3-甲基-2-己酸乙酯 | 15677-00-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-甲基-2-己酸乙酯
• 英文名称: ethyl 3-methylhex-2-enoate
• 英文别名: 3-Methyl-hex-2-ensaeure-aethylester；Ethyl 3-methyl-2-hexenoat；3-Propyl-crotonsaeure-ethylester；3-methyl-hex-2-enoic acid ethyl ester
• CAS: 15677-00-6
• 化学式: C₉H₁₆O₂
• mdl: MFCD01941255
• 分子量: 156.225
• InChiKey: HDCPOYMRKNZICF-UHFFFAOYSA-N

物化性质

• 沸点：
  56-63 °C(Press: 1-2 Torr)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  3-甲基-2-己酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以81%的产率得到3-methylhex-2-en-1-ol
  参考文献：
  名称：

  Synthesis and biological activity of permethrinic acid analogs containing various substituents in position 2 of the cyclopropane ring

  摘要：

  A number of permethrinic acid ethyl ester derivatives having various substituents [Et, Pr, Ph, Ph(CH2)n (n = 1, 2), etc.] in position 2 of the cyclopropane ring were synthesized, and their insecticidal acivity against typhoid flies., rice weevils, and bean aphides, as well as juvenoid activity on flour beetle chrysalises, was studied. The newly synthesized Compounds turned out to exhibit weak insecticidal activity against standard insects but pronounced juvenile hormone activity, which differentiates them from permethrinic acid esters.

  DOI：

  10.1134/s107042800808006x
• 作为产物：
  描述：

  3-羟基-3-甲基己酸乙酯 在 phosphorus pentoxide 作用下， 84.0~90.0 ℃ 、3.47 kPa 条件下， 生成 3-甲基-2-己酸乙酯
  参考文献：
  名称：

  Zamojski,A., Roczniki Chemii, 1966, vol. 40, p. 451 - 462

  摘要：

  DOI：

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
  作者：Bram B. C. Peters、Jira Jongcharoenkamol、Suppachai Krajangsri、Pher G. Andersson

  DOI：10.1021/acs.orglett.0c04012

  日期：2021.1.1

  Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir–N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated

  共轭烯酮的不对称氢化是制备光学活性酮的最有效，最直接的方法之一。在这项研究中，手性双齿Ir-N，P络合物被用于进入这些支架，以获得在α和β位置均具有立体中心的酮。获得了高达99％的出色的对映体过量，并具有良好或较高的分离产率。具有挑战性的二烷基取代的底物（很难通过令人满意的手性诱导进行氢化）以高度对映选择性的方式氢化。
• α-Bromo-β,γ-unsaturated ketenes for the synthesis of α-benzylamino-β,γ-unsaturated acids
  作者：Giuliana Cardillo、Serena Fabbroni、Luca Gentilucci、Rossana Perciaccante、Alessandra Tolomelli

  DOI：10.1016/j.tetasy.2003.12.029

  日期：2004.2

  The synthesis of α-benzylamino-β,γ-unsaturated acids has been developed starting from α-bromo-α,β-unsaturated chlorides. Via treatment of the acyl chlorides with (R)-pantolactone in the presence of TEA, the in situ formation of the deconjugated ketenes and their direct transformation into chiral esters was performed. The substitution of bromine with benzylamine, followed by acid hydrolysis, allowed

  从α-溴-α，β-不饱和氯化物开始发展了α-苄氨基-β，γ-不饱和酸的合成。通过在TEA存在下用（R）-泛内酯处理酰氯，原位形成解偶联的烯酮并将其直接转化为手性酯。用苄胺取代溴，然后进行酸水解，可以得到对映异构体富集的α-苄氨基-β，γ-不饱和酸。
• The application of high pressure to some difficult Wittig reactions
  作者：Neil S. Isaacs、Ghazi Najim El-Din

  DOI：10.1016/s0040-4039(00)96078-7

  日期：1987.1

  Wittig reactions, previously shown to be favourably accelerated under pressure have been carried out between the stabilised ylides carboethoxymethylenetriphenylphosphorane and carboethoxy- ethylidinetriphenylphosphorane with a variety of ketones at 9–10 kbar pressure. Successful formation of tri- and tetra-substituted ethylenes is reported.

  在稳定的烷基化物碳乙氧基亚甲基三苯基磷烷和碳乙氧基亚乙基三苯基磷烷之间，在9–10 kbar的压力下，已进行了Wittig反应，该反应先前被证明在压力下会加速。据报道成功地形成了三和四取代的乙烯。
• New Methods for Synthesis of α,β-Unsaturated Carboxylic Esters from Carbonyl Compounds Using Monoanions of Dithiocarbonates, and Dianions of Ethyl Mercaptoacetate and Ethyl 2-Mercaptopropionate
  作者：Kazuhiko Tanaka、Nobuyuki Yamagishi、Rikuhei Tanikaga、Aritsune Kaji

  DOI：10.1246/bcsj.52.3619

  日期：1979.12

  The lithium enolates of O-alkyl S-alkoxycarbonylmethyl dithiocarbonates and monothiocarbonates were found to be efficient reagents for the synthesis of α,β-unsaturated esters from carbonyl compound...

  发现 O-烷基 S-烷氧基羰基甲基二硫代碳酸酯和单硫代碳酸酯的锂烯醇化物是从羰基化合物合成 α,β-不饱和酯的有效试剂...
• Use of unsaturated esters as perfuming ingredients
  申请人：——

  公开号：US20020055455A1

  公开（公告）日：2002-05-09

  The compound of formula 1 in which the wavy line represents a bond having a configuration of the type (Z) or (E), or a mixture of the two configurations; R 1 represents a hydrogen atom, a C 1 to C 4 linear or branched alkyl radical, a methoxy or ethoxycarbonyl radical, or an aryl radical, and R 2 represents a methyl or ethyl group, possess interesting organoleptic properties and can be advantageously used for the preparation of perfuming compositions to which it gives, in particular, a very natural connotation of the pear type.

  公式1的化合物中，波浪线代表具有(Z)或(E)类型或两种配置的混合物的键；R1代表氢原子、C1至C4的线性或支链烷基、甲氧基或乙氧基羰基基团或芳基基团，而R2代表甲基或乙基基团。这些化合物具有有趣的感官特性，并可以优势地用于制备香料组合物，尤其是赋予了非常自然的梨子气味。