6-乙基-6-羟基辛酸甲酯 | 117771-54-7

• 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: 6-乙基-6-羟基辛酸甲酯
• 中文别名: 辛酸,6-乙基-6-羟基-,甲基酯
• 英文名称: methyl 6-ethyl-6-hydroxyoctanoate
• 英文别名: Methyl 6-ethyl-6-hydroxyoctanoate
• CAS: 117771-54-7
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: NRZDFGLWUDUWER-UHFFFAOYSA-N

物化性质

• 沸点：
  265.5±23.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-乙基-6-羟基辛酸甲酯 在 氘代甲醇-d 、 氢气 、 sodium hydride 作用下， 生成
  参考文献：
  名称：

  Bifunctional even-electron ions. III. Fragmentation behaviour of aliphatic hydroxonium ions containing an additional carbomethoxy group

  摘要：

  AbstractThe primary and subsequent fragmentations of the bifunctional oxonium ions \documentclass{article}\pagestyle{empty}\begin{document}${\rm R} \!-\! \mathop {\rm C}\limits^ + ({\rm OH})\! -\! ({\rm CH}_2)_n \! - \! {\rm COOCH}_3 $\end{document} (n = 0−5), a, are dominated by functional group interactions. Loss of CH3OH is the only appreciable primary fragmentation of the higher homoiogues, but for the lowest homologue (a0) this reaction is missing. Instead, CO loss is observed. The next homologue (a1) shov.s loss of CH2CO besides loss of CH3OH. The mode of the subsequent fragmentations is dependent on the chain length separating the functional group, and formation of cyclic ions is typical of the fragmentation behaviour of a2 and a3. Evidence for proton transfer from the carbonyl oxygen to the methoxy group of a protonated ester group is presented.

  DOI：

  10.1002/oms.1210230202
• 作为产物：
  描述：

  5-氯戊腈 在 4,4'-二叔丁基苯并 、 氢气 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 6-乙基-6-羟基辛酸甲酯
  参考文献：
  名称：

  掩蔽的β-，γ-和δ-锂酯烯酸酯：有机合成中有用的试剂

  摘要：

  ω氯原酸酯的反应1与锂和4,4'-二-催化量叔在不同亲电[卜的存在-butylbiphenyl（DTBB，5％摩尔）吨CHO，苯甲醛，（CH 2）5在−78°C下的THF中，CO，Et 2 CO，PhCOMe，PhCHNPh，Me 3 SiCl]在水解和酸催化的甲醇分解后，会生成官能化的甲酯2。在氯代三甲基硅烷的情况下，分离出羟乙基酯2'。该反应也适用于双环原酸酯3：而β-氯衍生物和羰基化合物直接生成γ-内酯4 水解后，相应的γ-氯衍生物在甲醇分解后可提供预期的甲酯。

  DOI：

  10.1016/s0040-4039(00)02172-9

文献信息

• Masked ω-Lithio Ester Enolates: Synthetic Applications
  作者：Miguel Yus、Rosario Torregrosa、Isidro Pastor

  DOI：10.3390/90500330

  日期：——

  The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4’-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ- lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.

  通过锂和催化量（5%摩尔）的DTBB（4,4'-二叔丁基联苯）进行锂化反应的协议，应用于ω-氯代原酸酯6在Barbier型条件下，经最终酸催化的甲醇分解反应，得到相应的功能化酯8或9（以氯三甲基硅烷为亲电试剂），或经过原酸酯脱保护和酸催化处理，得到δ-内酯11。该方法也适用于双环原酸酯14：β-氯代OBO酯衍生物产生γ-内酯15，而γ-氯代OBO酯则得到相应的酯8。
• Bifunctional even-electron ions. IV. Fragmentation behaviour of aliphatic methoxonium ions containing an additional carbomethoxy group
  作者：U. I. Záhorszky、P. Schulze

  DOI：10.1002/oms.1210230203

  日期：1988.2

  AbstractAs for the corresponding hydroxonium ions, the methoxonium ions \documentclassarticle}\pagestyleempty}\begindocument}$\rm R} \!-\! \mathop \rm C}\limits^ + (\rm OCH}_2)\! -\! (\rm CH}_2)_n \! - \! \rm COOCH}_3 $\enddocument} (n = 0−5), b, show as the main reactions those triggered by functional group interaction, but the overall decomposition rate is not much influenced. Loss of CH3OH is the general primary fragmentation, originating preferentially from the COOCH3 group. The lowest homologue (b0) shows loss of C3H4O as the main primary reaction, while b1 shows loss of CH2CO besides CH3OH loss. The subsequent fragmentations exhibit strong chain‐length dependence. Methoxy anion migration is observed as a general reaction mode of fragment ions which still contain the COOCH3 group. The fragmentation behaviour of a and b and of the corresponding methoxy‐substituted bifunctional ions has been compared, and general conclusions have been drawn.
• Masked β-, γ- and δ-lithium ester enolates: useful reagents in organic synthesis
  作者：Isidro M Pastor、Miguel Yus

  DOI：10.1016/s0040-4039(00)02172-9

  日期：2001.2

  acid-catalysed methanolysis, to functionalised methyl esters 2. In the case of chlorotrimethylsilane, hydroxyethyl esters 2′ are isolated. The reaction is also applied to bicyclic orthoesters 3: whereas β-chloro derivatives and carbonyl compounds gives directly γ-lactones 4 after hydrolysis, the corresponding γ-chloro derivative affords the expected methyl esters after methanolysis.

  ω氯原酸酯的反应1与锂和4,4'-二-催化量叔在不同亲电[卜的存在-butylbiphenyl（DTBB，5％摩尔）吨CHO，苯甲醛，（CH 2）5在−78°C下的THF中，CO，Et 2 CO，PhCOMe，PhCHNPh，Me 3 SiCl]在水解和酸催化的甲醇分解后，会生成官能化的甲酯2。在氯代三甲基硅烷的情况下，分离出羟乙基酯2'。该反应也适用于双环原酸酯3：而β-氯衍生物和羰基化合物直接生成γ-内酯4 水解后，相应的γ-氯衍生物在甲醇分解后可提供预期的甲酯。
• Bifunctional even-electron ions. III. Fragmentation behaviour of aliphatic hydroxonium ions containing an additional carbomethoxy group
  作者：U. I. Záluorszky

  DOI：10.1002/oms.1210230202

  日期：1988.2

  AbstractThe primary and subsequent fragmentations of the bifunctional oxonium ions \documentclassarticle}\pagestyleempty}\begindocument}$\rm R} \!-\! \mathop \rm C}\limits^ + (\rm OH})\! -\! (\rm CH}_2)_n \! - \! \rm COOCH}_3 $\enddocument} (n = 0−5), a, are dominated by functional group interactions. Loss of CH3OH is the only appreciable primary fragmentation of the higher homoiogues, but for the lowest homologue (a0) this reaction is missing. Instead, CO loss is observed. The next homologue (a1) shov.s loss of CH2CO besides loss of CH3OH. The mode of the subsequent fragmentations is dependent on the chain length separating the functional group, and formation of cyclic ions is typical of the fragmentation behaviour of a2 and a3. Evidence for proton transfer from the carbonyl oxygen to the methoxy group of a protonated ester group is presented.