methyl (E)-pent-2-en-4-ynoate | 41345-43-1

• 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: methyl (E)-pent-2-en-4-ynoate
• CAS: 41345-43-1
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: AHMIYBXPGOFGQT-SNAWJCMRSA-N

物化性质

• 沸点：
  125.2±23.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  methyl (E)-pent-2-en-4-ynoate 在 盐酸 、 ammonium chloride 、 copper(l) chloride 作用下， 生成 deca-2t,8t-diene-4,6-diynedioic acid dimethyl ester
  参考文献：
  名称：

  Bu'Lock et al., Journal of the Chemical Society, 1957, p. 1607,1614

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E)-5-(trimethylsilyl)pent-2-en-4-ynoate 在 四丁基氟化铵 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以74%的产率得到methyl (E)-pent-2-en-4-ynoate
  参考文献：
  名称：

  Synthesis of isomeric polyacetylenes based on natural hydroxy matricaria esters

  摘要：

  The construction of a library of natural and related polyacetylenes using a convergent synthetic strategy based on a palladium mediated cross-coupling reaction is described. The systematic synthetic study led to all possible alkene isomers of the hydroxy matricaria esters 29-32, and the corresponding tiglates 1-4. The synthesis of many of these compounds is described for the first time. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.082

文献信息

• Natural acetylenes. Part XL. Syntheses of polyacetylenic C18 and C16 esters with 9-ene-12,14-diyne unsaturation, and their labelling
  作者：Alexander G. Fallis、Milton T. W. Hearn、Ewart R. H. Jones、Viktor Thaller、John L. Turner

  DOI：10.1039/p19730000743

  日期：——

  The esters R[CC]2·CH2CH[graphics omitted]CH·[CH2]7·CO2MeR = Me[CH2]2, MeCC, cis- or trans-MeCHCH, trans-HO·CH2·CHCH, HO·CH2·CC, cis- or trans-MeO2C·CHCH, MeO2C·CC, (EtO)2CH, OHC, or, H2N·OC} were prepared from the Wittig salt Me3Si·CC·CH2·CH2·PPh3I–via ICC·CH2·CH[graphics omitted]CH·[CH2]7·CO2Me; several were specifically labelled [at C(9), C(17), and C(18)]. The Wittig salt offers a general route

  酯R [C C] 2 ·CH 2 CH [省略图形] CH·[CH 2 ] 7 ·CO 2 Me R = Me [CH 2 ] 2，MeC C，顺式或反式-MeCH CH，反式- HO·CH 2 ·CH CH，HO·CH 2 ·C C，顺式-或反式-MeO 2 C·CH CH，的MeO 2 C·ç C，（ETO）2 CH，OHC，或者，H 2 N·OC }由维蒂希盐Me 3 Si·C C·CH制备2 ·CH 2 ·PPh 3 I –通过ICC·CH 2 ·CH [省略图形] CH·[CH 2 ] 7 ·CO 2 Me；其中几个被专门标记[在C（9），C（17）和C（18）]。维蒂希盐为通向1-烯-4,6-二炔和更高度不饱和的跳过的烯炔体系提供了一条一般路线。
• Rhodium‐Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes
  作者：Hua Chen、Yi Chen、Xiaoxiao Tang、Shunfa Liu、Runping Wang、Tianbao Hu、Lu Gao、Zhenlei Song

  DOI：10.1002/anie.201814143

  日期：2019.3.26

  A Rh‐catalyzed reaction of silacyclobutanes (SCBs) with unactivated alkynes has been developed to form silacyclohexenes with high chemoselectivity. Good enantioselectivity at the stereogenic silicon center was achieved using a chiral phosphoramidite ligand. The resulting silacyclohexenes are useful scaffolds for synthesizing structurally attractive silacyclic compounds.

