5-己酸乙酯 | 54653-25-7

• 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: 5-己酸乙酯
• 英文名称: ethyl hex-5-enoate
• 英文别名: ethyl 5-hexenoate；ethyl ester of 5-hexenoic acid
• CAS: 54653-25-7
• 化学式: C₈H₁₄O₂
• mdl: MFCD00671844
• 分子量: 142.198
• InChiKey: RJLJOXJZWMGEFD-UHFFFAOYSA-N

物化性质

• LogP：
  2.45
• 物理描述：
  Colourless liquid; fruity aroma
• 溶解度：
  insoluble in water; soluble in most non-polar solvents
• 密度：
  0.902-0.912
• 折光率：
  1.430-1.439
• 保留指数：
  965

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.625
• 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：

  5-己酸乙酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以93%的产率得到Ethyl 5,6-epoxyhexanoate
  参考文献：
  名称：

  The conversion of racemic terminal epoxides into either (+)- or (−)-diol γ- and δ-lactones

  摘要：

  描述了将外消旋末端环氧化物转化为(+)-或(−)-diol γ-和δ-内酯的方法，其中水解动力学拆分（HKR）是关键步骤。

  DOI：

  10.1039/b003793l
• 作为产物：
  描述：

  四氢吡喃-2-甲醇 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 sodium 、 铬酸 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 48.08h， 生成 5-己酸乙酯
  参考文献：
  名称：

  Single electron transfer mechanism in the reaction of 1,3-dithianyllithium and alkyl iodides

  摘要：

  The reaction between 2-lithio-1,3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration. This result suggests that the S(N)2 (rather than single electron transfer (SET) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides. When the neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene was used as the substrate halide, 6-11% cyclized alkylated product was obtained. This result suggests that when the S(N)2 pathway is blocked, SET mechanisms become operative to some extent, at least with iodide as the halogen. The reaction of dithianyllithium and (R)-2-iodooctane and 5,5-dimethyl-6-iodo-1-hexene, with hexane as the solvent, proceeds under heterogeneous conditions to bring about complete racemization or cyclization of the respective iodide. These results demonstrate for the first time that 2-lithio-1,3-dithiane can act as electron donor in reactions initiated by electron transfer to alkyl iodides.

  DOI：

  10.1021/jo00004a051

文献信息

• MnO₂ as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
  作者：Rodney A. Fernandes、Gujjula V. Ramakrishna、Venkati Bethi

  DOI：10.1039/d0ob01344g

  日期：——

  PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is

  通过使用 Pd( II ) 催化剂和 MnO 2作为助氧化剂，已经开发了用于将较少探索的高烯丙醇的末端烯烃氧化成 β-羟基甲基酮的高效温和的反应条件。该方法反应条件温和，官能团相容性好，区域选择性和化学选择性高。而我们早期的 PdCl 2 /CrO 3系统/HCl由高烯丙醇产生α，β-不饱和酮，本方法正交提供β-羟基-甲基酮。没有观察到苄基和/或β-羟基的过度氧化或消除。该方法也可以扩展到简单末端烯烃的氧化，以及甲基酮的氧化，显示出其多功能性。展示了姜酚在区域选择性合成中的应用。
• Sunlight Oxidation of Alkyl Aryl Tellurides to the Corresponding Carbonyl Compounds: A New Carbonyl Precursor
  作者：Akihiko Ouchi、Takeshi Hyugano、Chuanxiang Liu

  DOI：10.1021/ol901943f

  日期：2009.11.5

  Alkyl aryl tellurides were efficiently transformed to the corresponding carbonyl compounds by photo-oxidation with sunlight without affecting various functional groups in the alkyl moiety. The tellurides can be used as a new carbonyl precursor, and the photolysis can be conducted without special equipment for light sources.

