(R)-2-methylbut-3-yn-1-ol | 1536144-57-6

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: (R)-2-methylbut-3-yn-1-ol
• 英文别名: (2R)-2-methylbut-3-yn-1-ol
• CAS: 1536144-57-6
• 化学式: C₅H₈O
• 分子量: 84.1179
• InChiKey: QDLPJHIEFRSZJK-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-2-methylbut-3-yn-1-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-2-methylbut-3-yn-1-yl 7-hydroxyheptanoate
  参考文献：
  名称：

  Exo-Selective Reductive Macrocyclization of Ynals

  摘要：

  A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.

  DOI：

  10.1021/acs.orglett.5b00381

文献信息

• Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans
  作者：Fumiya Urabe、Shohei Miyamoto、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1021/ol403746r

  日期：2014.2.7

  A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O-H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetrahydrofurans and exhibits complete E-selectivity in the case of nonterminal alkynes.
• Exo-Selective Reductive Macrocyclization of Ynals
  作者：Hengbin Wang、Solymar Negretti、Allison R. Knauff、John Montgomery

  DOI：10.1021/acs.orglett.5b00381

  日期：2015.3.20

  A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.