6-(苄氧基)己-3-炔-1-醇 | 1020401-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(苄氧基)己-3-炔-1-醇
• 英文名称: 6-(benzyloxy)hex-3-yn-1-ol
• 英文别名: 6-benzyloxy-hex-3-yn-1-ol
• CAS: 1020401-70-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: MJZLRFBRRBKIKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(苄氧基)己-3-炔-1-醇 在 吡啶 、 甲酸 、 氯磺酰异氰酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到6-Phenylmethoxyhex-3-ynyl sulfamate
  参考文献：
  名称：

  Catalytic Metallonitrene/Alkyne Metathesis: A Powerful Cascade Process for the Synthesis of Nitrogen-Containing Molecules

  摘要：

  A conceptually novel metallonitrene/alkyne metathesis cascade reaction has been developed for the construction of nitrogen-containing compounds from simple alkyne starting materials. Rhodium(II) tetracarboxylate salts are efficient catalysts for this reaction, in which an electrophilic rhodium nitrene is trapped by an alkyne, resulting in the formation of a new C-N bond and the generation of a reactive metallocarbene for cascade reaction. The reaction is tolerant of both alkyl and aryl substituents on the alkyne, and proceeds at room temperature in a variety of common solvents. The modular nature of the reaction allows for the rapid construction of congested bicyclic systems from remarkably simple alkyne starting materials.

  DOI：

  10.1021/ja7111788
• 作为产物：
  描述：

  1,3,2-二噁唑噻吩-2,2-二氧化物 、 ((but-3-yn-1-yloxy)methyl)benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.58h， 以66%的产率得到6-(苄氧基)己-3-炔-1-醇
  参考文献：
  名称：

  Intramolecular Kulinkovich–de Meijere reactions of various disubstituted alkenes bearing amide groups

  摘要：

  A range of amides fitted with (E) or (Z) disubstituted alkene groups were prepared and evaluated in intramolecular Kulinkovich-de Meijere reactions. The corresponding aminocyclopropanes were obtained with high diastereoselectivity. Good yields could be achieved with substrates bearing suitable substitutions at the olefin moieties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.067

文献信息

• Asymmetric Total Synthesis of (+)-Attenol B
  作者：Jingyun Ren、Jian Wang、Rongbiao Tong

  DOI：10.1021/acs.orglett.5b00038

  日期：2015.2.6

  spiroketal attenol A and synthesized previously as a minor product. Herein, we report a new strategy that for the first time led to asymmetric synthesis of (+)-attenol B as an exclusive product, featuring sequential Achmatowicz rearrangement/bicycloketalization to efficiently construct the 6,8-dioxabicyclo[3.2.1]octane core. In addition, (−)-attenol A was obtained with 91% yield by isomerization of (+)-attenol

  分离出具有更高细胞毒性，热力学上较不稳定的（+）-萜烯醇B，将其作为螺旋酮Attenol A的次要异构体，并先前以次要产物的形式进行合成。在本文中，我们报告了一种新策略，该策略首次导致作为专有产品的（+）-Atenol B的不对称合成，其特征是顺序进行Achmatowicz重排/双环缩酮化，以有效地构建6,8-二氧杂双环[3.2.1]辛烷核。另外，（ - ） -在CDCl attenol乙-用产率的（+）异构化91％获得attenol甲3。