5-acetoxy-2,4-pentadienal | 89639-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetoxy-2,4-pentadienal
• 英文别名: 5-Oxopenta-1,3-dien-1-yl acetate；5-oxopenta-1,3-dienyl acetate
• CAS: 89639-86-1
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: MNJXOYCVMUFRAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetoxy-2,4-pentadienal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-acetoxy-2,4-pentadien-1-ol
  参考文献：
  名称：

  Acyclic O- and N-substituted pentadienyl cations: Structural characterisation, cyclisation and computational results

  摘要：

  A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.

  DOI：

  10.1016/0040-4020(95)00369-j
• 作为产物：
  描述：

  吡啶 在 氯磺酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.42h， 生成 5-acetoxy-2,4-pentadienal
  参考文献：
  名称：

  10.1093/bulcsj/uoae055

  摘要：

  Abstract In this study, near-infrared absorbing rotaxane-type cyanine dyes exhibit high tolerance to various chemical reactions, which is attributed to the encapsulation effect of their cyclic molecules. As a result, rotaxane dyes can be post-modified on the host α-cyclodextrin or guest cyanine skeleton to adjust their solubility, absorption wavelength, stability, and singlet oxygen generation ability. The guest modification product obtained via the Heck reaction demonstrates a red shift of its absorption wavelength owing to the extended conjugation system. Moreover, the products of host modification through the methylation and benzylation of all cyclodextrin hydroxyl groups not only become lipophilic and show extended absorption, but also exhibit higher photooxidation tolerance, lower singlet oxygen generation rate, and increased singlet oxygen tolerance, indicating their potential applicability as highly durable dyes. Furthermore, the outstanding singlet oxygen tolerance of these dyes enables their use in long-life singlet oxygen generators, in which the total amount of singlet oxygen increases. This work demonstrates that an intrinsically unstable near-infrared cyanine dye can be used as a synthetic intermediate by stabilizing it via α-cyclodextrin encapsulation, allowing the post-modification of various properties of cyanine dyes toward the higher-order near-infrared-absorbing materials with complex functionalities and diverse utilities.

  DOI：

  10.1093/bulcsj/uoae055

文献信息

• A Complex Comprising a Cyanine Dye Rotaxane and a Porphyrin Nanoring as a Model Light‐Harvesting System
  作者：Jiratheep Pruchyathamkorn、William J. Kendrick、Andrew T. Frawley、Andrea Mattioni、Felipe Caycedo‐Soler、Susana F. Huelga、Martin B. Plenio、Harry L. Anderson

  DOI：10.1002/anie.202006644

  日期：2020.9.14

  A nanoring‐rotaxane supramolecular assembly with a Cy7 cyanine dye (hexamethylindotricarbocyanine) threaded along the axis of the nanoring was synthesized as a model for the energy transfer between the light‐harvesting complex LH1 and the reaction center in purple bacteria photosynthesis. The complex displays efficient energy transfer from the central cyanine dye to the surrounding zinc porphyrin nanoring

  合成了具有沿纳米环轴延伸的 Cy7 花青染料（六甲基吲哚三碳花青）的纳米环-轮烷超分子组装体，作为光捕获复合物 LH1 与紫色细菌光合作用反应中心之间能量转移的模型。该复合物表现出从中心花青染料到周围锌卟啉纳米环的有效能量转移。我们提出了一个理论模型，可以重现纳米环的吸收光谱并量化纳米环和中心染料之间的激子耦合，从而解释有效的能量转移并证明与结构相关的自然光捕获系统的相似性。
• Stabilisation of a heptamethine cyanine dye by rotaxane encapsulation
  作者：C. M. Simon Yau、Sofia I. Pascu、Susan A. Odom、John E. Warren、Eric J. F. Klotz、Michael J. Frampton、Charlotte C. Williams、Veaceslav Coropceanu、Marina K. Kuimova、David Phillips、Stephen Barlow、Jean-Luc Brédas、Seth R. Marder、Val Millar、Harry L. Anderson

  DOI：10.1039/b802728e

  日期：——

  The crystal structure of a cyanine dye rotaxane shows that the cyclodextrin is tightly threaded round the polymethine bridge of the dye; encapsulation dramatically increases the kinetic chemical stability of the radicals formed on oxidation and reduction of the dye, making it possible to observe the rotaxane radical dication by ESR and UV-vis-NIR spectroscopy.

  花青染料轮烷的晶体结构表明，环糊精紧密地绕着染料的聚次甲基桥。包封显着提高了染料氧化和还原时形成的自由基的动力学化学稳定性，从而可以通过ESR和UV-vis-NIR光谱观察轮烷的自由基指示。
• Strategies for remote enantiocontrol in chiral gold(<scp>iii</scp>) complexes applied to catalytic enantioselective γ,δ-Diels–Alder reactions
  作者：Jolene P. Reid、Mingyou Hu、Susumu Ito、Banruo Huang、Cynthia M. Hong、Hengye Xiang、Matthew S. Sigman、F. Dean Toste

  DOI：10.1039/d0sc00497a

  日期：——

  square planar gold(III) complexes to access enantioenriched products has rarely been applied in asymmetric catalysis. In this context, we report a mechanistic and synthetic investigation into the use of N-heterocyclic (NHC) gold(III) complexes in γ,δ-Diels–Alder reactions of 2,4-dienals with cyclopentadiene. The optimal catalyst bearing a unique 2-chloro-1-naphthyl substituent allowed efficient synthesis

  使用手性方形平面金（III）络合物来访问对映体富集的产品很少用于不对称催化中。在此背景下，我们报告了对N-杂环（NHC）金的使用的机理和综合研究（III）在2,4-二烯与环戊二烯的γ，δ-Diels-Alder反应中形成复合物。带有独特的2-氯-1-萘基取代基的最佳催化剂可以高产率，非对映和对映选择性有效合成功能丰富的碳环。使用从设计者参数采集平台获得的分子描述符，对催化剂和底物趋势的过渡态和多元线性回归（MLR）分析表明，有吸引力的非共价相互作用（NCI）是决定关键选择性的因素。这些分析表明，底物近端双键与催化剂芳族基团之间的假定π-π相互作用是高对映选择性的重要特征。
• Baumgarten, Chemische Berichte, 1924, vol. 57, p. 1624
  作者：Baumgarten

  DOI：——

  日期：——
• Acyclic O- and N-substituted pentadienyl cations: Structural characterisation, cyclisation and computational results
  作者：James A.S. Howell、Paula J. O'Leary、Paul C. Yates、Zeev Goldschmidt、Hugo E. Gottlieb、Daphna Hezroni-Langerman

  DOI：10.1016/0040-4020(95)00369-j

  日期：1995.6

  A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.