allyl hex-2-ynoate | 143372-03-6

• 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: allyl hex-2-ynoate
• 英文别名: Prop-2-enyl hex-2-ynoate
• CAS: 143372-03-6
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: QXIWWBQIQAOJKH-UHFFFAOYSA-N

物化性质

• 沸点：
  221.7±19.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl hex-2-ynoate 在 三丁基膦 作用下， 以 苯 为溶剂， 反应 48.0h， 以80%的产率得到山梨酸烯丙酯
  参考文献：
  名称：

  Guo, Cheng; Lu, Xiyan, Journal of the Chemical Society. Perkin transactions I, 1993, # 16, p. 1921 - 1924

  摘要：

  DOI：
• 作为产物：
  描述：

  2-己炔酸 、 3-溴丙烯 在 sodium carbonate 作用下， 以 六甲基磷酰三胺 为溶剂， 以92%的产率得到allyl hex-2-ynoate
  参考文献：
  名称：

  Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications

  摘要：

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.

  DOI：

  10.1021/jo00110a018

文献信息

• Chemo-, Regio-, and Stereoselective Copper(II)-Catalyzed Boron Addition to Acetylenic Esters and Amides in Aqueous Media
  作者：Amanda K. Nelson、Cheryl L. Peck、Sean M. Rafferty、Webster L. Santos

  DOI：10.1021/acs.joc.6b00648

  日期：2016.5.20

  Aqueous conditions were developed for conducting an open-to-air, copper(II)-catalyzed addition of pinBBdan to alkynoates and alkynamides. The simple and mild β-borylation protocol proceeds in a remarkably chemo-, regio-, and stereoselective fashion to afford 1,8-diaminonaphthalene protected (Z)-β-boryl enoates and primary, secondary, and tertiary enamides in good to excellent yields. These reactions

  开发了在露天条件下进行铜（II）催化的pinBBdan加至炔酸和炔酰胺中的露天条件。简单而温和的β-硼化协议以显着的化学，区域和立体选择性方式进行，从而以良好的产率提供了1,8-二氨基萘保护的（Z）-β-硼烯酸酯和伯，仲和叔酰胺。 。这些反应显示出对各种烷基，芳基和杂原子官能团的高耐受性，并提供了对各种乙烯基硼酸衍生物的方便获得。
• Extending the Salinilactone Family
  作者：Christian Schlawis、Tim Harig、Stephanie Ehlers、Dulce G. Guillen‐Matus、Kaitlin E. Creamer、Paul R. Jensen、Stefan Schulz

  DOI：10.1002/cbic.201900764

  日期：2020.6.2

  Finding further function : Five new salinilactones have been identified by GC/MS and synthesis, thereby extending the family of salinilactones to eight compounds. Inhibition assays with actinomycetes, tracking of salinilactone production in Salinispora bacteria, and brine shrimp assays provided insight into the occurrence and biological purpose of salinilactones.

  寻找进一步的功能：通过 GC/MS 和合成鉴定了五种新的盐内酯，从而将盐内酯家族扩展到八种化合物。放线菌的抑制测定、盐孢菌中盐内酯产生的追踪以及丰年虾测定提供了对盐内酯的发生和生物学目的的深入了解。
• Efficient Synthesis of α-Allylbutenolides from Allyl Ynoates via Tandem Ligand-Enabled Au(I) Catalysis and the Claisen Rearrangement
  作者：Huiyan Wang、Ting Li、Zhitong Zheng、Liming Zhang

  DOI：10.1021/acscatal.9b03501

  日期：2019.11.1

  A facile construction of α-allylbutenolides from readily available allyl ynoates has been developed via tandem gold-catalyzed alkyne isomerization to allene and cycloisomerization, the Claisen rearrangement and a double bond migration. The gold catalysis is enabled by a bifunctional phosphine ligand featuring a critical remote tertiary amino group, and the reaction tolerates a range of substituents

  通过串联金催化的炔烃异构化为丙二烯和环异构化，克莱森重排和双键迁移，已经开发了一种由易得的烯丙基壬酸酯容易地构建α-烯丙基丁烯化物的方法。金的催化作用是通过具有关键的远端叔氨基的双功能膦配体实现的，该反应可耐受一系列取代基，收率最高可达96％。
• Molecular oxygen promoted oxidative cleavage of carbon-palladium bonds — catalytic cyclization of allylic 2-alkynoates to α-alkylidine-γ-butyrolactones by a PdII complex
  作者：Guoxin Zhu、Xiyan Lu

  DOI：10.1016/0022-328x(95)05781-j

  日期：1996.2

  Molecular oxygen was used as the oxidant to promote the PdII and CuII catalyzed cyclization of acyclic allylic 2-alkynoates, yielding α-haloakylidene-gg-butyrokactones with high stereoselectivity. The stereochemitsyr of halopalladation of the carbon-carbon triple bond, 1,2-induction in the intramolecular carbon-carbon double insertion and oxidative cleavage of carbon-palladium bonds in the cyclization

  分子氧用作氧化剂，以促进Pd II和Cu II催化无环烯丙基2-链烷酸酯的环化反应，产生具有高立体选择性的α-卤代亚烷基-gg-丁酮内酯。详细研究了碳-碳三键的卤代缩合的立体化学，分子内碳-碳双插入的1,2-诱导和环化反应中碳-钯键的氧化裂解。
• OXYGEN SCAVENGERS
  申请人：M&G USA Corporation

  公开号：US20140220281A1

  公开（公告）日：2014-08-07

  Described herein are oxygen scavengers, oxygen scavenging polymeric compositions, and oxygen scavenging articles. The polymeric compositions comprising the oxygen scavengers may have utility in packaging, sealing, wrapping, and storing oxygen-sensitive substances, e.g., to preserve freshness of foods, beverages, and the like.

  本文介绍了氧气清除剂、氧气清除聚合物组合物和氧气清除物品。含氧气清除剂的聚合物组合物可用于包装、封装、包裹和储存对氧气敏感的物质，例如保持食品、饮料等的新鲜度。