2-乙炔基-2-甲基环氧乙烷 | 4090-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙炔基-2-甲基环氧乙烷
• 英文名称: 1-ethynyl-1-methyloxirane
• 英文别名: 2-Methyl-2-ethynyloxirane；2-ethynyl-2-methyloxirane；2-Ethinyl-propylenoxid；2-Aethinyl-2-methyl-oxiran
• CAS: 4090-48-6
• 化学式: C₅H₆O
• 分子量: 82.102
• InChiKey: FOEJSKSCKIOALZ-UHFFFAOYSA-N

物化性质

• 沸点：
  120-125 °C(Press: 754 Torr)
• 密度：
  0.8929 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2910900090

反应信息

• 作为反应物：
  描述：

  2-乙炔基-2-甲基环氧乙烷 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Kleijn, H.; Meijer, J.; Overbeek, G. C., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 3, p. 97 - 101

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-炔 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-乙炔基-2-甲基环氧乙烷
  参考文献：
  名称：

  Synthesis of Bioactive Speciosins G and P from Hexagonia speciosa

  摘要：

  The first total synthesis of speciosins P and G, previously isolated from Hexagonia speciosa, is reported. These compounds have been synthesized by Sonogashira coupling from readily available starting materials. Siccayne was also synthesized from the same starting material in two steps along with a number of other derivatives. The compounds were tested in the wheat coleoptile bioassay. The most active compound was the intermediate 18, followed by 29 and 17. The structural requirements for activity in these compounds are the presence of methoxy groups in the aromatic ring and a formyl or hydroxy group in the side chain.

  DOI：

  10.1021/np500341q

文献信息

• A new furan annelation reaction by the palladium-catalyzed reaction of 2-alkynyl carbonates or 2-(1-alkynyl)oxiranes with β-keto esters
  作者：Ichiro Minami、Masami Yuhara、Hiroyuki Watanabe、Jiro Tsuji

  DOI：10.1016/0022-328x(87)80052-9

  日期：1987.11

  A new furan annelation by the palladium-catalyzed reaction of 2-alkynyl carbonates with β-keto esters is described. The reaction proceeds under mild neutral conditions and hence unstable 3-alkylidene-2,3-dihydrofurans can be prepared in this way. Similarly, reaction of 2-(1-alkynyl)oxiranes with β-keto esters gives alkylidene furans.

  描述了通过碳酸2-炔基碳酸酯与β-酮酯的钯催化反应的新的呋喃脱嵌。反应在温和的中性条件下进行，因此可以以这种方式制备不稳定的3-亚烷基-2，3-二氢呋喃。类似地，使2-（1-炔基）氧杂环戊烷与β-酮酯反应，得到亚烷基呋喃。
• Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A
  作者：Jan Deska、Jan-E. Bäckvall

  DOI：10.1039/b912128p

  日期：——

  Crude Porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

  粗猪胰脂肪酶已成功用于轴向手性伯烯丙醇的动力学拆分，提供了非常高的对映选择性，E值大于200。这种简单的旋光性丙二烯的获取方法可用于真菌代谢产物的全合成（-）-三甲酚内酯A，使其具有明确的立体化学分配。
• Enantioselective Ring-Opening Reactions of Racemic Ethynyl Epoxides via Copper−Allenylidene Intermediates: Efficient Approach to Chiral β-Amino Alcohols
  作者：Gaku Hattori、Akiko Yoshida、Yoshihiro Miyake、Yoshiaki Nishibayashi

  DOI：10.1021/jo901064n

  日期：2009.10.16

  copper-catalyzed ring-opening reactions of racemic ethynyl epoxides with amines using (R)-DTBM-MeO-BIPHEP as a chiral ligand have been found to give the corresponding amino alcohols in high yields with up to 94% ee. The reaction is considered to proceed via copper−allenylidene complexes as key intermediates. This methodology may provide a novel synthetic approach to optically active amino alcohols, the structures

  已经发现使用（R）-DTBM-MeO-BIPHEP作为手性配体的外消旋乙炔基环氧化物与胺的对映选择性铜催化的开环反应以高收率得到相应的氨基醇，ee高达94％。该反应被认为是通过铜-亚烯基络合物作为关键中间体进行的。该方法可以为旋光性氨基醇提供新颖的合成方法，其结构广泛存在于许多天然产物，生物活性化合物和手性配体中。
• Preparation of unstable 3-alkylidene furans by the palladium-catalyzed reaction of α-alkynyl epoxides with β-keto esters
  作者：Ichiro Minami、Masami Yuhara、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)95798-8

  日期：——

  Palladium-catalyzed reaction of α-alkynyl epoxides with β-keto esters gives unstable 3-alkylidene-2,3-dihydrofuran-4-carboxylates. It can be carried out under mild neutral conditions, and offers a good preparative method for 3-alkylidene furans.

  钯催化的α-炔基环氧化物与β-酮酸酯的反应生成了不稳定的3-亚烷基-2,3-二氢呋喃-4-羧酸酯。它可以在温和的中性条件下进行，为3-亚烷基呋喃的制备提供了一种很好的方法。
• The synthesis of furans from acetylenic epoxides and diols
  作者：D. Miller

  DOI：10.1039/j39690000012

  日期：——

  Acetylenic αβ-epoxides react with dilute sulphuric acid and mercuric sulphate on heating to give furans in good yields; the reaction involves an internal hydration at a terminal acetylenic carbon atom. Under the influence of sulphuric acid alone, only small quantities of furans are formed; the major products are acetylenic diols. These have been shown to be probable intermediates in the formation of

  乙炔αβ-环氧化物在加热时与稀硫酸和硫酸汞反应生成呋喃，收率高。该反应涉及在末端炔碳原子上的内部水合。仅在硫酸的影响下，仅形成少量的呋喃。主要产品是炔二醇。已证明它们是呋喃形成中的可能中间体。当在乙醇存在下用稀硫酸处理环氧化物时，会形成炔二醇的单醚。炔属β γ -环氧化物也已表明，得到呋喃在用硫酸的硫酸汞-催化的反应。