13-(甲氧基甲氧基)十三碳-1-烯 | 518333-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 13-(甲氧基甲氧基)十三碳-1-烯
• 英文名称: 12-methoxymethoxy-1-bromododecane
• 英文别名: 1-Bromo-13,15-dioxahexadecane；1-bromo-12-(methoxymethoxy)dodecane
• CAS: 518333-08-9
• 化学式: C₁₄H₂₉BrO₂
• 分子量: 309.287
• InChiKey: VWQHYHIFCIFQJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  14
• 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：

  13-(甲氧基甲氧基)十三碳-1-烯 在 吡啶-N-氧化物 、 盐酸 、 重铬酸吡啶 、 正丁基锂 、 diethylzinc 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.5h， 生成 11-cyclopropylundecanoic acid methyl ester
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100
• 作为产物：
  描述：

  二甲醇缩甲醛 、 12-溴-1-十二烷醇 在 对甲苯磺酸 、 lithium bromide 作用下， 反应 16.0h， 以95%的产率得到13-(甲氧基甲氧基)十三碳-1-烯
  参考文献：
  名称：

  Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes

  摘要：

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.

  DOI：

  10.1021/jo0267100

文献信息

• A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species,<i>Lyclene dharma dharma</i>, in the Family of Arctiidae
  作者：Masanobu YAMAMOTO、Tomoya KAMATA、Nguyen Duc DO、Yasushi ADACHI、Masakatsu KINJO、Tetsu ANDO

  DOI：10.1271/bbb.70551

  日期：2007.11.23

  stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones

  lyclene dharma dharma（Arctiidae，Lithosiinae）的雌蛾产生了三种信息素成分（I-III），强烈刺激了雄性触角。使用GC-MS分析和化学衍生化，估算出以下结构：6-甲基-2-十八烷酮（I），14-甲基-2-十八烷酮（II）和6,14-二甲基-2-十八烷酮（III） 。尽管由于难以收集足够量的天然信息素而不能确定手性中心的立体化学，但通过从二醇开始的外消旋混合物的合成证实了I和II的纯结构。这些甲基支链的酮尚未被鉴定为天然产物，表明它们构成了鳞翅目雌性信息素的新化学基团。
• Versatile and chemoselective synthesis of fluorinated methyl ethers from methoxymethyl ethers
  作者：Reiya Ohta、Yuichi Kuboki、Yuki Yoshikawa、Yasuyuki Koutani、Tomohiro Maegawa、Hiromichi Fujioka

  DOI：10.1016/j.jfluchem.2017.07.007

  日期：2017.9

  developed for the synthesis of aliphatic fluorinated methyl ethers (ROCH2RF), specifically monofluoromethyl ethers (ROCH2F) and trifluoromethylthiomethyl ethers (ROCH2SCF3), through pyridinium-type salt intermediates derived from methoxymethyl (MOM) ethers. The addition of a fluorine source (F− or SCF3−) to the pyridinium-type salts afforded the corresponding fluorinated methyl ethers in good yields under

  通过衍生自甲氧基甲基的吡啶鎓盐类中间体，已开发出一种通用的化学选择路线，用于合成脂族氟化甲基醚（ROCH 2 R F），特别是一氟甲基醚（ROCH 2 F）和三氟甲基硫代甲基醚（ROCH 2 SCF 3）。 （MOM）醚。加入氟源的（F -或SCF 3 - ）的吡啶鎓盐型得到良好的收率相应的氟化甲基醚温和的条件下。值得注意的是，单氟甲基醚的合成仅在5分钟内即可完成。
• CYCLOPHOSPHAZENE COMPOUND, LUBRICANT COMPRISING SAME, AND MAGNETIC DISK
  申请人：MORESCO Corporation

  公开号：EP2565198A1

  公开（公告）日：2013-03-06

  A cyclophosphazene compound of the formula (I), and lubricants and magnetic disks using the compound wherein n is 2, 3 or 4, m is an integer of 1 to 12, R is C1-4 fluoroalkyl and Rf is -CF2O(CF2CF2O)x(CF2O)yCF2- or -CF2CF2O(CF2CF2CF2O)zCF2CF2- in which x, y and z are each 0 or a positive real number to give a number average molecular weight of 500 to 4000 to a fluoropolyether of the formula HOCH2-Rf-CH2OH including said Rf, the fluoropolyether having a molecular weight distribution (PD) of 1.0 to 1.5.

  式 (I) 的环磷氮化合物，以及使用该化合物的润滑剂和磁盘 其中 n 是 2、3 或 4，m 是 1 至 12 的整数，R 是 C1-4 氟烷基，Rf 是 -CF2O(CF2CF2O)x(CF2O)yCF2- 或 -CF2CF2O(CF2CF2CF2O)zCF2CF2- 其中 x、y 和 z 各为 0 或正实数，以使包括所述 Rf 的式 HOCH2-Rf-CH2OH 的含氟聚醚的数均分子量为 500 至 4000，该含氟聚醚的分子量分布 (PD) 为 1.0 至 1.5。
• US8936859B2
  申请人：——

  公开号：US8936859B2

  公开（公告）日：2015-01-20
• Enzymatic Desaturation of Fatty Acids:  Δ¹¹ Desaturase Activity on Cyclopropane Acid Probes
  作者：Gemma Villorbina、Lidia Roura、Francisco Camps、Jesús Joglar、Gemma Fabriàs

  DOI：10.1021/jo0267100

  日期：2003.4.1

  The formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid (1) and its disubstituted derivatives cis- and trans-3-5 has been investigated using the Delta(11) desaturase of Spodoptera littoralis as model enzyme. Gas chromatography coupled to mass spectrometry analyses of methanolyzed lipidic extracts from tissues incubated with each probe revealed that all the cyclopropyl fatty acids were transformed into the corresponding 11-cyclopropylidene acids, except for compound trans-5 (5b), which was not desaturated at C11. The formation of methylenecyclopropane 9 as the only reaction product from 1 indicates that a potential radical intermediate is too short-lived to allow rearrangement reactions. Information on the Delta(11) desaturase substrate binding domain is provided considering the cyclopropyl probes 3-5 as conformationally restricted analogues of the straight-chain substrates.