2,3-diallyl-1,4-dihydrobenzoquinone | 7330-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-diallyl-1,4-dihydrobenzoquinone
• 英文别名: 2,3-diallylhydroquinone；2,3-diallyl-hydroquinone；3.6-Dihydroxy-1.2-diallyl-benzol；2,3-Diallyl-hydrochinon；1,4-Benzenediol, 2,3-di-2-propenyl-；2,3-bis(prop-2-enyl)benzene-1,4-diol
• CAS: 7330-76-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: PVIZWRAPKUMOGT-UHFFFAOYSA-N

物化性质

• 熔点：
  87-90 °C
• 沸点：
  336.1±37.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diallyl-1,4-dihydrobenzoquinone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到2,3-dipropyl-1,4-dihydrobenzoquinone
  参考文献：
  名称：

  Synthesis and antineoplastic activity of hydroquinone dialdehydes

  摘要：

  A number of hydroquinone dialdehydes and structurally related compounds were synthesized and tested for antineoplastic efficacy against transplanted murine tumors. 3,6-Dihydroxy-4,5-dimethylphthalaldehyde,3,6-dihydroxy-4,5-dipropylphthalaldehyde, and 3,6-dihydroxy-4,5-dimethylphthalaldehyde hemialdal tetraacetate significantly prolonged the survival time of mice bearing either Sarcoma 180, Ehrlich carcinoma, or adenocarcinoma 755 ascites tumors. In addition, these agents were cytotoxic to Sarcoma 180 cells in culture at concentrations in the range of 25-30 microM.

  DOI：

  10.1021/jm00180a009
• 作为产物：
  描述：

  对苯二酚 在 potassium carbonate 作用下， 生成 2,3-diallyl-1,4-dihydrobenzoquinone
  参考文献：
  名称：

  以克莱森重排和闭环复分解为关键步骤设计和合成新型螺旋桨。

  摘要：

  新型六环笼状化合物是通过克莱森重排和闭环复分解（RCM）的组合制备的。另外，格氏反应与RCM结合产生了复杂的六环笼状分子。

  DOI：

  10.1002/chem.200501366

文献信息

• Colorant compounds, intermediates, and compositions
  申请人：Connor M. Daniel

  公开号：US20060223993A1

  公开（公告）日：2006-10-05

  Colorants are disclosed that exhibit high color strength, bright shades, and high thermal stability. Such compounds have found application as colorants for polyethylene terephthalate (“PET”). Potential end uses include disperse dyes, non-warping pigments, decolorizable colorants, and the like. Compounds and methods for synthesis include benzodifuranone related compounds, benzene centered lactones, benzene centered lactams; benzene-centered thiolactones; naphthalene-centered lactones; naphthalene-centered lactams; naphthalene-centered thiolactones; anthraquinone-centered lactones; anthraquinone-centered lactams; anthraquinone-centered thiolactones; anthracene-centered lactones; anthracene-centered lactams; anthracene-centered thiolactones; hetero-aromatic-centered lactones; hetero-aromatic centered lactams and hetero-aromatic centered thiolactone compounds, and the like. Furthermore, resins such as PET or other polymeric resins containing the compounds are disclosed.

  揭示了具有高色彩强度、明亮色调和高热稳定性的着色剂。这些化合物已被应用作聚对苯二甲酸乙二醇酯（“PET”）的着色剂。潜在的最终用途包括分散染料、不变形颜料、可褪色的着色剂等。合成的化合物和方法包括苯二呋喃酮相关化合物、苯中心内酯、苯中心内酰胺；苯中心巯内酯；萘中心内酯；萘中心内酰胺；萘中心巯内酯；蒽醌中心内酯；蒽醌中心内酰胺；蒽醌中心巯内酯；蒽中心内酯；蒽中心内酰胺；蒽中心巯内酯；杂芳环中心内酯；杂芳环中心内酰胺和杂芳环中心巯内酯化合物等。此外，还揭示了含有这些化合物的PET或其他聚合物树脂。
• Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System
  作者：Sambasivarao Kotha、Subba Cheekatla、Darshan Mhatre

