(Z)-3-iodooct-2-enoic acid

• 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: (Z)-3-iodooct-2-enoic acid
• 英文别名: E-2-Octenoic acid, 3-iodo-
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: POSYJRUKPPVIDM-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 (Z)-3-iodooct-2-enoic acid 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以75%的产率得到(Z)-5-benzylidene-4-pentylfuran-2(5H)-one
  参考文献：
  名称：

  轻度无钯条件下铜催化制备γ-亚烷基丁烯内酯和异香豆素

  摘要：

  Abstractmagnified imageA general and efficient copper(I)‐catalyzed cross‐coupling and heterocyclization reaction of terminal alkynes and β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5‐ylidenebutenolides and 3‐substituted isocoumarins with excellent regio‐ and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium‐free.

  DOI：

  10.1002/adsc.200800757
• 作为产物：
  描述：

  2-辛炔酸 在 氢碘酸 作用下， 反应 12.0h， 生成 (Z)-3-iodooct-2-enoic acid
  参考文献：
  名称：

  三烯酸的立体选择性合成：视黄酸和类似物的合成

  摘要：

  通过两个连续的 Stille 反应实现共轭三烯酸的立体选择性构建，第一步包括 (E)-1,2-双(三丁基甲锡烷基)乙烯和三丁基甲锡烷基 (Z)- 或 (E)-3-iodoalk- 的偶联2-烯酸。第二步使用了两种不同的途径：(1) 甲锡基二烯酸试剂和乙烯基碘化物的交叉偶联，或 (2) 乙烯基锡烷试剂和通过碘脱苯甲酸化生成的 5-碘戊二烯酸三丁基甲锡酯的交叉偶联的亚锡烷基。通过衍生自 β-或 α-紫罗兰酮和番红醛的 Negishi 二烯的亚锡基金属化合成的乙烯基锡烷提供了获得立体定义的视黄酸的途径。还通过 Sonogashira 偶联制备了一些类视黄醇和 yne 类似物。

  DOI：

  10.1055/s-2006-950201

文献信息

• Palladium-Catalysed Cross-Coupling of Iodovinylic Acids with Organometallic Reagents. Selective Synthesis of 3,3-Disubstituted Prop-2-enoic Acids
  作者：Mohamed Abarbri、Jérôme Thibonnet、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1055/s-2002-20971

  日期：——

  3,3-Disubstituted prop-2-enoic acids were selectively prepared in good yields under mild experimental conditions via palladium-catalysed cross-coupling of 3-substituted 3-iodobut-2-enoic acids with miscellaneous organometallic reagents using dichlorobis(acetonitrile)palladium(II) as catalyst and DMF as solvent.

  使用二氯双（乙腈）钯，通过钯催化的 3-取代 3-碘丁-2-烯酸与各种有机金属试剂的交叉偶联，在温和的实验条件下选择性地制备 3,3-二取代的丙-2-烯酸(II)作为催化剂，DMF作为溶剂。
• 3,3-Difluoro-1-iodocyclopropenes:  A Simple Synthesis and Their Reactions
  作者：Wei Xu、Qing-Yun Chen

  DOI：10.1021/jo020431v

  日期：2002.12.1

  The [1 + 2] cycloaddition reaction of 1-iodoalkynes with difluorocarbene, generated from the decomposition of FSO2CF2COOSiMe3 in diglyme in the presence of 10 mol % NaF at 120 degreesC, gives 3, 3-difluoro-1-iodocyclopropenes in good yields. These new iodides can be trifluoromethylated and functionalized via the Heck reaction. The unusual hydrolytic reactions of the iodides under acidic conditions was also investigated.
• COMPOSITIONS AND RELATED METHODS FOR AGRICULTURE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US20210289794A1

  公开（公告）日：2021-09-23

  The invention comprises methods for decreasing colonization by a bacterium of a gut of a stink bug, the method comprising providing a composition comprising vanillin or an analog thereof; and delivering said composition to an egg from which the stink bug will hatch, whereby colonization by the bacterium within the gut of the stink bug hatched from the egg treated with the composition is decreased relative to a stink bug hatched from an untreated egg. In some embodiments, the decrease in colonization by the bacterium decreases the fitness of the stink bug, e.g., decreases reproductive ability, survival, rate of development, number of eggs, number of hatched eggs, adult emergence rate, body length, body width, body mass, or cuticle thickness. In some embodiments of the methods herein, the bacterial colonization-disrupting agent is an inhibitor of bacterial metabolism. In some embodiments, the bacterial colonization-disrupting agent is a polyhydroxyalkanoate (PHA) synthesis inhibitor.