2-(1-乙氧基乙氧基)丁腈 | 98355-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(1-乙氧基乙氧基)丁腈
• 英文名称: 2-(1-Ethoxyethoxy)butyronitrile
• 英文别名: 2-(1-Ethoxyethoxy)butanenitrile
• CAS: 98355-33-0
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: ZTRNLMFWGZGTCI-UHFFFAOYSA-N

物化性质

• 沸点：
  203.3±20.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-乙氧基乙氧基)丁腈 以65%的产率得到
  参考文献：
  名称：

  HIYAMA, TAMEJIRO;OISHI, HARUHITO;SAIMOTO, HIROYUKI, TETRAHEDRON LETT., 1985, 26, N 20, 2459-2462

  摘要：

  DOI：
• 作为产物：
  描述：

  丙醛扁桃腈 、 乙烯基乙醚 反应 1.5h， 以75.1%的产率得到2-(1-乙氧基乙氧基)丁腈
  参考文献：
  名称：

  Hajicek, Josef; Trojanek, Jan, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1262 - 1271

  摘要：

  DOI：

文献信息

• Synthesis of 4-Amino-2(5<i>H</i>)-furanones through Intra- and Intermolecular Nitrile Addition of Ester Enolates. Construction of Carbon Framework of an Antitumor Antibiotic Basidalin
  作者：Tamejiro Hiyama、Haruhito Oishi、Yukari (nee Kusano) Suetsugu、Kiyoharu Nishide、Hiroyuki Saimoto

  DOI：10.1246/bcsj.60.2139

  日期：1987.6

  ester group, deprotection, olefin isomerization and lactonization all in a single operation. The other is base-induced ringclosure of α-acyloxy nitriles. The two methods are applied to construction of the carbon framework of an antitumor antibiotic basidalin.

  公开了 4-氨基-2(5H)-呋喃酮的两条新路线。一种是基于乙酸叔丁酯或丙酸叔丁酯的烯醇镁与 O-保护的氰醇的反应，然后进行酸处理，在单一操作中实现酯基的水解、脱保护、烯烃异构化和内酯化。另一种是α-酰氧基腈的碱诱导环合。这两种方法均应用于构建抗肿瘤抗生素basidalin的碳骨架。
• Allyl cation stereochemistry in the intramolecular 4+3 cycloaddition reaction
  作者：Michael Harmata、Chandra B. Gamlath、Charles L. Barnes

  DOI：10.1016/s0040-4039(00)98008-0

  日期：1990.1

  Initial allyl cation geometry appears to be irrelevant with respect to the stereochemistry of cycloadducts in the intramolecular 4+3 cycloaddition of alkoxyallylic cations derived from alkoxyallylic sulfones.

  相对于衍生自烷氧基烯丙基砜的烷氧基烯丙基阳离子的分子内4 + 3环加成中的环加合物的立体化学，初始烯丙基阳离子的几何形状似乎无关紧要。
• Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation
  作者：Clayton H. Heathcock、Charles T. Buse、William A. Kleschick、Michael C. Pirrung、John E. Sohn、John Lampe

  DOI：10.1021/jo01294a030

  日期：1980.3
• 2-METHYL-2-(TRIMETHYLSILOXY)PENTAN-3-ONE
  作者：Young, Steven D.、Buse, Charles T.、Heathcock, Clayton H.

  DOI：10.15227/orgsyn.063.0079

  日期：——
• Intramolecular [4+3] Cycloadditions. Studies of Relative Asymmetric Induction
  作者：Michael Harmata、Chandra B. Gamlath、Charles L. Barnes、Darin E. Jones

  DOI：10.1021/jo00121a028

  日期：1995.8

  Treatment df both the E and Z isomers of alkoxyallylic sulfones 20a and 20b with TiCl4 results in the formation of 4 + 3 cycloadducts by intramolecular cycloaddition. The distribution of diastereomers is different from each isomer of educt. This suggests that cycloaddition occurs faster than any isomerization process of the intermediate allylic cations. Both the E and Z isomers of 20c lead to the same 4 + 3 cycloadduct with essentially complete diastereoselectivity. Inherently high simple diastereoselection and a strong conformational bias in the allylic cation intermediates for both isomers account for this selectivity. The importance of allylic cation stereochemistry in these reactions is underscored by the cyclization of 20d. The Z isomer give only 4 + 3 cycloadducts with excellent relative but poor simple diastereoselection, suggestive of a concerted reaction. The E isomer give a [3 + 2] cycloadduct, enol ether 60, as the major cycloadduct as well as 4 + 3 cycloadducts and chloride-trapping product 61. This result is indicative of a stepwise reaction. The data reflect the importance of allylic cation stereochemistry in the regiochemical and stereochemical outcomes of intramolecular 4 + 3 cycloaddition reactions.