(1R,2R)-1-phenylethynyl-7-oxabicyclo[4.1.0]heptane | 853995-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2R)-1-phenylethynyl-7-oxabicyclo[4.1.0]heptane
• 英文别名: (1R,6R)-1-(phenylethynyl)-7-oxabicyclo[4.1.0]heptane；(1R,6R)-1-(2-phenylethynyl)-7-oxabicyclo[4.1.0]heptane
• CAS: 853995-05-8
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: IEKKOVKGAAEDKQ-ZIAGYGMSSA-N

物化性质

• 沸点：
  317.4±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-phenylethynyl-7-oxabicyclo[4.1.0]heptane 在 sodium azide 、 二异丁基氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  H或N置换取代前驱体由手性环氧化物合成手性环醇

  摘要：

  提供了用于将环烯烃转化为手性反式-β-取代的环烷醇或手性α-氨基酮的对映选择性序列的不同实例。

  DOI：

  10.1021/acs.orglett.8b02822
• 作为产物：
  描述：

  2-(环己烯-1-基)乙炔基苯 在 Shi's ketone 、 oxone||potassium monopersulfate triple salt 、 四丁基硫酸氢铵 、 potassium carbonate 、 溶剂黄146 、 disodium ethylenediamine tetraacetic acid 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以86%的产率得到(1R,2R)-1-phenylethynyl-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  H或N置换取代前驱体由手性环氧化物合成手性环醇

  摘要：

  提供了用于将环烯烃转化为手性反式-β-取代的环烷醇或手性α-氨基酮的对映选择性序列的不同实例。

  DOI：

  10.1021/acs.orglett.8b02822

文献信息

• Palladium-Catalyzed Three-Component Coupling of Propargylic Oxiranes, Phenols and Carbon Dioxide
  作者：Masahiro Yoshida、Masataka Ihara、Tomohiko Murao、Kenji Sugimoto

  DOI：10.1055/s-2007-967962

  日期：——

  (Z)-1-Phenoxyalkenyl-substituted cyclic carbonates have been produced from three-component coupling of propargylic oxiranes, phenols and carbon dioxide in the presence of palladium catalyst. The scope and limitations of this reaction have been ­examined by using various phenols and propargylic oxiranes. A plausible mechanism for the reaction is also proposed.

  (Z)-1-苯氧基烯基取代的环状碳酸酯是通过丙炔醇氧杂环烯、酚和二氧化碳在钯催化剂存在下的三组分耦合反应合成的。使用多种酚和丙炔醇氧杂环烯对该反应的适用范围和限制进行了研究。也提出了该反应的一个合理机制。
• Palladium-catalyzed coupling reaction of propargylic oxiranes with arylboronic acids in aqueous media
  作者：Masahiro Yoshida、Hirofumi Ueda、Masataka Ihara

  DOI：10.1016/j.tetlet.2005.07.134

  日期：2005.9

  A novel type of coupling reaction has been developed by the palladium-catalyzed reaction of propargylic oxiranes with arylboronic acids, in which anti-substituted 4-aryl-2,3-allenols were produced in a highly diastereoselective manner. A chiral-substituted allene has been synthesized from the reaction of a chiral propargylic oxirane without loss of the chirality.

  炔丙基环氧乙烷与芳基硼酸的钯催化反应已开发出新型的偶联反应，其中以高度非对映选择性的方式制备了抗取代的4-芳基-2,3-烯丙醇。从手性炔丙基环氧乙烷的反应合成了手性取代的烯，而没有手性的损失。
• Regioselective anti-addition of phenols to propargylic oxiranes by palladium(0) catalyst
  作者：Masahiro Yoshida、Yukio Morishita、Masataka Ihara

  DOI：10.1016/j.tetlet.2005.03.138

  日期：2005.5

  (Z)-Phenol-substituted alkenes were produced by the palladium(0)-catalyzed reaction of propargylic oxiranes with phenols. The regio- and stereoselective addition of phenols to alkynes occurs via the formation of p-propargyl- and p-allylpalladium complexes. The phenoxy-substituted enones were produced simultaneously depending on the reaction conditions. 2005 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Diastereoselective Coupling of Propargylic Oxiranes with Terminal Alkynes
  作者：Masahiro Yoshida、Maiko Hayashi、Kozo Shishido

  DOI：10.1021/ol070224n

  日期：2007.4.1

  A diastereoselective coupling of propargylic oxiranes with terminal alkynes has been developed with use of a palladium catalyst. The stereochemistries of the resulting 4-alkynyl-substituted 2,3-allenols have been altered depending on the palladium catalyst. An optically active anti-substituted allene was synthesized from the reaction of an enantiomerically enriched propargylic oxirane without loss of chirality.
• Rhodium-Catalyzed Diastereoselective Coupling of Propargylic Oxiranes with Arylboronic Acids in Water
  作者：Masahiro Yoshida、Maiko Hayashi、Kennosuke Matsuda、Kozo Shishido

  DOI：10.3987/com-08-s(f)24

  日期：——

  A diastereoselective coupling of propargylic oxiranes with arylboronic acids in aqueous condition is described. 4-Aryl-substituted 2,3-allenols having syn-geometries were selectively synthesized by the rhodium-catalyzed reactions in water.