4-Methoxymethoxy-5-methyl-hex-2-ynoic acid ethyl ester | 128114-05-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-Methoxymethoxy-5-methyl-hex-2-ynoic acid ethyl ester
• 英文别名: Ethyl 4-(methoxymethoxy)-5-methylhex-2-ynoate
• CAS: 128114-05-6
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: NXVZJFSNOBYMEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  274.4±20.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 4-Methoxymethoxy-5-methyl-hex-2-ynoic acid ethyl ester 在 copper(I) bromide dimethylsulfide complex zinc(II) chloride 作用下， 生成 2-(1-Methoxymethoxy-2-methyl-propyl)-5-oxo-cyclopent-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Addition of zinc homoenolates to acetylenic esters and amides: a formal [3 + 2] cycloaddition

  摘要：

  The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.

  DOI：

  10.1021/jo00057a013

文献信息

• Addition of functionalized zinc copper reagents to acetylenic esters: Synthesis of 2-carboalkoxy cyclohexenones
  作者：Michael T. Crimmins、Sujuan Huang、Lisa E. Guise、D. Borden Lacy

  DOI：10.1016/0040-4039(95)01485-z

  日期：1995.9

  Conjugate addition of the zinc-copper reagent derived from ethyl 4-iodobutyrate to acetylenic esters in the presence of TMSCI and HMPA results in cyclization and formation of 3-alkyl-2-carboalkoxycyclohexenones in good yields.

  在TMSCI和HMPA存在下，将4-碘丁酸乙酯衍生的锌-铜试剂共轭添加到炔属酯中可导致环化并以高收率形成3-烷基-2-羰基烷氧基环己烯酮。
• Addition of zinc homoenolates to acetylenic esters: a formal [3+2] cycloaddition
  作者：Michael T. Crimmins、Philippe G. Nantermet

  DOI：10.1021/jo00301a003

  日期：1990.7
• CRIMMINS, MICHAEL T.;NANTERMET, PHILIPPE G., J. ORG. CHEM., 55,(1990) N4, C. 4235-4237
  作者：CRIMMINS, MICHAEL T.、NANTERMET, PHILIPPE G.

  DOI：——

  日期：——