methyl (1-(3-oxoprop-1-yn-1-yl)cyclohexyl)carbonate | 1360733-29-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: methyl (1-(3-oxoprop-1-yn-1-yl)cyclohexyl)carbonate
• 英文别名: Methyl [1-(3-oxoprop-1-ynyl)cyclohexyl] carbonate；methyl [1-(3-oxoprop-1-ynyl)cyclohexyl] carbonate
• CAS: 1360733-29-4
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: JQRRAXXPTSTSJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1-(3-oxoprop-1-yn-1-yl)cyclohexyl)carbonate 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 碳酸氢钠 、 N-氟代双苯磺酰胺 、 三乙胺 作用下， 以 氘代氯仿 为溶剂， 反应 60.0h， 生成 ethyl 3-cyclohexylidene-2-fluoro-3-(phenylthio)propanoate
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615
• 作为产物：
  描述：

  在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到methyl (1-(3-oxoprop-1-yn-1-yl)cyclohexyl)carbonate
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615

文献信息

• <i>N</i>-Heterocyclic Carbene-Catalyzed Internal Redox Reaction of Alkynals: An Efficient Synthesis of Allenoates
  作者：Yu-Ming Zhao、Yik Tam、Yu-Jie Wang、Zigang Li、Jianwei Sun

  DOI：10.1021/ol300111m

  日期：2012.3.16

  An efficient N-heterocyclic carbene (NHC)-catalyzed internal redox reaction of alkynals that bear a y leaving group has been developed. This process provides a new access to a range of allenoates in good yields. Preliminary results demonstrate that the enantioselective variant can also be achieved.
• α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals
  作者：Xu Wang、Zijun Wu、Jian Wang

  DOI：10.1021/acs.orglett.5b03615

  日期：2016.2.5

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.