2,5-呋喃二酮,二氢-3-(1-十八碳烯-1-基)- | 28777-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,5-呋喃二酮,二氢-3-(1-十八碳烯-1-基)-
• 英文名称: octadec-1-en-1-ylsuccinic anhydride
• 英文别名: octadecenyl succinic anhydride；3-octadec-1-enyloxolane-2,5-dione
• CAS: 28777-98-2；19024-74-9
• 化学式: C₂₂H₃₈O₃
• mdl: MFCD00061084
• 分子量: 350.542
• InChiKey: KAYAKFYASWYOEB-UHFFFAOYSA-N

物化性质

• 沸点：
  466.8±34.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)
• 物理描述：
  Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• RTECS号：
  LU1245000
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  EF24 、 2,5-呋喃二酮,二氢-3-(1-十八碳烯-1-基)- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到3-[3,5-bis-(2-fluorobenzylidene)-4-oxopiperidine-1-carbonyl]octadec-4-enoic acid
  参考文献：
  名称：

  CLEFMA—An anti-proliferative curcuminoid from structure–activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

  摘要：

  3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 <30 mu M), and 16 compounds possessed reduced cell-killing efficacy (IC50 >50 mu M). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzyl-idene-4-oxo-piperidine-1-yl)-4-oxo-2-butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.055
• 作为产物：
  描述：

  十八碳烯 、 马来酸酐 200.0 ℃ 、177.75 kPa 条件下， 反应 4.0h， 以10 torr, leaving the product ODSA (750 grams) in the pot的产率得到2,5-呋喃二酮,二氢-3-(1-十八碳烯-1-基)-
  参考文献：
  名称：

  Comminuted inorganic materials

  摘要：

  根据本发明，提供了一种物质组成物，其包括细碎的无机材料和具有以下公式的取代琥珀酸酐的反应产物：##STR1## 其中R.sub.1、R.sub.2、R.sub.3和R.sub.4中至少有一个是所选取自1到约30个碳原子的烷基、烯基、炔基或芳基烷基或其取代衍生物的取代基，其余取代基为氢。 取代基可以是饱和或不饱和的，线性或支链的，并且可以具有1到约10个取代，包括卤素，三级胺，三级酰胺，缩醛，环硫醚，磺酸盐，膦酸盐，亚酰胺，羧酸盐，碳酸盐，异氰酸酯，硅烷，环氧，氰基，醚，硫醚，羰基，芳香族硝基或缩醛。 在特定分子中，所有的R.sub.1、R.sub.2、R.sub.3和R.sub.4基团可以相同或不同，只要它们属于上述类别。

  公开号：

  US04328041A1

文献信息

• Lactone modified mono-or dicarboxylic acid based adduct dispersant
  申请人：Exxon Chemical Patents Inc.

  公开号：US04906394A1

  公开（公告）日：1990-03-06

  C.sub.5 -C.sub.9 lactone based adduct materials are made by reacting a C.sub.5 -C.sub.9 lactone with a polyamine, a polyol or an amino alcohol to form a lactone adduct intermediate, and thereafter reacting the intermediate with an aliphatic hydrocarbyl saturated or unsaturated, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about one to about 165 total carbon atoms in said straight or branched chain to insure that the resulting lactone adduct is hydrocarbon soluble. The resulting adduct material are useful per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.

  C.sub.5-C.sub.9内酯基加合物材料是通过将C.sub.5-C.sub.9内酯与多胺，多元醇或氨基醇反应，形成内酯加合物中间体，然后将中间体与具有直链或支链的饱和或不饱和，单羧酸或双羧酸基的脂肪族烃基反应，该烃基在直链或支链中具有大约1到165个总碳原子，以确保所得到的内酯加合物是烃溶性的。所得到的加合物材料本身就有用，作为油溶性分散剂添加剂，并且在包含添加剂的燃料和润滑油组合物中也很有用。
• Substituted succinate esters and low-calorie oils containing them
  申请人：Recot, Inc.

