methyl 9,9-dimethoxynonanoate | 1599-48-0

• 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: methyl 9,9-dimethoxynonanoate
• 英文别名: 9,9-dimethoxynonanoic acid methyl ester；9,9-Dimethoxy-nonansaeure-methylester；Nonanoic acid, 9,9-dimethoxy-, methyl ester
• CAS: 1599-48-0
• 化学式: C₁₂H₂₄O₄
• 分子量: 232.32
• InChiKey: HZWOYQBUELNXHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 9,9-dimethoxynonanoate 在 二异丁基氢化铝 作用下， 以 various solvent(s) 为溶剂， 反应 2.5h， 以90.8%的产率得到9,9-dimethoxynonan-1-ol
  参考文献：
  名称：

  摘要：

  A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L), is developed using ozonolysis-reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.

  DOI：

  10.1023/a:1019683830012
• 作为产物：
  描述：

  油酸甲酯 在 盐酸 、 臭氧 、 溶剂黄146 作用下， 生成 methyl 9,9-dimethoxynonanoate
  参考文献：
  名称：

  Helferich; Schaefer, Chemische Berichte, 1924, vol. 57, p. 1914

  摘要：

  DOI：

文献信息

• Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
  作者：Jae Won Yoo、Youngran Seo、Jong Beom Park、Young Gyu Kim

  DOI：10.1016/j.tet.2019.130883

  日期：2020.2

  Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon

  脂肪醛可通过相同的中间体β，γ-不饱和α-硝基砜，经脯氨酸催化的连续反应制备的相同中间体，通过2–4个反应，与一碳短和一碳长的同源羰基化合物同源。几种脂肪醛与苯磺酰基硝基甲烷。当关键中间体的氧化裂解得到一碳较少的同源羰基化合物时，相同关键中间体的还原随后被氧化产生了更多一碳的同源羰基化合物。
• Direct Synthesis of an α,ω-Diester from 2,7-Octadienol as Bulk Feedstock in Three Tandem Catalytic Steps
  作者：Karoline A. Ostrowski、Dennis Vogelsang、Thomas Seidensticker、Andreas J. Vorholt

  DOI：10.1002/chem.201503785

  日期：2016.1.26

  A new tandem catalytic process was designed and developed as a tool for the direct conversion of the widely available feedstock 2,7‐octadienol into an α,ω‐diester. This innovative auto‐tandem catalysis is atom efficient and consists of three consecutive palladium‐catalysed reactions: ether formation, ether carbonylation and alkoxycarbonylation. By using the design of experiments (DoE) approach, significant

  设计并开发了一种新的串联催化工艺，将其作为将广泛使用的原料2,7-辛二烯醇直接转化为α，ω-二酯的工具。这种创新的自动串联催化是原子有效的，由三个连续的钯催化反应组成：醚形成，醚羰基化和烷氧羰基化。通过使用实验设计（DoE）方法，确定了重要的参数，并优化了所需的α，ω-二酯的收率。模型底物使人们可以更深入地了解反应的进程，因此，发现了反应顺序。此外，通过简单地应用其他配体，可以遵循不同的反应路径，从而可以探索其他新的串联催化序列，并能够获得新的化合物。
• Bifunctional compounds from reaction of alkoxy hydroperoxides with metal salts
  作者：G. Cardinale、J.A.M. Laan、D. Van Der Steen、J.P. Ward

  DOI：10.1016/s0040-4020(01)91447-4

  日期：1985.1

  with ferrous sulfate. C-C bond scission and radical formation was followed by dimerization of the radicals formed. Ozonides reacted similarly. Acyclic and cyclic olefins, including a cyclic enol ether, gave rise to a range of α,ω-disubstituted products in modest yields. By using ferric chloride, ω-chloro esters were obtained from the alkoxy hydroperoxides derived from olefinic esters.

  通过在醇溶液中使烯烃臭氧化而获得的氢过氧化烷氧基用硫酸亚铁处理。CC键断裂和自由基形成之后，是所形成的自由基的二聚化。臭氧反应类似。无环和环状烯烃，包括环状烯醇醚，以适度的收率产生了一系列α，ω-二取代的产物。通过使用氯化铁，从衍生自烯烃酯的烷氧基氢过氧化物获得ω-氯酸酯。
• Ozonolysis of Olefins, II¹; Linseed Oil as a Renewable Resource for Alkyl 3,3-Dialkoxypropanoates
  作者：Martin Mittelbach、Norbert Poklukar

  DOI：10.1055/s-1990-26868

  日期：——

  A new approach to the synthesis of alkyl 3,3-dialkoxypropanoates, which are important intermediates in organic synthesis, starting from fatty acid esters is described. Thus, ozonolysis of methyl linoleate and methyl linolenate in alcoholic hydrogen chloride affords a reaction mixture, from out of which the alkyl 3,3-dialkoxypropanoates can be isolated by fractional distillation in 60-65% yield. Even linseed oil, which contains high amounts of linolic and linolenic acid, can be used as starting material, after conversion into the methyl esters by methanolysis. Byproducts of the ozonolysis can be oxidized to the corresponding carboxylic acids which are valuable intermediates in oleochemistry.

  一种新方法，从脂肪酸酯开始合成有机合成中重要的中间体——烷基3,3-二烷氧基丙酸酯，被描述出来。因此，在含酒精的盐酸中，通过臭氧分解亚麻油酸甲酯和亚麻酸甲酯会产生一种反应混合物，从中可以通过分馏蒸馏以60-65%的产率分离出烷基3,3-二烷氧基丙酸酯。即使是含有大量亚麻油酸和亚麻酸的亚麻籽油，也可以通过甲醇解转化为甲酯后作为起始材料。臭氧分解的副产物可以氧化为相应的羧酸，这些羧酸在油脂化学中是宝贵的中间体。
• Novel Bioactive Phospholipids:  Practical Total Syntheses of Products from the Oxidation of Arachidonic and Linoleic Esters of 2-Lysophosphatidylcholine¹
  作者：Mingjiang Sun、Yijun Deng、Eugenia Batyreva、Wei Sha、Robert G. Salomon

  DOI：10.1021/jo0105383

  日期：2002.5.1

  Total syntheses of nine novel phospholipids were accomplished to facilitate the identification and biological testing of compounds that are generated upon oxidative cleavage of arachidonate and linoleate esters of 2-lysophosphatidylcholine, the two most abundant polyunsaturated phospholipids in low-density lipoprotein. An efficient general synthesis exploiting 2-lithiofuran as a 4-oxo-2-butenoyl carbanion

  完成了九种新型磷脂的总合成，以简化对低密度脂蛋白中两种最丰富的多不饱和磷脂的2-溶血磷脂酰胆碱的花生四烯酸酯和亚油酸酯的氧化裂解后生成的化合物的鉴定和生物学测试。利用2-硫代呋喃作为4-氧代-2-丁烯酰基碳负离子等效物的有效通用合成提供了含有γ-酮-α，β-不饱和羰基官能团的磷脂。通过利用容易的顺式-反式异构化，可以将两种市售的顺式烯烃（2Z）-2-丁烯-1,4-二醇和2,5-二氢呋喃用作制备霍纳-沃兹沃思-埃蒙斯试剂4的原料。 -（二乙氧基磷酰基）-2E-丁烯醛，是合成2,4-二烯醛的重要组成部分。