tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)pyrrolidine-1-carboxylate | 1429122-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)pyrrolidine-1-carboxylate
• 英文别名: Tert-butyl 3-hydroxy-3-prop-2-ynylpyrrolidine-1-carboxylate；tert-butyl 3-hydroxy-3-prop-2-ynylpyrrolidine-1-carboxylate
• CAS: 1429122-66-6
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: IPIGSYOUTNWJFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)pyrrolidine-1-carboxylate 在 一氯化碘 、 水 、 碳酸氢钠 、 sodium sulfite 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 22.5h， 以0.217 g的产率得到(E)-2-(iodomethylene)-1-azabicyclo[2.2.1]heptan-4-ol hydrochloride
  参考文献：
  名称：

  Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols

  摘要：

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.

  DOI：

  10.1021/jo400077m
• 作为产物：
  描述：

  3-溴丙炔 、 1-叔丁氧碳基-3-吡咯烷酮 在 zinc/copper couple 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 甲苯 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)pyrrolidine-1-carboxylate 、 tert-butyl 3-hydroxy-3-(propa-1,2-dien-1-yl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols

  摘要：

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.

  DOI：

  10.1021/jo400077m

文献信息

• Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols
  作者：Thomas O. Painter、Jonathon R. Bunn、Frank J. Schoenen、Justin T. Douglas、Victor W. Day、Conrad Santini

  DOI：10.1021/jo400077m

  日期：2013.4.19

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.