undecyl undecanoate | 42231-61-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undecyl undecanoate
• CAS: 42231-61-8
• 化学式: C₂₂H₄₄O₂
• 分子量: 340.59
• InChiKey: BNJRHNHQYFVXTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  24
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十一烷醇 在 sodium bromate 、 硫酸 、 sodium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 以99%的产率得到undecyl undecanoate
  参考文献：
  名称：

  伯醇在室温下在水性介质中的氧化酯化

  摘要：

  摘要 脂肪族伯醇与溴化物和溴酸盐对在室温下在水性酸性介质中的氧化酯化反应具有广泛的脂肪族和环状醇底物范围，并获得了优异的产品收率。图形概要

  DOI：

  10.1080/00397911.2018.1458320

文献信息

• The Oxidation of Alcohols in<i>N</i>-Oxyl-Immobilized Silica Gel/Aqueous NaOCl Disperse Systems. A Prominent Access to a Column-Flow System
  作者：Hideo Tanaka、Jingyu Chou、Machiko Mine、Manabu Kuroboshi

  DOI：10.1246/bcsj.77.1745

  日期：2004.9

  The oxidation of alcohols was performed successfully in a disperse system with N-oxyl-adsorbed or immobilized silica gel as a disperse phase and aqueous NaOCl as a disperse medium. In the disperse system, the oxidation of sec-alcohols afforded the corresponding ketones, while prim-alcohols were oxidized to aldehydes and/or carboxylic acids depending on their structures and reaction conditions. The N-oxyl-immobilized silica gel was recovered and repeatedly used without a significant change in the product yields. A column-flow system was also investigated for the oxidation of alcohols by use of a newly devised column packed with the N-oxyl-immobilized silica gel.

  在分散体系中，以N-氧杂-吸附或固定化硅胶为分散相，以水合NaOCl为分散介质，成功地进行了醇的氧化反应。在分散体系中，二级醇被氧化成相应的酮，而一级醇则根据其结构和反应条件的不同被氧化成醛和/或羧酸。N-氧杂固定化硅胶可被回收并在不显著影响产物收率的情况下重复使用。还研究了一种新的柱流系统，该系统采用新设计的填充N-氧杂固定化硅胶的柱子来进行醇的氧化反应。
• Oxidation of Diols and Ethers by NaBrO₃/NaHSO₃Reagent
  作者：Satoshi Sakaguchi、Daisuke Kikuchi、Yasutaka Ishii

  DOI：10.1246/bcsj.70.2561

  日期：1997.10

  NaBrO3 combined with NaHSO3 was found to be an excellent oxidizing reagent of alcohols, diols, and ethers under mild conditions. A variety of aliphatic and cyclic diols were selectively oxidized with satisfactory yields to the corresponding hydroxy ketones and/or diketones, which are difficult to selectively prepare due to a concomitant formation of cleaved products. For example, 2-hydroxycyclohexanone and 1,2-cyclohexanedione were selectively formed by allowing 1,2-cyclohexanediol to react with NaBrO3/NaHSO3 reagent in a selected solvent. On the other hand, an alkyl ether, such as dioctyl ether, reacted with NaBrO3/NaHSO3 in water at room temperature to give octyl octanoate in 82% yield. The same oxidation at higher temperature (60 °C) produced the α-brominated ester, octyl 2-bromooctanoate, which is considered to be formed through an alkenyl alkyl ether as the intermediate. The treatment of 1-ethoxy-1-heptene with NaBrO3/NaHSO3 afforded ethyl 2-bromoheptanoate and 2-bromoheptanoic acid as the major products.

  NaBrO3与NaHSO3组合被发现是一种在温和条件下对醇、二醇和醚类具有优异氧化能力的试剂。多种脂肪族和环状二醇被选择性地氧化为相应的羟基酮和/或二酮，产率令人满意，这些产物由于伴随生成断裂产物而难以选择性制备。例如，通过在选定溶剂中使1,2-环己二醇与NaBrO3/NaHSO3试剂反应，选择性地生成了2-羟基环己酮和1,2-环己二酮。另一方面，在室温下，二辛醚在水中的NaBrO3/NaHSO3反应以82%的产率得到了辛基辛酸酯。同样的氧化反应在较高温度（60°C）下产生了α-溴代酯，即辛基2-溴辛酸酯，这被认为是通过烯基烷基醚作为中间体形成的。使用NaBrO3/NaHSO3处理1-乙氧基-1-庚烯，主要产物是乙基2-溴庚酸酯和2-溴庚酸。
• Modified Markó’s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature
  作者：Takeshi Nishii、Tomomi Ouchi、Aya Matsuda、Yuka Matsubara、Yuuko Haraguchi、Tomomi Kawano、Hiroto Kaku、Mitsuyo Horikawa、Tetsuto Tsunoda

  DOI：10.1016/j.tetlet.2012.08.095

  日期：2012.10

  A modified version of Markó’s aerobic oxidation procedure, using highly pure (99.995+%) CuCl with 4,7-diphenyl-1,10-phenanthroline (dpPhen), DBAD, and Cs2CO3 (98% purity) successfully oxidized primary and secondary alcohols to the corresponding aldehydes and ketones in excellent yield at room temperature with either air or molecular oxygen under atmospheric pressure.

  马可（Markó）有氧氧化程序的改良版，使用高纯度（99.995 +％）CuCl与4,7-二苯基-1,10-菲咯啉（dpPhen），DBAD和Cs 2 CO 3（纯度98％）成功地氧化了伯室温下，在空气或分子氧的作用下，仲醇与相应的醛和酮的收率极高。
• Oxidation of alkanols into “symmetric” esters with the system Ce(SO4)2—LiBr
  作者：G. I. Nikishin、L. L. Sokova、N. I. Kapustina

  DOI：10.1007/s11172-010-0006-6

  日期：2009.2

  A method for the synthesis of “symmetric” esters based on the oxidation of primary straight-and iso-chain aliphatic alcohols C6 —C11 with the system Ce(SO4)2—LiBr in water has been suggested.

  提出了一种合成“对称”酯的方法，该方法基于在水中使用Ce(SO4)2—LiBr体系对C6—C11的原料直链和异链脂肪醇进行氧化。
• Dehydrogenative Coupling of Primary Alcohols To Form Esters Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex
  作者：Amanda Sølvhøj、Robert Madsen

  DOI：10.1021/om200928b

  日期：2011.11.14

  The ruthenium complex [RuCl2(IiPr)(p-cymene)] catalyzes the direct condensation of primary alcohols into esters and lactones with the release of hydrogen gas. The reaction is most effective with linear aliphatic alcohols and 1,4-diols and is believed to proceed with a ruthenium dihydride as the catalytically active species.