(E)-12-hydroxy-2-dodecenoic acid | 13038-05-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E)-12-hydroxy-2-dodecenoic acid
• 英文别名: (E)-12-hydroxydodec-2-enoic acid；12-hydroxydodec-2(E)-enoic acid；12-hydroxy-dodeca-2t-enoic acid；trans-10-Hydroxy-dodecen-(2)-saeure-(1)；12-Hydroxy-trans-dodec-2-en-saeure；trans-12-Hydroxy-dodecan-2-saeure；(2E)-12-hydroxydodec-2-enoic acid
• CAS: 13038-05-6
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: RILFOORPZLBCJK-CSKARUKUSA-N

物化性质

• 熔点：
  70-71 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  365.9±15.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-12-hydroxy-2-dodecenoic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以47%的产率得到2E-dodecen-12-olide
  参考文献：
  名称：

  SEX PHEROMONE DERIVATIVES, AND METHODS AND USES THEREOF

  摘要：

  本公开涉及十二酸酯化十二醇和其制剂，以及其在灰树天牛侵染灰树检测调查和防治方法中的应用。

  公开号：

  US20160205931A1
• 作为产物：
  描述：

  10-十一烯-1-醇 在 双氧水 作用下， 以 甲酸 为溶剂， 生成 (E)-12-hydroxy-2-dodecenoic acid
  参考文献：
  名称：

  Syntheses of 9-Keto- and 10-Hydroxy-trans-2-decenoic Acids and Related Compounds

  摘要：

  DOI：

  10.1021/jo01058a518

文献信息

• Novel Unsaturated Fatty Hydroxy Acid Derivatives and the Dermocosmetologic Use Thereof
  申请人：Charveron Marie

  公开号：US20090238784A1

  公开（公告）日：2009-09-24

  The invention relates to unsaturated fatty hydroxy acid derivatives of formula (I), wherein R n is independent from each other H or linear or branched alkyl group which contain from 1 to 6 carbon atoms and which are possibly substituted by a halogen atom, in particular a fluorine atom, R 1 is H, F, Cl, Br or CF 3 , R is H or linear or branched alkyl group which contain from 1 to 6 carbon atoms and which are possibly substituted by a halogen atom, in particular a fluorine atom and 3=n=14. Said derivatives is suitable for producing an anti-radical, anti-inflammatory and antipruritic dermocosmetologic composition and/or for treating keratinisation and pigmentation troubles and/or for improving healing.

  该发明涉及公式(I)的不饱和脂肪羟基酸衍生物，其中Rn是H或线性或支链烷基基团，含有1至6个碳原子，并且可能被卤素原子（特别是氟原子）取代，R1是H、F、Cl、Br或CF3，R是H或线性或支链烷基基团，含有1至6个碳原子，并且可能被卤素原子（特别是氟原子）取代，3=n=14。所述衍生物适用于生产抗自由基、抗炎和抗瘙痒的皮肤化妆品组合物和/或治疗角化和色素沉着问题和/或改善愈合。
• Synthesis of 3(Z)-dodecen-12-olide—an aggregation pheromone of the flat grain beetleCryptolestes pusillus (Coleoptera:Cucujidae)
  作者：A. A. Vasil'ev、L. Engman、V. M. Merkulova

  DOI：10.1007/bf02495778

  日期：2000.7

  Abstract3(Z)-Dodecen-12-olide, an aggregation pheromone of the flat grain beetle, was obtained using 1,4-cis-hydrogenation of ethyl 12-hydroxydodeca-2,4-dienoate as a key step. The dienoic ester was synthesized from 10-hydroxydec-2-enal, which, in turn, was prepared from its saturated precursorvia acetal α-bromination followed by phenylselenation/oxidative elimination/hydrolysis.

  摘要 3(Z)-Dodecen-12-olide 是扁粒甲虫的聚集信息素，以 12-羟基十二-2,4-二烯酸乙酯的 1,4-顺式氢化为关键步骤获得。二烯酸酯是由 10-羟基癸-2-烯醛合成的，而 10-羟基癸-2-烯醛又是由其饱和前体通过缩醛 α-溴化，然后苯硒化/氧化消除/水解制备的。
• 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。
• Synthesis of trans-10-hydroxydec-2-enoic acid and related compounds
  作者：G.I. Fray、R.H. Jaeger、E.D. Morgan、Robert Robinson、A.D.B. Sloan

  DOI：10.1016/0040-4020(61)80003-3

  日期：1961.1

  Syntheses of the two stereoisomeric 10-hydroxydec-2-enoic acids are described. The trans-isomer is identical with the main fatty acid isolated from royal jelly of honeybees.

  描述了两种立体异构的10-羟基癸-2-烯酸的合成。的反式-异构体是与来自蜜蜂的蜂王浆分离主脂肪酸相同。