  公开号：US05176933A1

  公开（公告）日：1993-01-05

  Fatty alcohol succinic acid esters of the formula: RCH.dbd.CH--CH.sub.2 --CH(COOR')CH.sub.2 (COOR") wherein R is a linear alkyl group of from 5 to 15 carbon atoms, R' and R" can be the same or different and are linear saturated, monounsaturated or diunsaturated alkyl groups of from 12 to 20 carbon atoms. These fatty alcohol esters can be prepared by reacting succinic anhydrides with long chain fatty alcohols, and have a low calorie value. The compounds are suitable for use in cooking oil compositions for the commercial production of reduced-calorie fried snack foods.

  化学式为：RCH.dbd.CH--CH.sub.2 --CH(COOR')CH.sub.2 (COOR")的脂肪醇琥珀酸酯，其中R为含有5至15个碳原子的直链烷基，R'和R"可以相同或不同，是含有12至20个碳原子的直链饱和、单不饱和或双不饱和烷基。这些脂肪醇酯可以通过将琥珀酸酐与长链脂肪醇反应制备而成，并具有低热量价值。这些化合物适用于用于商业生产低热量油炸小吃食品的烹饪油组合物中。
• Substituted lactone acid materials are friction modifiers
  申请人：Exxon Research & Engineering Co.

  公开号：US04264460A1

  公开（公告）日：1981-04-28

  Substituted lactone acid materials are usefully incorporated into an automatic transmission fluid (ATF) in an at least friction modifying amount to provide the ATF with a reduced rate of torque change normally found in ATF formulations when subjected to oxidative conditions. The sulfur-bridged C.sub.6 -C.sub.30 alkyl lactone acids are preferred.

  替代内酯酸材料被有益地加入到自动变速器液(ATF)中，至少起到减少ATF在氧化条件下正常情况下发生的扭矩变化速率的作用。硫桥接的C.sub.6-C.sub.30烷基内酯酸是首选。
• Lactone modified mono- or dicarboxylic acid based adduct dispersant
  申请人：Exxon Chemical Patents Inc.

  公开号：US05032320A1

  公开（公告）日：1991-07-16

  C.sub.5 -C.sub.9 lactone based adduct materials are made by reacting a C.sub.5 -C.sub.9 lactone with a polyol to form a lactone adduct intermediate, and thereafter reacting the intermediate with an aliphatic hydrocarbyl saturated or unsaturated, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about one to about 165 total carbon atoms in said straight or branched chain to insure that the resulting lactone adduct is hydrocarbon soluble. The resulting adduct material are useful per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.

  C.sub.5-C.sub.9内酯基加合物材料是通过将C.sub.5-C.sub.9内酯与多元醇反应形成内酯加合物中间体，然后将中间体与具有从约1个到约165个总碳原子的直链或支链单羧酸或二羧酸酰化剂进行反应，以确保所得到的内酯加合物是烃溶性的。所得到的加合物材料本身就很有用，作为油溶性分散剂添加剂，并且在包含添加剂的燃料和润滑油组合物中也很有用。
• Alkyl-succinhydrazide additives for lubricants
  申请人：UNIROYAL CHEMICAL COMPANY, INC.

  公开号：US20030104953A1

  公开（公告）日：2003-06-05

  Disclosed herein is a composition comprising: (A) a lubricant, and (B) at least one alkyl succinhydrazide compound of the formula: 1 wherein: R 1 is selected from the group consisting of linear or branched alkyl, alkenyl, alkaryl, alkyl ether, alkyl ester, and alkylene ester groups; R 2 is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkyl ether, and alkyl ester groups; and R 3 and R 4 are independently selected from the group consisting of hydrogen, linear or branched alkyl and alkenyl groups, aryl groups, and alkaryl groups.

  本文揭示了一种组合物，包括：（A）润滑剂和（B）至少一种烷基琥珀酰肼化合物，其化学式为：1，其中：R1选自线性或支链烷基、烯基、烷基芳基、烷基醚、烷基酯和烷基酯基团组成的群；R2选自氢、线性或支链烷基、烯基、烷基醚和烷基酯基团组成的群；R3和R4分别独立选自氢、线性或支链烷基和烯基、芳基和烷基芳基团组成的群。