1-(2-phenylethynylcyclohex-1-enyl)-3-phenylpropyn-1-ol | 196407-34-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-(2-phenylethynylcyclohex-1-enyl)-3-phenylpropyn-1-ol
• CAS: 196407-34-8
• 化学式: C₂₃H₂₀O
• 分子量: 312.411
• InChiKey: PHBIWRZSYQNKNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethynylcyclohex-1-enyl)-3-phenylpropyn-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到1-(2-phenylethynylcyclohex-1-enyl)-3-phenylpropyn-1-one
  参考文献：
  名称：

  Ring Size and Substituent Effects in Oxyanion-Promoted Cyclizations of Enyne-allenes:  Observation of a Myers−Saito Cycloaromatization at Cryogenic Temperature

  摘要：

  A series of acetoxy-substituted enyne-allenes, fused to cyclopentene and cyclohexene ring systems, were synthesized and treated with methyllithium to generate the corresponding enolates. It was found that whereas the cyclohexannulated examples underwent either C-2-C-7 (Myers-Saito) cycloaromatization or C-2-C-6 (Schmittel) cyclization depending on their terminal subsituents, the cyclopentannulated examples either failed to cyclize altogether or underwent C-2-C-7 cyclization. Both of these results lie in contrast to the behavior of their benzannulated analogues, which underwent exclusive C-2-C-6 cyclization independent of substituents. These findings are rationalized on the basis of both ring strain effects and the steric encumbrance of the terminal alkynyl and allenyl subsituents.

  DOI：

  10.1021/jo061088n
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 1-(2-phenylethynylcyclohex-1-enyl)-3-phenylpropyn-1-ol
  参考文献：
  名称：

  Ring size effects in the C2–C6 biradical cyclisation of enyne–allenes and the relevance for neocarzinostatin

  摘要：

  烯炔醛 1 热环化反应的区域选择性可随环烯的环径大小而变化。以环戊烯作为烯分子时，会形成迈尔萨托（C2âC7）环芳香化产物，而以六元和七元环烯为烯分子时，则会出现新颖的 C2âC6 环化现象。DFT 计算用于合理解释这些变化。讨论了这些发现对新卡西诺司他汀的替代热双向环化反应的影响。

  DOI：

  10.1039/b102380m

文献信息

• Gold-Catalyzed Oxidative Cyclizations of {<i>o</i>-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1<i>H</i>-Isochromenes and 2<i>H</i>-Pyrans
  作者：Jidong Zhao、Wei Xu、Xin Xie、Ning Sun、Xiangdong Li、Yuanhong Liu

  DOI：10.1021/acs.orglett.8b02380

  日期：2018.9.7

  A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed

  基于金催化的邻-（炔基）苯基炔丙基醚衍生物的氧化环化反应，开发了一种新的方便的合成功能化的1 H-异戊二烯和2 H-吡喃衍生物的策略。该反应通过金催化的高度区域选择性氧化进行，然后进行烯键基的1，2-迁移和核苷加成。还通过氧化裂解所获得的1 H-异色酮的环外双键来构建异香豆素。
• Ring Strain Effects in Enyne-Allene Thermolysis: Switch from the Myers-Saito Reaction to the C2-C6 Biradical Cyclization
  作者：Michael Schmittel、Jens-Peter Steffen、Dominik Auer、Michael Maywald

  DOI：10.1016/s0040-4039(97)01393-2

  日期：1997.9

  The mode of the thermal cyclization of enyne-allenes 1 depends on ring strain effects: when the ene functionality is part of a benzene, cyclohexene or cycloheptene ring the novel C2-C6 biradical cyclization is observed, while when it is part of a cyclopentene ring the Myers-Saito cycloaromatization is registered. © 1997 Elsevier Science Ltd.

  烯炔-丙烯1的热环化模式取决于环应变效应：当烯官能团是苯，环己烯或环庚烯环的一部分时，观察到新型C 2 -C 6双自由基环化，而当它是a的一部分时Myers-Saito环芳环化反应的环戊烯环已注册。©1997爱思唯尔科学有限公司。