8-(phenyl)oct-2-en-7-ynal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-(phenyl)oct-2-en-7-ynal
• 英文别名: (E)-8-phenyloct-2-en-7-ynal
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: BMPSEDBCWXXZJJ-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-(phenyl)oct-2-en-7-ynal 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl ((2E,4E)-10-phenyldeca-2,4-dien-9-yn-1-yl) carbonate
  参考文献：
  名称：

  钯催化的二烯基烯丙基碳酸酯的烯丙基胺的反阴离子控制的区域选择性

  摘要：

  通过磷酰胺-钯催化已经开发了区域选择性的Pd催化的二烯丙基烯丙基碳酸酯和芳族胺的烯丙基胺化反应。区域选择性可以通过π-烯丙基铝中间体的抗衡离子来改变。结果，通过调节反应条件，从相同的底物以高水平的区域选择性产生支链Z-二烯基烯丙基胺或线性共轭烯丙基胺。

  DOI：

  10.1016/j.tet.2021.131996

文献信息

• Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
  作者：Aireal D. Jenkins、Ananda Herath、Minsoo Song、John Montgomery

  DOI：10.1021/ja206722t

  日期：2011.9.14

  Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry

  已经开发了烯醛或烯酸酯与炔烃的还原环加成的策略。烯醛-炔环加成直接提供环戊烯醇，而烯酸酯-炔环加成提供类似的环戊烯酮。这些过程的机制可能涉及金属环中间体的形成和质子化。一般策略提供了从简单、稳定的 π 系统到五元环产品的直接入口。
• Structure of an η¹ Nickel <i>O</i>-Enolate:  Mechanistic Implications in Catalytic Enyne Cyclizations
  作者：Kande K. D. Amarasinghe、Sanjoy K. Chowdhury、Mary Jane Heeg、John Montgomery

  DOI：10.1021/om0010013

  日期：2001.2.1

  Two metallacycles derived from the oxidative cyclization of nickel(0) with an alkynyl enal have been isolated and fully characterized. The metallacycles obtained possess an η1 nickel O-enolate motif within the metallacyclic framework.

  分离并充分表征了衍生自镍（0）与炔基烯醛的氧化环化作用的两个金属环。得到的metallacycles具有一个η 1镍Ò -enolate基序中的metallacyclic框架内。
• Cascade Cyclizations and Couplings Involving Nickel Enolates
  作者：Gireesh M. Mahandru、Andy R. L. Skauge、Sanjoy K. Chowdhury、Kande K. D. Amarasinghe、Mary Jane Heeg、John Montgomery

  DOI：10.1021/ja037423w

  日期：2003.11.1

  A new strategy for effecting cascade cyclization processes using nickel enolates has been developed. Nickel enolates may be cleanly generated by the oxidative cyclization of an enal and alkyne with Ni(0), and the resulting enolate may be functionalized by a variety of alkylation processes. Partially and fully intramolecular versions of the process allow the rapid synthesis of complex polycyclics from simple achiral, acyclic precursors.
• Diverse Reactivity Manifolds of Alkynyl Enone- and Alkynyl Enal-Derived Nickelacycles:  Discovery of Nickel-Promoted [3+2] and [2+1] Cycloadditions
  作者：Sanjoy K. Chowdhury、Kande K. D. Amarasinghe、Mary Jane Heeg、John Montgomery

  DOI：10.1021/ja0012624

  日期：2000.7.1
• Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates
  作者：Meng-Lan Shen、Pu-Sheng Wang、Liu-Zhu Gong

  DOI：10.1016/j.tet.2021.131996

  日期：2021.3

  A regioselective Pd-catalyzed allylic amination reaction of dienyl allylic carbonates and aromatic amines has been developed by means of phosphoramidte-palladium catalysis. The regioselectivity could be altered by the counterion of the π-allylpalladium intermediate. As a result, either branched Z-dienyl allylic amines or linear conjugated allylic amines were generated in high levels of regioselectivity

  通过磷酰胺-钯催化已经开发了区域选择性的Pd催化的二烯丙基烯丙基碳酸酯和芳族胺的烯丙基胺化反应。区域选择性可以通过π-烯丙基铝中间体的抗衡离子来改变。结果，通过调节反应条件，从相同的底物以高水平的区域选择性产生支链Z-二烯基烯丙基胺或线性共轭烯丙基胺。