11-(t-butyldimethylsiloxy)-2-undecanone | 93131-84-1

• 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: 11-(t-butyldimethylsiloxy)-2-undecanone
• 英文别名: 1-tert-Butyldimethylsilyloxy-10-undecanone；11-[(tert-butyldimethylsilyl)oxy]undecan-2-one；11-[Tert-butyl(dimethyl)silyl]oxyundecan-2-one
• CAS: 93131-84-1
• 化学式: C₁₇H₃₆O₂Si
• 分子量: 300.557
• InChiKey: DRBDSIZPQBOTIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  11-(t-butyldimethylsiloxy)-2-undecanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-羟基-10-十一烷酮
  参考文献：
  名称：

  用于醇选择性氧化的氟铬酸吡啶鎓或氯铬酸苄基三甲基铵

  摘要：

  在伯醇存在下仲醇的选择性氧化已通过以下顺序实现，(1) 用 t-BuMe2SiCl 选择性保护伯醇，(2) 用标题试剂氧化仲醇，以及 (3) 伯醇的脱保护羟基。

  DOI：

  10.1246/bcsj.57.2019
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 11-(t-butyldimethylsiloxy)-2-undecanone
  参考文献：
  名称：

  用于醇选择性氧化的氟铬酸吡啶鎓或氯铬酸苄基三甲基铵

  摘要：

  在伯醇存在下仲醇的选择性氧化已通过以下顺序实现，(1) 用 t-BuMe2SiCl 选择性保护伯醇，(2) 用标题试剂氧化仲醇，以及 (3) 伯醇的脱保护羟基。

  DOI：

  10.1246/bcsj.57.2019

文献信息

• Hydration of Terminal Alkynes Catalyzed by Water-Soluble Cobalt Porphyrin Complexes
  作者：Tadashi Tachinami、Takuho Nishimura、Richiro Ushimaru、Ryoji Noyori、Hiroshi Naka

  DOI：10.1021/ja310282t

  日期：2013.1.9

  Water-soluble cobalt(III) porphyrin complexes were found to promote the hydration of terminal alkynes to give methyl ketones. The alkyne hydration proceeded in good to excellent yield with 0.1 to 2 mol % cobalt catalyst 1 and was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters;

  发现水溶性钴 (III) 卟啉配合物可促进末端炔烃的水合生成甲基酮。炔烃水合在 0.1 至 2 mol% 的钴催化剂 1 下以良好的产率进行，并且与酸/碱或氧化还原敏感官能团（如烷基甲硅烷基醚）的存在相容；烯丙基醚；三苯醚；苄基醚；羧酸酯；硼酸酯；甲酰胺；腈类；和硝基、碘和缩醛基团。这里测试的一些炔烃底物很难水合。炔烃水合可以以克规模进行，催化剂可以通过水后处理回收。
• Sustainable Radical Reduction through Catalytic Hydrogen Atom Transfer
  作者：Andreas Gansäuer、Chun-An Fan、Frederik Piestert

  DOI：10.1021/ja801232t

  日期：2008.6.1

  A system with coupled catalytic cycles is described that allows radical reduction by hydrogen atom abstraction from rhodium hydrides. These intermediates are generated from H2 activation by Wilkinson's catalyst. Radical generation is carried out by titanocene-catalyzed electron transfer to epoxides.

  描述了一种具有耦合催化循环的系统，该系统允许通过从氢化铑中提取氢原子来进行自由基还原。这些中间体是由威尔金森催化剂的 H2 活化产生的。自由基生成是通过二茂钛催化的电子转移到环氧化物来进行的。
• Coupling Titanium and Chromium Catalysis in a Reaction Network for the Reprogramming of [BH₄]⁻ as Electron Transfer and Hydrogen Atom Transfer Reagent for Radical Chemistry
  作者：Michael Heinz、Gregor Weiss、Grigoriy Shizgal、Anastasia Panfilova、Andreas Gansäuer

  DOI：10.1002/anie.202308680

  日期：2023.9.18

  Reprogramming the typical hydride character of borohydrides to a stepwise electron and H-atom transfer reagent allows epoxide reduction, C−C bond formation and regiodivergent epoxide opening in an unusual manner by avoiding SN2-type reactivity of [BH4]−. The readily available Li[BH4] is used as sole stoichiometric reagent.

  通过有效耦合地球上储量丰富的两种金属钛和铬，从催化循环到催化球。将硼氢化物的典型氢化物特征重新编程为逐步电子和氢原子转移试剂，通过避免 [BH 4 ] -的 S N 2 型反应性，可以以不寻常的方式进行环氧化物还原、CC 键形成和区域发散环氧化物打开。容易获得的Li[BH 4 ]被用作唯一的化学计量试剂。
• NONAKA, TSUYOSHI;KANEMOTO, SHIGEKAZU;OSHIMA, KOICHIRO;NOZAKI, HITOSI, BULL. CHEM. SOC. JAP., 1984, 57, N 7, 2019-2020
  作者：NONAKA, TSUYOSHI、KANEMOTO, SHIGEKAZU、OSHIMA, KOICHIRO、NOZAKI, HITOSI

  DOI：——

  日期：——
• Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella
  作者：Regine Gries、Gerhard Gries、G. G. Skip King、Chris T. Maier

  DOI：10.1023/b:joec.0000006390.43868.3b

  日期：1997.4

  Three methylated hydrocarbons, 10,14-dimethyloctadec-1-ene (10Me14Me-1-ene-18Hy = 5Me9Me-17-ene-18Hy), 5,9-dimethyloctadecane (5Me9Me-18Hy), and 5,9-dimethylheptadecane (5Me9Me-17Hy), are synergistic sex pheromone components of the leafminer Lyonetia prunifoliella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic detection (GC-EAD), and one compound, 10Me14Me-1-ene-18Hy also by coupled GC-mass spectrometry. In field trapping experiments, 10Me14Me-1-ene-18Hy 5Me9Me-18Hy, and 5Me9Me-17Hy singly were unattractive to males but in ternary combination attracted numerous male moths. Attractiveness of the three-component blend significantly exceeded that of two-component blends. No attraction of males to pheromone lures without 10Me14Me-1-ene-18Hy indicates that this compound is essential for pheromone communication of L. prunifoliella. Common C-5 and C-9 methyl branches in lyonetiid pheromone hydrocarbons suggest a common biosynthetic pathway; the presence of 5Me9Me-17Hy and 5Me9Me-18Hy in pheromone blends of L. prunifoliella and Leucoptera malifoliella provides evidence for phylogeny of lyonetiid chemical communication. Determination of the stereoisomeric composition is required to completely describe the pheromone blend of L. prunifoliella and to support the hypothesis of phylogenetically related sex pheromones.