isopropyl 10,11-epoxyundecanoate | 197149-64-7

• 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: isopropyl 10,11-epoxyundecanoate
• 英文别名: isopropyl 9-(2-oxiranyl)nonanoate；Propan-2-yl 9-(oxiran-2-yl)nonanoate
• CAS: 197149-64-7
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: QQHJZOJYYMNPEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl 10,11-epoxyundecanoate 在 草酰氯 、 Lipase PS 、 potassium carbonate 、 二甲基亚砜 、 二乙胺 、 三乙胺 、 间氯过氧苯甲酸 、 丙腈 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 34.5h， 生成 (+/-)-13-hydroxy-10-oxo-trans-11-octadecenoic acid
  参考文献：
  名称：

  Convenient Formation of 4-Hydroxyalk-2-en-1-one Functionality via A Knoevenagel-type Carbon Chain Elongation Reaction of Aldehyde with 1-Arylsulfinylalkan-2-one

  摘要：

  A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [(RCH)-C-2(OH)CH=CHCOR1], was conveniently prepared by a reaction of an aldehyde ((RCH2CHO)-C-2) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R-1, R-2) did not prevent this reaction. This reaction was used to conveniently prepare (+/-)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.

  DOI：

  10.1021/jo001323g
• 作为产物：
  描述：

  2-十一烯酸 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 isopropyl 10,11-epoxyundecanoate
  参考文献：
  名称：

  不饱和酸和二氧化碳高效合成环状碳酸酯及其在生物基聚氨酯合成中的应用

  摘要：

  生物衍生的呋喃和二酸衍生的环状碳酸酯已经由末端环氧化物和 CO 2以高产率合成。此外，在某些情况下，以良好的收率和出色的非对映选择性分离了四种高度取代的萜烯衍生环状碳酸酯。在温和的反应条件下，由 10-十一碳烯酸衍生制备了 11 种新的环状碳酸酯，以优异的收率提供了相应的碳酸酯产品。该催化剂体系还在相对温和的反应条件（80°C，20 bar，24 小时）下将环氧化脂肪酸正戊酯转化为环状碳酸酯。这种双（环状碳酸酯）以高产率和不同的顺式/反式获得比例取决于所用的助催化剂。当双（三苯基膦）亚胺氯化物用作助催化剂时，仅观察到烯丙醇副产物作为次要产物。最后，使用两种环状碳酸酯作为结构单元，通过与 1,4-二氨基丁烷反应制备非异氰酸酯聚（羟基）氨基甲酸酯。

  DOI：

  10.1002/cplu.202100079

文献信息

• Convenient synthesis of cytotoxic (11E)-13-hydroxy-10-oxooctadec-11-enoic acid from undec-10-enoic acid
  作者：Junzo Nokami、Masahiro Osafune、Kazuhiro Shiraishi、Shin-ichi Sumida、Nobuyuki Imai

  DOI：10.1039/a706245a

  日期：——

  (11E)-13-Hydroxy-10-oxooctadec-11-enoic acid 1 is conveniently synthesized via a Knoevenagel-type reaction of isopropyl 11-phenylsulfinyl-10-oxoundecanoate 2a (itself easily derived from undec-10-enoic acid) with heptanal to form the γ-hydroxyenone functionality together with carbon chain elongation.

  (11E)-13-羟基-10-氧代十八-11-烯酸 1 通过 11-苯基亚磺酰基-10-氧代十一烷酸异丙酯 2a（本身很容易衍生自十一-10-烯酸）与庚醛的 Knoevenagel 型反应方便地合成形成γ-羟基烯酮官能团以及碳链伸长。
• Visible-Light-Promoted Reduction of Epoxides, Hydroxysulfonates, and Halohydrines with Alkyltitanium Alkoxides
  作者：Artyom Mikhaliov、Aliaksei Flerko、Dziyana Atroshchanka、Aliaksei Harakhouski、Arsenii Budko、Kirill Stasko、Andrei Bialkevich、Siarhei Shepialevich、Yahor Rusakovich、Alaksiej Hurski

  DOI：10.1021/acs.orglett.3c03802

  日期：2024.1.12

  Alkyltitanium alkoxides generally serve as nucleophiles in reactions with carbonyl compounds and cross-coupling. Their application as reductants is known but remains underdeveloped. Here, we report that irradiation with visible light makes these organometallic compounds efficient reducing agents for the dehalogenation of 1,2- and 1,3-haloalcohols. This reaction was utilized for the reduction of epoxides

  烷基钛醇盐通常在与羰基化合物的反应和交叉偶联中充当亲核试剂。它们作为还原剂的应用是已知的，但仍未得到开发。在这里，我们报告可见光照射使这些有机金属化合物成为 1,2- 和 1,3- 卤代醇脱卤的有效还原剂。该反应用于环氧化物和磺酸盐的还原，该反应通过一系列原位卤代醇形成和光化学脱卤进行。酯、酰胺、腈、炔和远程溴基团在反应条件下是稳定的。
• Synthesis, Characterization, and Evaluation of 10-Undecenoic Acid-Based Epithio Derivatives as Multifunctional Additives
  作者：Gorla Geethanjali、Korlipara V. Padmaja、Arukali Sammaiah、Rachapudi B. N. Prasad

  DOI：10.1021/jf5033558

  日期：2014.11.26

  Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C-1, C-4, and C-6; isoalkyl, C-3, C-4, and C-8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 8590% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by H-1 and C-13 nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 degrees C) compared to butylated hydroxytoluene (BHT, 193.8 degrees C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.
• Glushko; Petukhova; Klebanskii, Russian Journal of Organic Chemistry, 1997, vol. 33, # 10, p. 1447 - 1451
  作者：Glushko、Petukhova、Klebanskii

  DOI：——

  日期：——
• Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
  作者：Javier Martínez、Felipe Cruz‐Martínez、Marc Martínez de Sarasa Buchaca、Juan Fernández‐Baeza、Luis F. Sánchez‐Barba、Michael North、José A. Castro‐Osma、Agustín Lara‐Sánchez

  DOI：10.1002/cplu.202100079

  日期：2021.3

  Bio‐derived furan‐ and diacid‐derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene‐derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10‐undecenoic acid under mild reaction conditions were prepared, providing the corresponding

  生物衍生的呋喃和二酸衍生的环状碳酸酯已经由末端环氧化物和 CO 2以高产率合成。此外，在某些情况下，以良好的收率和出色的非对映选择性分离了四种高度取代的萜烯衍生环状碳酸酯。在温和的反应条件下，由 10-十一碳烯酸衍生制备了 11 种新的环状碳酸酯，以优异的收率提供了相应的碳酸酯产品。该催化剂体系还在相对温和的反应条件（80°C，20 bar，24 小时）下将环氧化脂肪酸正戊酯转化为环状碳酸酯。这种双（环状碳酸酯）以高产率和不同的顺式/反式获得比例取决于所用的助催化剂。当双（三苯基膦）亚胺氯化物用作助催化剂时，仅观察到烯丙醇副产物作为次要产物。最后，使用两种环状碳酸酯作为结构单元，通过与 1,4-二氨基丁烷反应制备非异氰酸酯聚（羟基）氨基甲酸酯。