2-propynyl cyclohexyl carbonate

• 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: 2-propynyl cyclohexyl carbonate
• 英文别名: Cyclohexyl prop-2-ynyl carbonate
• 化学式: C₁₀H₁₄O₃
• mdl: MFCD09030273
• 分子量: 182.219
• InChiKey: AQOMLQCSDBHFQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  炔丙基氯甲酸酯 、 环己醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到2-propynyl cyclohexyl carbonate
  参考文献：
  名称：

  Highly Selective Deblocking of Propargyl Carbonates in the Presence of Propargyl Carbamates with Tetrathiomolybdate

  摘要：

  Propargyloxycarbonyl chloride, 1, has been used to protect the hydroxyl and amino functionalities of amino alcohols and aminophenols in one pot using triethylamine or pyridine as a base. The increased reactivity of benzyltriethylammonium tetrathiomolybdate, 2, toward propargyl carbonates over propargyl carbamates is studied in detail and has been exploited further to develop an orthogonal protection strategy for the hydroxyl and amino functionalities. For example, 2-amino-1-butanol, 6a, was treated with 1 to get the N,O-diPoc compound 7a in 90% yield, which when treated with 1.1 equiv of 2 at room temperature removes the Poc group attached to oxygen while leaving the one attached to nitrogen intact to yield compound Sa in 85% yield. This particular observation offers a new protecting strategy where an amine and an alcohol group can be protected simultaneously in one pot, and in a later synthetic step, if the alcohol group has to be deprotected selectively, it can be achieved with 1 equiv of 2.

  DOI：

  10.1021/jo048777o

文献信息

• Highly Selective Deblocking of Propargyl Carbonates in the Presence of Propargyl Carbamates with Tetrathiomolybdate
  作者：R. Ramesh、Ramakrishna G. Bhat、Srinivasan Chandrasekaran

  DOI：10.1021/jo048777o

  日期：2005.2.1

  Propargyloxycarbonyl chloride, 1, has been used to protect the hydroxyl and amino functionalities of amino alcohols and aminophenols in one pot using triethylamine or pyridine as a base. The increased reactivity of benzyltriethylammonium tetrathiomolybdate, 2, toward propargyl carbonates over propargyl carbamates is studied in detail and has been exploited further to develop an orthogonal protection strategy for the hydroxyl and amino functionalities. For example, 2-amino-1-butanol, 6a, was treated with 1 to get the N,O-diPoc compound 7a in 90% yield, which when treated with 1.1 equiv of 2 at room temperature removes the Poc group attached to oxygen while leaving the one attached to nitrogen intact to yield compound Sa in 85% yield. This particular observation offers a new protecting strategy where an amine and an alcohol group can be protected simultaneously in one pot, and in a later synthetic step, if the alcohol group has to be deprotected selectively, it can be achieved with 1 equiv of 2.