5-heptenal | 73769-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-heptenal
• 英文别名: hept-5-enal
• CAS: 73769-12-7
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: UDOAKURRCZMWOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  -53.35°C (estimate)
• 沸点：
  160.13°C (estimate)
• 密度：
  0.8599 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-heptenal 在 2,6-二甲基吡啶 、 叔丁基锂 、 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-methyl-3-cyclohexene-1-carboxaldehyde dimethyl acetal
  参考文献：
  名称：

  Intramolecular Anodic Olefin Coupling Reactions and the Use of Vinylsilanes

  摘要：

  Intramolecular anodic olefin coupling reactions involving vinylsilane groups have been studied. It was found that the previously successful predictive model for olefin coupling reactions based on an electrophilic attack of a radical cation onto an olefin did not successfully predict product formation for olefin coupling reactions involving vinylsilane terminating groups. Instead, these reactions were best described by viewing the initial addition of the radical cation to an olefin as if it occurred in a reversible ''radical-like'' fashion, in addition, reactions using a temporary silicon tether were shown to be compatible with the formation of quaternary carbons with control of relative stereochemistry. These reactions helped highlight the compatibility of the anodic olefin coupling reactions with extremely sensitive substrates. Finally, the results reported suggest that the mass balance of the intramolecular anodic olefin coupling reaction depends on the ease with which the initially formed cyclized product undergoes the second oxidation step.

  DOI：

  10.1021/ja00087a021
• 作为产物：
  描述：

  5-庚烯-1-醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 5-heptenal
  参考文献：
  名称：

  Intramolecular Anodic Olefin Coupling Reactions and the Use of Vinylsilanes

  摘要：

  Intramolecular anodic olefin coupling reactions involving vinylsilane groups have been studied. It was found that the previously successful predictive model for olefin coupling reactions based on an electrophilic attack of a radical cation onto an olefin did not successfully predict product formation for olefin coupling reactions involving vinylsilane terminating groups. Instead, these reactions were best described by viewing the initial addition of the radical cation to an olefin as if it occurred in a reversible ''radical-like'' fashion, in addition, reactions using a temporary silicon tether were shown to be compatible with the formation of quaternary carbons with control of relative stereochemistry. These reactions helped highlight the compatibility of the anodic olefin coupling reactions with extremely sensitive substrates. Finally, the results reported suggest that the mass balance of the intramolecular anodic olefin coupling reaction depends on the ease with which the initially formed cyclized product undergoes the second oxidation step.

  DOI：

  10.1021/ja00087a021

文献信息

• Organoleptic compound
  申请人：Payne Richard K.

  公开号：US08772533B1

  公开（公告）日：2014-07-08

  The present invention is directed to a novel compound, but-2-enoic acid 1-ethyl-2-methyl-propyl ester, and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of but-2-enoic acid 1-ethyl-2-methyl-propyl ester.

  本发明涉及一种新型化合物，丙烯酸1-乙基-2-甲基-丙基酯，以及通过添加一定量的丙烯酸1-乙基-2-甲基-丙基酯来改善、增强或修改香精配方的方法。
• Photochemistry of 2-(Trifluoromethyl) cyclohexanone
  作者：Christoph Semisch、Paul Margaretha

  DOI：10.1002/hlca.19840670305

  日期：1984.5.2

  The photochemical behaviour of the title compound 1a is compared to that of the non-fluorinated parent ketone 2-methylcyclohexanone (1b). Substitution of the CH3- group on C(2) by a trifluoromethyl group strongly enhances 2H- and RH- reduction product formation in cyclohexane or 2-propanol and oxetane formation in the presence of 2-methylpropene as olefinic component. Under all these conditions 1b

  将标题化合物1a的光化学行为与未氟化的母体酮2-甲基环己酮（1b）的光化学行为进行比较。用三氟甲基取代C（2）上的CH 3-基团可显着增强在环己烷或2-丙醇中2H-和RH-还原产物的形成以及在以2-甲基丙烯为烯烃组分的情况下氧杂环丁烷的形成。在所有这些条件下图1B只经历一-cleavage，一种用于观察1A仅在非还原性溶剂如苯或叔丁基醇。
• Highly regioselective hydroformylation of 1,5-hexadiene to linear dialdehyde catalyzed by rhodium complexes with tetraphosphorus ligands
  作者：Shichao Yu、Yu-ming Chie、Xiaowei Zhang、Liyan Dai、Xumu Zhang

  DOI：10.1016/j.tetlet.2009.07.066

  日期：2009.10

  Rhodium-catalyzed hydroformylation of 1,5-hexadiene to corresponding dialdehydes was investigated using tetraphosphorus ligands. These ligands showed a high regioselectivity for linear aldehydes (linear to branch ratio up to 98%) in very good yield (up to 87%). It was found that the introduction of the substituents at the ortho position of the biphenyl moiety has little effect on the regioselectivity and the

  使用四磷配体研究了铑催化的1,5-己二烯加氢成相应的二醛的加氢甲酰化反应。这些配体对线性醛具有很高的区域选择性（线性支化比高达98％），产率很高（高达87％）。发现在联苯部分的邻位引入取代基对区域选择性几乎没有影响，并且供电子取代基在某种程度上阻碍了反应。
• Stereochemical requirements of acetylenic retro-ene transition states
  作者：Alfred Viola、John J. Collins

  DOI：10.1039/c39800001247

  日期：——

  Retro-ene reactions of acetylenic and olefinic substrates differ in the stereochemical requirements of their respective transition states; reactions of olefins proceed via a chair-like (or boat-like) configuration while those of acetylenes require planarity.

  炔属和烯烃类底物的逆烯反应在其各自过渡态的立体化学要求上有所不同。烯烃的反应通过椅子样（或船形）构型进行，而乙炔的反应则需要平面性。
• Organophotocatalytic N–O Bond Cleavage of Weinreb Amides: Mechanism-Guided Evolution of a PET to ConPET Platform
  作者：Julia Soika、Calum McLaughlin、Tomáš Neveselý、Constantin G. Daniliuc、John. J. Molloy、Ryan Gilmour

  DOI：10.1021/acscatal.2c02991

  日期：2022.8.19

  A mild, organophotocatalytic N–O bond cleavage of Weinreb amides is disclosed, thereby expanding the chemistry of this venerable motif beyond acylation. This redox neutral process begins to reconcile the ubiquity of N–O bonds in contemporary synthesis with the disproportionately harsh, stoichiometric conditions that are often required for bond cleavage. The strategy is compatible with the parent alkyl

  Weinreb 酰胺的温和、有机光催化 N-O 键裂解，从而将这一古老基序的化学扩展到酰化之外。这种氧化还原中性过程开始调和当代合成中普遍存在的 N-O 键与键断裂通常所需的不成比例的苛刻化学计量条件。该策略与母体烷基衍生物（N-OMe、N-OAlkyl）兼容，从而补充了定制的O- 需要 N-OAr 基团的取代基方法（Ar = 缺电子）。公开了广泛的无环和环状衍生物（>40 个实例，高达 95%），并且该方法的合成效用在一系列应用中得到证明。在环状 Weinreb 酰胺衍生物的情况下，该平台能够在一次转化中生成不同链长的两亲酰胺醛。受 Emil Fischer 1908 年使用钠汞齐合成氨基乙醛的开创性启发，这种方法提供了一种更温和的途径来获得这类重要的材料。机械引导的反应发展证明了光诱导电子转移 (PET) 机制的参与，这已进一步发展为连续光诱导电子转移 (ConPET) 歧管：