the Suzuki–Miyaura Reaction to Spiroacetal Synthesis

  摘要：

  A concise synthetic entry to the C15-C38 fragment of okadaic acid by exploiting a Suzuki-Miyaura reaction for the rapid assembly of the spiroacetal substructures has been developed. The present synthesis was completed in 19 linear steps from a commercially available material, showcasing the efficiency of our synthetic strategy.

  DOI：

  10.1021/ol503491t
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 吗啉 、 Au-TiO₂ 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以95%的产率得到6-((tert-butyldimethylsilyl)oxy)hexan-2-one
  参考文献：
  名称：

  Supported Gold Nanoparticle-Catalyzed Hydration of Alkynes under Basic Conditions

  摘要：

  TiO2-supported nanosize gold particles catalyze the hydration of alkynes using morpholine as a basic cocatalyst. Unlike most homogeneous cationic gold catalysts, the TiO2-Au/morpholine system is weakly basic and is compatible with acid-sensitive functional groups (e.g., silyl ethers, ketals) or with a strongly coordinating group such as pyridine. Whats more, this gold catalyst can be recycled by simple filtration and works well in flow reactors.

  DOI：

  10.1021/ol5033859

文献信息

• Diastereoselective Oxidative CN/CO and CN/CN Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused<i>N</i>-Arylindolines
  作者：Scott A. Morris、Theresa H. Nguyen、Nan Zheng

  DOI：10.1002/adsc.201500317

  日期：2015.7.6

  The synthesis of fused N‐arylindolines using visible light photoredox catalysis has been developed. We previously described that photogenerated amine radical cations generate substituted indoles through an intermediate benzylic carbocation. Herein, we expand the application of this chemistry by trapping the benzylic carbocation with tethered heteronucleophiles. The reactivity of the photogenerated

  已经开发出了利用可见光光氧化还原催化合成稠合N-芳基二氮杂环林的方法。我们以前曾描述过，光生胺自由基阳离子通过中间的苄基碳正离子生成取代的吲哚。在本文中，我们通过用束缚的异亲核试剂捕获苄基碳正离子来扩展该化学方法的应用。探索了光生苄基碳正离子的反应性，并将其应用于具有各种电子特性和环约束的一系列底物。所描述的方法以中等至良好的收率提供了带有四取代碳立体中心且具有大于99：1非对映选择性的C-2和C-3熔融二氢吲哚。
• Wacker oxidation of terminal olefins in a mixture of [bmim][BF4] and water
  作者：I.A. Ansari、Sipak Joyasawal、Manoj K. Gupta、J.S. Yadav、R. Gree

  DOI：10.1016/j.tetlet.2005.09.013

  日期：2005.10

  simple and efficient PdCl2/CuCl catalyzed oxidation of alkenes has been successfully developed using a mixture of water and the ionic liquid [bmim][BF4] as solvent. Starting from various types of terminal olefins, the corresponding ketones have been prepared under mild reaction conditions and obtained in good to excellent yields after a simple extraction with diethyl ether. Furthermore, it was possible to

  使用水和离子液体[bmim] [BF 4 ]的混合物作为溶剂，已经成功开发了一种简单有效的PdCl 2 / CuCl催化的烯烃氧化方法。由各种类型的末端烯烃开始，已在温和的反应条件下制备了相应的酮，并在用二乙醚简单萃取后以良好或优异的收率得到了相应的酮。此外，可以回收和再利用离子液体和催化体系。
• A Novel Method for Direct Construction of Indole Skeletons by Intramolecular Carbopalladation of Allenes Followed by Nucleophilic Substitution
  作者：Kunio Hiroi、Yuko Hiratsuka、Kazuhiro Watanabe、Ikuko Abe、Fumiko Kato、Mayumi Hiroi

  DOI：10.1055/s-2001-10787

  日期：——

  Upon treatment with a palladium catalyst, (o-iodoanilinoalkyl)allene compounds undergo intramolecular carbopalladation of allenes followed by intramolecular amination of π-allylpalladium complexes to afford indole derivatives in fairly good yields.

  在钯催化剂的作用下，(邻碘苯胺基烷基)丙二烯化合物经历丙二烯的分子内碳钯化反应，随后发生π-烯丙基钯配合物的分子内胺化反应，从而以相当好的产率得到吲哚衍生物。
• Galantamine-Curcumin Hybrids as Dual-Site Binding Acetylcholinesterase Inhibitors
  作者：Georgi Stavrakov、Irena Philipova、Atanas Lukarski、Mariyana Atanasova、Dimitrina Zheleva、Zvetanka D. Zhivkova、Stefan Ivanov、Teodora Atanasova、Spiro Konstantinov、Irini Doytchinova

  DOI：10.3390/molecules25153341

  日期：——

  Galantamine (GAL) and curcumin (CU) are alkaloids used to improve symptomatically neurodegenerative conditions like Alzheimer’s disease (AD). GAL acts mainly as an inhibitor of the enzyme acetylcholinesterase (AChE). CU binds to amyloid-beta (Aβ) oligomers and inhibits the formation of Aβ plaques. Here, we combine GAL core with CU fragments and design a combinatorial library of GAL-CU hybrids as dual-site binding AChE inhibitors. The designed hybrids are screened for optimal ADME properties and BBB permeability and docked on AChE. The 14 best performing compounds are synthesized and tested in vitro for neurotoxicity and anti-AChE activity. Five of them are less toxic than GAL and CU and show activities between 41 and 186 times higher than GAL.

  盖兰他敏（GAL）和姜黄素（CU）是用来改善像阿尔茨海默病（AD）这样的神经退行性疾病症状的生物碱。GAL主要作为乙酰胆碱酯酶（AChE）的抑制剂。CU结合到淀粉样蛋白β（Aβ）寡聚体并抑制Aβ斑块的形成。在这里，我们将GAL的核心与CU的片段结合，设计了一个GAL-CU杂交物的组合库，作为双位结合AChE抑制剂。设计的杂交物被筛选出具有最佳的ADME性能和血脑屏障透过性，并在AChE上进行对接。表现最佳的14种化合物被合成并在体外进行神经毒性和抗AChE活性测试。其中五种化合物比GAL和CU更少毒，并且显示出比GAL高41到186倍的活性。
• Asymmetric Dehydrative Cyclization of ω-Hydroxy Allyl Alcohols Catalyzed by Ruthenium Complexes
  作者：Shinji Tanaka、Tomoaki Seki、Masato Kitamura

  DOI：10.1002/anie.200904671

  日期：2009.11.9

  New axially chiral ligands and their allyl esters have been designed and synthesized. The combination of these ligands with [CpRu(CH3CN)3]PF6 has realized highly efficient intramolecular dehydrative cylization of ω‐hydroxy allyl alcohols, to give α‐alkenyl‐substituted cyclic ethers with up to greater than 99:1 enantiomeric ratio without activation of the allylic moieties (see scheme; Cp=cyclopentadienyl

  已经设计并合成了新的轴向手性配体及其烯丙基酯。这些配体与[CpRu（CH 3 CN）3 ] PF 6的结合实现了ω-羟基烯丙醇的高效分子内脱水环化反应，得到对映体比高达99：1的α-烯基取代的环状醚没有活化烯丙基部分（参见方案； Cp ＝环戊二烯基，naph ＝萘基，py ＝吡啶）。