methyl trans-2-octen-7-ynoate | 136893-91-9

• 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 trans-2-octen-7-ynoate
• 英文别名: (E)-methyl oct-2-en-7-ynoate；methyl (E)-oct-2-en-7-ynoate；methy (2E)-2-octen-7-ynoate
• CAS: 136893-91-9
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: KSFJLKQYGPXUIS-BQYQJAHWSA-N

物化性质

• 沸点：
  210.4±33.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  methyl trans-2-octen-7-ynoate 在 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 生成 tert-Butyl-((E)-4-methoxymethoxy-undec-5-en-10-ynyloxy)-dimethyl-silane
  参考文献：
  名称：

  Synthesis of macrocyclic homopropargylic alcohols through intramolecular SE' addition of allenylstannanes and their subsequent conversion to 2,5-furanocycles

  摘要：

  The 2,5-furanocyclododecenes 16, 20, and 24 have been prepared by a new route involving intramolecular S(E)' addition of propargylic stannanes 3, 6, and 9 then exposure of the derived allenones 14, 19, and 23 to AgN-O3-CaCO3 in aqueous acetone at room temperature.

  DOI：

  10.1021/jo00022a008
• 作为产物：
  描述：

  5-己炔-1-醇 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 0.45h， 生成 methyl trans-2-octen-7-ynoate
  参考文献：
  名称：

  钼和铬卡宾配合物与 1,6- 和 1,7- 烯炔的环化反应：系链长度和组成的影响

  摘要：

  已经观察到，1,6-和1,7-烯炔与五羰基（丁基甲氧基卡宾）钼（0）（18）的反应以良好至极好的产率产生乙烯基环丙烷。已经对控制这些环化成功的因素进行了系统调查。铬卡宾配合物也会导致乙烯基环丙烷的形成，但产率明显较低。当不遵循乙烯基环丙烷的途径时，会获得许多其他不同类型的产品。讨论和比较了导致这些不同产品的途径

  DOI：

  10.1021/ja00048a012

文献信息

• Intramolecular Diels–Alder Reactions of Tethered Enoate Substituted Furans Induced by Dialkylaluminum Chloride
  作者：Sibylle Riedel、Cäcilia Maichle-Mössmer、Martin E. Maier

  DOI：10.1021/acs.joc.7b02117

  日期：2017.12.1

  enoate-substituted furans 14 and 19. While attempts at thermal and several Lewis acid induced intramolecular Diels–Alder reactions remained fruitless, dialkylaluminum chloride led to the formation of hexahydroindene and octahydronaphthalene derivatives 20–23. Their formation can be explained by Lewis acid induced opening of the epoxy bridge with transfer of one alkyl group to the intermediate cycloadduct

  通过Sonogashira偶联获得的金（I）催化的烯醇11和17的环异构化，导致束缚的烯酸酯取代的呋喃14和19。而在热和几个路易斯酸尝试诱导分子内狄尔斯-阿尔德反应仍然不结果，二烷基氯化铝导致hexahydroindene和八氢萘衍生物的形成20 - 23。它们的形成可以通过路易斯酸诱导的环氧桥的打开以及一个烷基转移至中间环加合物来解释。
• Cyclization reactions of molybdenum and chromium carbene complexes with enynes
  作者：Daniel F. Harvey、Kevin P. Lund、David A. Neil

  DOI：10.1016/0040-4039(91)80155-y

  日期：1991.10

  Thermolysis of enynes with pentacarbonyl(butylmethoxycarbene)molybdenum (0) 1a produces vinylcyclopropanes in significantly higher yields than the analogous chromium carbene complexes 1b and 3. Additionally, enynes with an allylic ether substituent are shown to cyclize to vinylcyclopropanes in good to excellent yield.

  用五羰基（butylmethoxycarbene）钼烯炔的热解（0）1A产生在比类似铬卡宾络合物显著更高的产量vinylcyclopropanes 1B和3。另外，具有烯丙基醚取代基的烯炔以良好至优异的产率环化成乙烯基环丙烷。
• Tyrosine specific sequential labeling of proteins
  作者：Gergely B. Cserép、András Herner、Otto S. Wolfbeis、Péter Kele

  DOI：10.1016/j.bmcl.2013.09.002

  日期：2013.11

  We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner. (c) 2013 Elsevier Ltd. All rights reserved.
• On the Reaction of a Dioxenylmolybdenum Carbene Complex with Enynes:  Studies of the Intramolecular Diels−Alder Reaction
  作者：Daniel F. Harvey、Ellen M. Grenzer

  DOI：10.1021/jo9513370

  日期：1996.1.1

  Dioxenylmolybdenum carbene complex 1 has been found to readily react with enynes to form tetracyclic products. The tetracyclic products of this reaction appear to be generated via intramolecular [4 + 2] cycloaddition of an initially formed trialkoxycyclopentadiene derivative. Studies which help to define the generality of this reaction are reported, and the involvement of the metal in the cyclization process is discussed.