methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate | 35066-34-3

• 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: methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate
• 英文别名: methyl (2E)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enoate；2-Pentenoic acid, 3-methyl-5-[(tetrahydro-2H-pyran-2-yl)oxy]-, methyl ester, (E)-；methyl (E)-3-methyl-5-(oxan-2-yloxy)pent-2-enoate
• CAS: 35066-34-3
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: JMMIHPBZZJDAQV-MDZDMXLPSA-N

物化性质

• 沸点：
  327.4±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 甲基磺酰氯 、 lithium chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 (2E)-1-chloro-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ene
  参考文献：
  名称：

  PtCl₂-Catalyzed Transannular Cycloisomerization of 1,5-Enynes:  A New Efficient Regio- and Stereocontrolled Access to Tricyclic Derivatives

  摘要：

  (GRAPHICS)Transannular PtCL2-catalyzed cycloisomerizations open a new route to cyclopropanic tricyclic systems. Ketones A or C were efficiently prepared from the same cycloundec-5-en-1-yne precursor B, depending on the substituent at the propargylic position (either benzoate or methoxy).

  DOI：

  10.1021/ol048463n
• 作为产物：
  描述：

  methyl 5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynoate 在 copper(I) bromide dimethylsulfide complex 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 7.5h， 生成 methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate
  参考文献：
  名称：

  PtCl₂-Catalyzed Transannular Cycloisomerization of 1,5-Enynes:  A New Efficient Regio- and Stereocontrolled Access to Tricyclic Derivatives

  摘要：

  (GRAPHICS)Transannular PtCL2-catalyzed cycloisomerizations open a new route to cyclopropanic tricyclic systems. Ketones A or C were efficiently prepared from the same cycloundec-5-en-1-yne precursor B, depending on the substituent at the propargylic position (either benzoate or methoxy).

  DOI：

  10.1021/ol048463n

文献信息

• Stoffwechselprodukte von Mikroorganismen. 101. Mitteilung. Synthese dertrans-5-Hydroxy-3-methylpenten-(2)-s�ure (trans-?2-Anhydromevalons�ure)
  作者：W. Keller-Schierlein、J. Widmer、B. Maurer

  DOI：10.1002/hlca.19720550123

  日期：1972.1.31

  trans-Δ2-Anhydromevalonic acid (XVII) was prepared by a Wittig reaction, starting from (4-tetrahydro-2-pyranyloxy)-2-butanone. On the other hand, the corresponding 4-acetoxy-2-butanone gave, under similar conditions, the cyclohexene derivative V, explainable by a twofold Michael addition of the Wittig reagent to methyl vinyl ketone, followed by an intramolecular alcol condensation.

  反式-Δ 2 -Anhydromevalonic酸（XVII）用制备维悌希反应，从（4-四氢-2-吡喃基）-2-丁酮开始。另一方面，在相似的条件下，相应的4-乙酰氧基-2-丁酮产生了环己烯衍生物V，这可以通过将Wittig试剂两次迈克尔加成到甲基乙烯基酮上，然后进行分子内醇缩合来解释。
• Synthesis of natural maleimides farinomaleins C–E and evaluation of their antifungal activity
  作者：Santosh Lahore、Sachin T. Aiwale、Paola Sardi、Sabrina Dallavalle

  DOI：10.1016/j.tetlet.2014.05.023

  日期：2014.7

  A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides. (C) 2014 Elsevier Ltd. All rights reserved.