2-(1-羟基-1-乙基)-3-丁烯酸乙酯 | 502684-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 2-(1-羟基-1-乙基)-3-丁烯酸乙酯
• 英文名称: Ethyl 2-(1-hydroxy-1-ethyl)-3-butenoate
• 英文别名: Ethyl 2-(1-hydroxyethyl)but-3-enoate
• CAS: 502684-94-8
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: ABLZHKCYUMBTSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-(1-羟基-1-乙基)-3-丁烯酸乙酯 在 碘 、 silver trifluoromethanesulfonate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以38%的产率得到2-Methyl-3-carbetoxy-4-iodotetrahydrofuran
  参考文献：
  名称：

  Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans

  摘要：

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.

  DOI：

  10.1021/jo00101a024
• 作为产物：
  描述：

  4-溴巴豆酸乙酯 、 乙醛 在 indium 、 水 作用下， 反应 192.0h， 生成 5-hydroxy-hex-2-enoic acid ethyl ester 、 2-(1-羟基-1-乙基)-3-丁烯酸乙酯 、 6-甲基-5,6-二氢-2H-吡喃-2-酮
  参考文献：
  名称：

  水介质中高度α-区域选择性金属介导的烯丙基化反应的发展：α-高烯丙醇起源的新机制建议

  摘要：

  本文描述了使用水中的铟、锌和锡获得 α-加合物高烯丙醇的一般方法。提出了一种新机制来解释这些合成上难以获得的分子的形成。通常，该方法可以使用各种醛和烯丙基卤化物进行，只需添加 6 当量的水，从而以高选择性得到 α-加合物。为了解释 α-高烯丙基醇的起源，使用 1H NMR、交叉实验和 22β γ-加合物高烯丙基甾醇转化为 22α α-加合物高烯丙基甾醇的立体化学研究仔细研究了反应机理。从机理研究结果来看，金属介导的α-区域选择性烯丙基化可能存在两种机制途径共存。

  DOI：

  10.1021/ja029276s

文献信息

• Cha, Joo Hwan; Pae, Ae Nim; Choi, Kyung Il Il, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 17, p. 2079 - 2081
  作者：Cha, Joo Hwan、Pae, Ae Nim、Choi, Kyung Il Il、Cho, Yong Seo、Koh, Hun Yeong、Lee, Eun

  DOI：——

  日期：——
• Development of a Highly α-Regioselective Metal-Mediated Allylation Reaction in Aqueous Media:  New Mechanistic Proposal for the Origin of α-Homoallylic Alcohols
  作者：Kui-Thong Tan、Shu-Sin Chng、Hin-Soon Cheng、Teck-Peng Loh

  DOI：10.1021/ja029276s

  日期：2003.3.1

  This paper described a general method to obtain α-adduct homoallylic alcohols using indium, zinc, and tin in water. A new mechanism was proposed to account for the formation of these synthetically difficult-to-obtain molecules. Generally, this method can be performed with a wide range of aldehydes and allylic halides with just 6 equiv of water added, giving the α-adduct in high selectivities. To account

  本文描述了使用水中的铟、锌和锡获得 α-加合物高烯丙醇的一般方法。提出了一种新机制来解释这些合成上难以获得的分子的形成。通常，该方法可以使用各种醛和烯丙基卤化物进行，只需添加 6 当量的水，从而以高选择性得到 α-加合物。为了解释 α-高烯丙基醇的起源，使用 1H NMR、交叉实验和 22β γ-加合物高烯丙基甾醇转化为 22α α-加合物高烯丙基甾醇的立体化学研究仔细研究了反应机理。从机理研究结果来看，金属介导的α-区域选择性烯丙基化可能存在两种机制途径共存。
• Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans
  作者：Paul Galatsis、Scott D. Millan、Patrik Nechala、George Ferguson

  DOI：10.1021/jo00101a024

  日期：1994.11

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.