  硅烷环丁烷（SCB）与未活化炔烃的Rh催化反应已被开发出来，可形成具有高化学选择性的硅烷环己烯。使用手性亚磷酰胺配体在立体硅中心具有良好的对映选择性。所得的硅杂环己烯是用于合成结构上有吸引力的硅环化合物的有用的支架。
• In situ alcohol oxidation-Wittig reactions
  作者：Xudong Wei、Richard J.K Taylor

  DOI：10.1016/s0040-4039(98)00592-9

  日期：1998.5

  alcohols can be oxidised with activated manganese dioxide in the presence of stabilised Wittig reagents to generate α,β-unsaturated esters directly. This simple procedure, which can also be utilised with diols to give double homologation, is generally useful and particularly valuable if the intermediate aldehydes are difficult to isolate, toxic or prone to isomerisation.

  烯丙醇，炔丙醇和苄醇可以在稳定的Wittig试剂存在下用活化的二氧化锰氧化，以直接生成α，β-不饱和酯。如果中间体醛难以分离，有毒或易于异构化，这种简单的方法（也可以与二醇一起使用以提供双重同系物）通常是有用的，并且特别有价值。
• Development of a new epidermal growth factor receptor positron emission tomography imaging agent based on the 3-cyanoquinoline core: Synthesis and biological evaluation
  作者：Federica Pisaneschi、Quang-De Nguyen、Elham Shamsaei、Matthias Glaser、Edward Robins、Maciej Kaliszczak、Graham Smith、Alan C. Spivey、Eric O. Aboagye

  DOI：10.1016/j.bmc.2010.08.004

  日期：2010.9

  97 ± 9.06 nM), low lipophilicity and good metabolic stability. ‘Click’ labeling afforded [18F]16 in 37.0 ± 3.6% decay corrected radiochemical yield based on azide [18F]14 and 7% end of synthesis (EOS) yield from aqueous fluoride. Compound [18F]16 was obtained with >99% radiochemical purity in a total synthesis time of 3 h. The compound showed good stability in vivo and a fourfold higher uptake in high

  表皮生长因子受体 (EGFR/c-ErbB1/HER1) 在许多癌症中过度表达，包括乳腺癌、卵巢癌、子宫内膜癌和非小细胞肺癌。EGFR 特异性显像剂可以促进原发肿瘤和/或转移瘤的临床评估。为了实现这一目标，我们设计并合成了一系列基于 3-氰基喹啉核心的含氟化合物。铅化合物，16，结合-2'-氟乙基-1,2,3-三唑被选择用于评价作为基于其对EGFR高亲和力放射性配体激酶（IC 50  = 1.81±0.18 nM）的，良好的细胞效力（IC 50  = 21.97 ± 9.06 nM)，低亲脂性和良好的代谢稳定性。提供“点击”标签 [ 18 F] 16在基于叠氮化物 [ 18 F] 14 的37.0 ± 3.6% 衰减校正放射化学收率和来自氟化物水溶液的 7% 合成结束 (EOS) 收率。在3小时的总合成时间内以>99%的放射化学纯度获得化合物[ 18 F] 16。与低表达 EGFR 的 HCT116
• QUINOLINE DERIVATIVES USED AS PET IMAGING AGENTS
  申请人：Pisaneschi Federica

  公开号：US20130116206A1

  公开（公告）日：2013-05-09

  There is provided compounds of formula (I), wherein R 1 , R 2 , X 1 , X 2 , and X 3 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as positron emission tomography (PET) imaging agents, useful in the treatment of diseases in which inhibition of epidermal growth factor receptor tyrosine kinase activity or the inhibition of HER2 activity is desired and/or required, and useful in the treatment of cancer.

  提供了化合物的公式(I)，其中R1、R2、X1、X2和X3的含义如描述中所示，并且其药学上可接受的盐，这些化合物可用作正电子发射断层扫描（PET）成像剂，对于需要或要求抑制表皮生长因子受体酪氨酸激酶活性或抑制HER2活性的疾病的治疗非常有用，也用于癌症的治疗。

表征谱图