  通过在不影响烷基部分中各种官能团的情况下用阳光进行光氧化，将烷基芳基碲化物有效地转化为相应的羰基化合物。碲化物可以用作新的羰基前体，并且无需使用专门的光源设备即可进行光解。
• Synthesis of Migrastatin Analogues as Inhibitors of Tumour Cell Migration: Exploring Structural Change in and on the Macrocyclic Ring
  作者：Daniele Lo Re、Ying Zhou、Joanna Mucha、Leigh F. Jones、Lorraine Leahy、Corrado Santocanale、Magdalena Krol、Paul V. Murphy

  DOI：10.1002/chem.201502861

  日期：2015.12.7

  Migrastatin and isomigrastatin analogues have been synthesised in order to contribute to structure–activity studies on tumour cell migration inhibitors. These include macrocycles varying in ring size, functionality and alkene stereochemistry, as well as glucuronides. The synthesis work included application of the Saegusa–Ito reaction for regio‐ and stereoselective unsaturated macroketone formation

  合成了米格他汀和异米格他汀类似物，以促进对肿瘤细胞迁移抑制剂的结构活性研究。这些包括环大小，官能度和烯烃立体化学不同的大环化合物，以及葡糖醛酸苷。合成工作包括应用Saegusa-Ito反应进行区域和立体选择性不饱和大酮形成，非对映选择性布朗烯丙基化以生成9-甲基米格列他汀类似物以及螯合诱导的异化作用以改变葡糖醛酸的构型。化合物在体外针对乳腺癌和胰腺癌细胞系进行了测试，并且在伤口愈合（刮擦）和博登室试验中均观察到了对肿瘤细胞迁移的抑制作用。一种不饱和大酮化合物对一系列次级药物靶标的亲和力低，
• Synthesis of guaipyridine alkaloids (±)-cananodine and (±)-rupestines D and G using an intramolecular Mizoroki-Heck reaction
  作者：Patrick M.M. Shelton、Samantha M. Grosslight、Briana J. Mulligan、Hope V. Spargo、Silvana S. Saad、James R. Vyvyan

  DOI：10.1016/j.tet.2020.131500

  日期：2020.10

  rupestine G were synthesized in six steps or less from readily available 3-(allyloxy)-2-(bromomethyl)-6-methylpyridine. Key steps in the synthesis include an enolate alkylation of the aforementioned substituted picolyl bromide and an intramolecular Mizoroki-Heck reaction to form the seven-membered carbocycle of the target compounds.

  从易得的3-（烯丙氧基）-2-（溴甲基）-6-甲基吡啶以六个步骤或更少的步骤合成了瓜吡啶吡啶生物碱卡那丁，鼠疫素D和鼠疫素G。合成中的关键步骤包括上述取代的吡啶甲基溴的烯醇烷基化和分子内Mizoroki-Heck反应形成目标化合物的七元碳环。
• An Agostic Iridium Pincer Complex as a Highly Efficient and Selective Catalyst for Monoisomerization of 1‐Alkenes to <i>trans</i> ‐2‐Alkenes
  作者：Yulei Wang、Chuan Qin、Xiangqing Jia、Xuebing Leng、Zheng Huang

  DOI：10.1002/anie.201611007

  日期：2017.2

  between the Ir and two σ C−H bonds from a tBu substituent, has been prepared. This complex exhibits exceptionally high activity and excellent regio‐ and stereoselectivity for monoisomerization of 1‐alkenes to trans‐2‐alkenes with wide functional‐group tolerance. Reactions can be performed in neat reactant on a more than 100 gram scale using 0.005 mol % catalyst loadings with turnover numbers up to 19000.

  制备了一种独特的Ir络合物（tBu NC C P）Ir，其中吡啶-膦钳夹为唯一配体，其特征在于Ir与来自t Bu取代基的两个σC-H键之间具有双重原子相互作用。该复合物具有极高的活性，并具有极好的区域和立体选择性，可将1烯烃单异构化为反式-2-烯烃，且具有宽泛的官能团耐受性。可以使用0.005 mol％的催化剂负载量（周转数高达19000）在超过100克的纯净反应物中进行反应。