tert-Butyl 6-iodo-2-hexynoate | 151860-30-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-Butyl 6-iodo-2-hexynoate
• 英文别名: Tert-butyl 6-iodohex-2-ynoate
• CAS: 151860-30-9
• 化学式: C₁₀H₁₅IO₂
• 分子量: 294.132
• InChiKey: FHZATLRVDYHCDV-UHFFFAOYSA-N

物化性质

• 沸点：
  307.7±25.0 °C(predicted)
• 密度：
  1.476±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-Butyl 6-iodo-2-hexynoate 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl cyclobutylideneacetate
  参考文献：
  名称：

  Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters

  摘要：

  The lithium-iodine exchange-initiated intramolecular conjugate addition reactions of some model gamma-iodo-alpha,beta-acetylenic esters have been examined. Product mixtures arising from proton abstraction reactions were observed in reactions leading to 5-membered ring formation. More efficient cyclizations resulted when reactions were conducted in the presence of trimethylsilyl chloride to trap intermediate allenolate ions. Allenolate ion trapping by an internal electrophilic center in 26 resulted in the highly efficient formation of bicyclic ester 27.

  DOI：

  10.1021/jo00076a053
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 19.25h， 生成 tert-Butyl 6-iodo-2-hexynoate
  参考文献：
  名称：

  Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters

  摘要：

  The lithium-iodine exchange-initiated intramolecular conjugate addition reactions of some model gamma-iodo-alpha,beta-acetylenic esters have been examined. Product mixtures arising from proton abstraction reactions were observed in reactions leading to 5-membered ring formation. More efficient cyclizations resulted when reactions were conducted in the presence of trimethylsilyl chloride to trap intermediate allenolate ions. Allenolate ion trapping by an internal electrophilic center in 26 resulted in the highly efficient formation of bicyclic ester 27.

  DOI：

  10.1021/jo00076a053

文献信息

• Synthesis of Fused Tricyclic Amines Bearing Tetrasubstituted Carbons Using an Alkylation–Cyclization–Isomerization–3-aza-Cope Cascade Reaction
  作者：Takeo Sakai、Tomoki Furuhata、Kota Hosoe、Kaho Umemura、Yuji Mori

  DOI：10.1021/acs.orglett.3c00778

  日期：2023.5.5

  A new cascade reaction sequence that involves alkylation, cyclization, isomerization, and 3-aza-Cope rearrangement was discovered. The stereogenic centers of the starting piperidines were transferred to the bicyclic enamine products, and a range of electron-withdrawing groups on the alkyne moieties, from ketones to amides, were tolerated under the reaction conditions. The bicyclic enamines underwent

  发现了涉及烷基化、环化、异构化和 3-aza-Cope 重排的新级联反应序列。起始哌啶的立体异构中心被转移到双环烯胺产物上，并且在反应条件下可以容忍炔烃部分上的一系列吸电​​子基团，从酮到酰胺。双环烯胺经过三氟乙酸 (TFA) 介导的环化形成带有四取代碳的三环胺。