十一碳-10-酸乙酯 | 94030-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十一碳-10-酸乙酯
• 英文名称: 10-undecynoic acid ethyl ester
• 英文别名: ethyl 10-undecynoate；ethyl ester of dodec-11-ynoic acid；undec-10-ynoic acid ethyl ester；Undec-10-insaeure-aethylester；ω-Acetylenyl-pelargonsaeure-aethylester；Decin-(9)-carbonsaeure-(1)-aethylester；ethyl undec-10-ynoate
• CAS: 94030-75-8
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: RIINEWTVKLQWOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  十一碳-10-酸乙酯 在 三乙基硼 、 dichlorogallane 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 以74%的产率得到10-十一烯酸乙酯
  参考文献：
  名称：

  Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums

  摘要：

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.

  DOI：

  10.1021/jo0344790
• 作为产物：
  描述：

  10,11-dibromo-undecanoic acid 在 氢氧化钾 、 苯 作用下， 生成 十一碳-10-酸乙酯
  参考文献：
  名称：

  Jeffery; Vogel, Journal of the Chemical Society, 1948, p. 663

  摘要：

  DOI：

文献信息

• Synthesis and Biological Activities of Acetylenic Fatty Acids and Their Esters
  作者：Munehiro Nakatani、Yuji Fukunaga、Hiroyuki Haraguchi、Makoto Taniguchi、Tsunao Hase

  DOI：10.1246/bcsj.59.3535

  日期：1986.11

  Eight terminal acetylenic fatty acids from 5-hexynoic to 12-tridecynoic acids and their methyl, ethyl, and isopropyl esters were synthesized via o-nitrophenyl selenides. These acids and esters all showed inhibitory effect on lettuce seed germination and seedling growth. The effect was dependent on the number of carbon atoms in acetylenic chain. 8-Nonynoic acid showed potent activity, and its methyl ester was the most effective among the test compounds. In addition, the acids showed antifungal activity which increased as the number of carbon atoms increased.

  通过邻硝基苯硒醚合成了 8 种末端炔脂肪酸:从 5-己炔酸到 12-十三炔酸及其甲基、乙基和异丙基酯。这些酸和酯对莴苣种子萌发和幼苗生长均有抑制作用。其作用效果依赖于炔链碳原子数。8-壬炔酸具有强烈的活性,其甲酯在所测试样品中活性最强。此外,这些酸具有抗菌活性,且随碳原子数的增加而增强。
• Triethylborane-induced stereoselective radical addition of perfluoroalkyl iodides to acetylenes
  作者：Yoshihiro Takeyama、Yoshifumi Ichinose、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)99190-1

  日期：——

  acetylenes bearing a variety of substituents with perfluoroalkyl iodides in the presence of a catalytic amount of triethylborane provides the corresponding perfluoroalkenes in good to excellent yields. The addition of perfluoroalkyl iodides to olefins is also described.

  在催化量的三乙基硼烷的存在下，用全氟烷基碘处理带有各种取代基的末端或内部乙炔，可以以良好或极好的收率得到相应的全氟烯烃。还描述了将全氟烷基碘化物加到烯烃中。
• A SIMPLE SYNTHESIS OF α,β-UNSATURATED ALDEHYDES BY THE REACTION OF VINYLSILANES WITH DICHLOROMETHYL METHYL ETHER PROMOTED BY TITANIUM(IV) CHLORIDE. APPLICATION TO THE SYNTHESIS OF ETHYL 12-OXO-10(<i>E</i>)-DODECENOATE AND NUCIFERAL
  作者：Keiji Yamamoto、Junichi Yoshitake、Nguyen Thi Qui、Jiro Tsuji

  DOI：10.1246/cl.1978.859

  日期：1978.8.5

  readily underwent formylation with replacement of the silyl group when treated with dichloromethyl methyl ether and titanium(IV) chloride. This reaction provides a simple procedure for the selective preparation of (E)-2-alkenals (2) and was conveniently applied to the synthesis of ethyl 12-oxo-10(E)-dodecenoate and nuciferal.

  当用二氯甲基甲基醚和氯化钛 (IV) 处理时，1,2-二取代乙烯基三甲基硅烷 (1) 很容易发生甲酰化，甲硅烷基被取代。该反应为选择性制备 (E)-2-链烯醛 (2) 提供了一个简单的方法，并方便地应用于 12-oxo-10(E)-十二烯酸乙酯和核素的合成。
• Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence
  作者：Birgit Gockel、Norbert Krause

  DOI：10.1002/ejoc.200901010

  日期：2010.1

  The stereoselective gold-catalyzed 6-endo cyclization of various β-hydroxyallenes in the presence of N-iodosuccinimide affords iodinated dihydropyrans in good yield. Subsequent functionalization by palladium-catalyzed cross coupling opens an access to α-hydroxyallenes that are converted in a second gold-catalyzed cyclization into furopyrans which occur in various natural products.

  在 N-碘代琥珀酰亚胺存在下，各种 β-羟基丙二烯的立体选择性金催化 6-内环化以良好的收率提供碘化二氢吡喃。随后通过钯催化的交叉偶联进行的功能化打开了获得 α-羟基丙二烯的途径，这些α-羟基丙二烯在第二次金催化的环化中转化为呋喃吡喃，呋喃吡喃存在于各种天然产物中。
• A Facile Generation of a Cyclopropylzinc Compound from an Alkenylzinc Derivative and Its Reaction with Electrophiles
  作者：Kentaro Yachi、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/(sici)1521-3773(19981002)37:18<2515::aid-anie2515>3.0.co;2-d

  日期：1998.10.2

  The one-pot synthesis of cyclopropyl compounds from 1-alkynes has been achieved by direct cyclopropanation of a 1-alkenylzinc species upon treatment with iodomethylzinc and trapping of the cyclopropylzinc intermediate with allyl bromide in the presence of CuCN⋅2 LiCl (see reaction scheme). This method proceeds under mild conditions and in good yield.

  通过用碘代甲基锌处理后对1-烯基锌物种进行直接环丙烷化，以及在CuCN⋅2LiCl的存在下用烯丙基溴捕获环丙基锌中间体的方法，可以实现1-炔烃一锅法合成环丙基化合物（参见反应方案） 。该方法在温和条件下以高收率进行。