1,10-decanediol dimethyl ether | 53759-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,10-decanediol dimethyl ether
• 英文别名: 1,10-dimethoxydecane；Dimethoxydecan；1,10-Dimethoxy-decan
• CAS: 53759-62-9
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: JHGQQGJRIPMMEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,10-decanediol dimethyl ether 、 碘甲烷 在 六氟磷酸银 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 Decamethoxoniumion
  参考文献：
  名称：

  Decamethoxonium, an alkylating analog of decamethonium

  摘要：

  DOI：

  10.1021/ja00831a051
• 作为产物：
  描述：

  1,10-癸二醇 在 吡啶 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 1,10-decanediol dimethyl ether
  参考文献：
  名称：

  Fingerprinting a transition-structure guest by a building-block approach with an incremental series of catalytic hosts. Structural requirements for glyme and .alpha.,.omega.-dimethoxyalkane catalyses in N-methylbutylaminolysis and butylaminolysis of 4-nitrophenyl acetate in chlorobenzene

  摘要：

  Glymes, H-(CH2OCH2)n-H, GLM(n), catalyze butylaminolysis of 4-nitrophenyl acetate in chlorobenzene. Values of k(cat)/Oxy, where Oxy is the number of oxygens in the catalyst, increase with oligomer length up to triglyme, GLM(4), and then plateau. Optimal catalysis on a per oxygen basis requires a -(CH2OCH2)4-fragment, which suggests a four-point recognition of the secondary ammonium ion of the zwitterionic tetrahedral intermediate (TI) (J. Org. Chem. 1991, 56, 2821-2826). Dissection of individual structural components and reassembly to the same structure of the complex verifies this model. The following kinetic studies of 4-nitrophenyl acetate in chlorobenzene have accomplished the task: (a) methylbutylaminolysis catalyzed by GLM(n), n = 2-4; (b) methylbutylaminolysis catalyzed by alpha,omega-dimethoxyalkanes, CH3O-(CH2)n-OCH3, DME(n), n = 2-10 and 12; and (c) butylaminolysis catalyzed by DME(n), n = 2-10 and 12. Experiment a has revealed that k(cat)/Oxy is the same for GLM(2)-GLM(4). Optimal catalysis for breakdown of a zwitterionic TI with one ammonium proton only requires a -(CH2OCH2)2- fragment. Experiment b has shown that k(cat)/Oxy is largest for DME(2) with the values for the remaining DMEs 2-2.5-fold lower. A -CH2CH2- is the best spacer between the two oxygens. Thus, bifurcated hydrogen-bond formation between the two oxygens and the one ammonium proton enhances catalysis. Experiment c has revealed that k(cat)/Oxy for DME(2) exceeds the remaining DMEs by 3-3.6-fold, except for DME(8) and DME(10), which have values of k(cat)/Oxy only 1.7-fold slower. DME(8), the carba analogue of GLM(4), likely binds to the two ammonium protons individually with the two oxygens. DME(10) behaves similarly. GLM(4) catalysis of butylaminolysis identifies -(CH2OCH2)4- as an optimal size. DME(8) catalysis confirms this size, although the two catalysts stabilize the two-proton ammonium ion differently. GLM(4) catalyzes butylaminolysis by forming two bifurcated hydrogen bonds. This suggested structure defines the size of the ammonium ion, which agrees with X-ray structural studies of polyether-ammonium complexes. Mechanistic proposals of butylaminolysis of aryl esters require such an ion. The results of this study confirm the structure of the ion in the rate-limiting step. This building-block approach is a method for ''fingerprinting'' ammonium ions in transition structures of ionogenic reactions.

  DOI：

  10.1021/jo00027a014

文献信息

• Methylation of Alcohols, Phenols, and Carboxylic Acids, and Selective Monomethylation of Diols and Dicarboxylic Acids with Dimethyl Sulfate by Use of Alumina
  作者：Haruo Ogawa、Youko Ichimura、Teiji Chihara、Shousuke Teratani、Kazuo Taya

  DOI：10.1246/bcsj.59.2481

  日期：1986.8

  Alcohols in cyclohexane give their methyl ethers in high yields by the use of a combination of dimethyl sulfate and alumina. Some diols and dicarboxylic acids adsorbed on alumina react with dimethyl sulfate and produce the corresponding monomethyl ethers and esters in high selectivities.

  通过使用硫酸二甲酯和氧化铝的组合，环己烷中的醇以高产率得到它们的甲基醚。一些吸附在氧化铝上的二醇和二元羧酸与硫酸二甲酯反应并以高选择性生成相应的单甲醚和酯。
• Ruthenium-Catalyzed Selective Hydro<i>boronolysis</i> of Ethers
  作者：Akash Kaithal、Deepti Kalsi、Varadhan Krishnakumar、Sandip Pattanaik、Alexis Bordet、Walter Leitner、Chidambaram Gunanathan

  DOI：10.1021/acscatal.0c04269

  日期：2020.12.18

  the formation of alkylboronate esters and methane. Cyclic ethers are also amenable to catalytic hydroboronolysis. Mechanistic studies indicated the immediate in situ formation of a mono-hydridobridged dinuclear ruthenium complex [(η6-p-cymene)RuCl}2(μ–H−μ–Cl)] (2), which is highly active for hydroboronolysis of ethers. Over time, the dinuclear species decompose to produce ruthenium nanoparticles that

  HBpin的钌催化反应与取代有机醚导致的C-O键的激活，导致通过加氢形成烷烃和硼酸酯的boronolysis。使用钌预催化剂[Ru（对-cymene）Cl] 2 Cl 2（1），反应在135°C和大气压（135°C时约1.5 bar）的纯净条件下进行。不对称的二苄基醚在电子相对较差的C-O键上进行选择性氢硼水解。在芳基苄基或烷基苄基醚中，C O键裂解选择性地发生在C Bn -OR键上（Bn =苄基）；在烷基甲基醚中，C Me的选择性解构-OR键导致形成烷基硼酸酯和甲烷。环醚也适合催化氢硼水解。机制研究表明在单hydridobridged双核钌络合物原位形成立即[（η 6 - p -cymene）的RuCl} 2（μ-H-μ-Cl）的（2），它是高活性的用于水力boronolysis醚。随着时间的流逝，双核物质分解产生钌纳米颗粒，该钌纳米颗粒也对该转化具有活性。使用这种催化系统，氢硼分解
• Lenne,H.-U. et al., Justus Liebigs Annalen der Chemie, 1970, vol. 732, p. 70 - 96
  作者：Lenne,H.-U. et al.

  DOI：——

  日期：——
• Epsztein, Bulletin de la Societe Chimique de France, 1956, p. 158
  作者：Epsztein

  DOI：——

  日期：——
• Paul; Riobe, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1950, vol. 230, p. 1185
  作者：Paul、Riobe

  DOI：——

  日期：——