(E)-8-oxo-non-2-enoic acid | 40980-02-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (E)-8-oxo-non-2-enoic acid
• 英文别名: (E)-8-oxonon-2-enoic acid；trans-8-Oxo-nonen-(2)-saeure-(1)
• CAS: 40980-02-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: DLLIKHDFYLCDGC-FNORWQNLSA-N

物化性质

• 熔点：
  46-51 °C
• 沸点：
  135-140 °C(Press: 1 Torr)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-8-oxo-non-2-enoic acid 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 trans-(Acetyl-2-cyclopentyl)-essigsaeuremethylester
  参考文献：
  名称：

  Moreau,C. et al., Bulletin de la Societe Chimique de France, 1970, p. 545 - 549

  摘要：

  DOI：
• 作为产物：
  描述：

  6-oxoheptanal 、 丙二酸 以 吡啶 为溶剂， 生成 (E)-8-oxo-non-2-enoic acid
  参考文献：
  名称：

  Barbier,M.; Huegel,M.-F., Bulletin de la Societe Chimique de France, 1961, p. 951 - 954

  摘要：

  DOI：

文献信息

• METHOD FOR THE DECARBOXYLATIVE HYDROFORMYLATION OF ALPHA, BETA- UNSATURATED CARBOXYLIC ACIDS
  申请人：Rudolph Jens

  公开号：US20110028746A1

  公开（公告）日：2011-02-03

  The present invention relates to a process for preparing aldehydes by reacting an α,β-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R 1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(═O)OH group of the compound of the formula (I); R 2 , R 3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y 2 and Y 3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y 1,2,3 are each, independently of one another, O, S, NR a or SiR b R c , where R a,b,c are each H or in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; and the use of the above-described catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids.

  本发明涉及一种通过在过渡元素周期表第VIII族金属的至少一个配合物存在下，将α，β-不饱和羧酸或其盐与一氧化碳和氢反应制备醛的方法，所述配合物的化学式为(I)，其中Pn为氮族元素；W为具有1到8个桥连原子的二价桥联基团；R1为能够与化合物的化学式(I)中的—X(═O)OH基团形成至少一种分子间非共价键的官能团；R2、R3在每种情况下均为可选择的取代烷基、环烷基、杂环烷基、芳基或杂芳基，或者与氮族原子以及Y2和Y3基团（如存在）一起形成一个可选择的融合和可选择的取代的5到8元杂环；a、b和c分别为0或1；Y1、2、3各自独立地为O、S、NRa或SiRbRc，其中Ra、b、c各自为H或可选择的取代烷基、环烷基、杂环烷基、芳基或杂芳基；以及上述催化剂用于α，β-不饱和羧酸的脱羧氢甲酰化。
• Tandem decarboxylative hydroformylation–hydrogenation reaction of α,β-unsaturated carboxylic acids toward aliphatic alcohols under mild conditions employing a supramolecular catalyst system
  作者：Lisa Diab、Urs Gellrich、Bernhard Breit

  DOI：10.1039/c3cc45547e

  日期：——

  under mild reaction conditions, compatible with a wide range reactive functional groups, is reported. The new methodology consists of a novel tandem decarboxylative hydroformylation/aldehyde reduction sequence employing a unique supramolecular catalyst system.

  报道了一种新的原子经济催化方法，该方法可在温和的反应条件下将α，β-不饱和羧酸高度化学选择性还原为相应的饱和醇，并与广泛的反应性官能团相容。新方法包括采用独特的超分子催化剂体系的新型串联脱羧加氢甲酰化/醛还原序列。
• Practical Synthesis of (E)-α,β-Unsaturated Carboxylic Acids Using a One-Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence
  作者：Susanne T. Kemme、Tomáš Šmejkal、Bernhard Breit

  DOI：10.1002/adsc.200700595

  日期：2008.5.5

  AbstractCombining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner–Knoevenagel reaction allowed for the development of an efficient, one‐pot procedure for the synthesis of (E)‐α,β‐unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)‐α,β‐unsaturated carboxylic acids in good yields and with excellent regio‐ and stereocontrol. The practicability of this process has been demonstrated by a short protecting group‐free synthesis of the queen honeybee pheromones 9‐ODA [(E)‐9‐oxodec‐2‐enoic acid] and 9‐HDA [(E)‐9‐hydroxydec‐2‐enoic acid].
• A Supramolecular Catalyst for the Decarboxylative Hydroformylation of α,β-Unsaturated Carboxylic Acids
  作者：Tomáš Šmejkal、Bernhard Breit

  DOI：10.1002/anie.200800956

  日期：2008.5.13
• Moreau,C. et al., Bulletin de la Societe Chimique de France, 1970, p. 545 - 549
  作者：Moreau,C. et al.

  DOI：——

  日期：——