  DOI：10.1055/s-0036-1591726

  日期：2017.12

  preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult

  摘要 据报道，涉及原子经济过程（例如克莱森重排，Diels-Alder反应，[2 + 2]光环加成和闭环复分解（RCM））的许多结构有趣的氧化笼化合物的制备均是关键步骤。氧杂环丁烷环系首次以烯烃复分解为关键步骤引入笼型骨架中。在这里组装的这些笼式系统很难通过传统方法来准备。本文所述的合成序列开辟了通往包含杂原子的更高阶多环的新途径，而无需保护基团的参与。在格利雅（Grignard）添加过程中观察到的跨环环化和此处使用的RCM协议可能适用于生成未知的氧化笼系统。 据报道，涉及原子经济过程（例如克莱森重排，Diels-Alder反应，[2 + 2]光环加成和闭环复分解（RCM））的许多结构有趣的氧化笼化合物的制备均是关键步骤。氧杂环丁烷环系首次以烯烃复分解为关键步骤引入笼型骨架中。在这里组装的这些笼式系统很难通过传统方法来准备。本文所述的合成序列开辟了通往包含杂原子的更高阶多环的新途径，而无需
• Synthesis of functionalized cage propellanes and D3-Trishomocubanes via the ring-closing metathesis and acid-promoted rearrangement
  作者：Sambasivarao Kotha、Subba Rao Cheekatla

  DOI：10.1016/j.tet.2018.11.027

  日期：2019.1

  Several functionalized cage propellanes and D3-trishomocubanes containing spiro linkage have been reported starting with commercially available materials such as 1,4-hydroquinone and dicyclopentadiene. In this regard, Claisen rearrangement, Diels–Alder reaction (DA), ring-closing metathesis (RCM) and acid-promoted rearrangement have been used as key steps. The strategies described here, opens up new

  已经报道了几种带有螺环键的功能化笼状螺旋藻和D 3-三柔藻，从1，4-对苯二酚和二环戊二烯等市售材料开始。在这方面，克莱森重排，狄尔斯-阿尔德反应（DA），闭环易位（RCM）和酸促进重排已用作关键步骤。此处描述的策略为组装复杂的笼式系统提供了新的机会，而这些笼式系统很难通过常规方法来构造。重排过程中产生的碳正离子中间体在设计异常笼形系统中起着重要作用。通过单晶X射线衍射研究明确地确定了重排的笼状化合物的结构之一。
• Design and Synthesis of Novel Propellanes by Using Claisen Rearrangement and Ring-Closing Metathesis as the Key Steps
  作者：Sambasivarao Kotha、Mirtunjay Kumar Dipak

  DOI：10.1002/chem.200501366

  日期：2006.5.24

  Novel hexacyclic caged compounds are prepared by a combination of Claisen rearrangement and ring-closing metathesis (RCM). Additionally, a Grignard reaction in conjugation with RCM produced intricate hexacyclic caged molecules.

  新型六环笼状化合物是通过克莱森重排和闭环复分解（RCM）的组合制备的。另外，格氏反应与RCM结合产生了复杂的六环笼状分子。
• Combined Multiple Claisen Rearrangement and Ring-closing Metathesis as a Route to Naphthalene, Anthracene, and Anthracycline Ring Systems
  作者：Shital K. Chattopadhyay、Benoy K. Pal、Susama Maity

  DOI：10.1246/cl.2003.1190

  日期：2003.12

  A new route involving double Claisen rearrangement of a suitable 1,4-diallyloxyarene system followed by ring-closing metathesis of the resulting diene has been developed for the synthesis of various benzannulated cyclohexenes. An important demonstration of this methodology is the construction of the tetracyclic quinophenolic ring system of the clinically important anthracyclines.

  已经开发了一种新的路线，该路线涉及合适的 1,4-二烯丙氧基芳烃系统的双克莱森重排，然后是所得二烯的闭环复分解，用于合成各种苯并环己烯。这种方法的一个重要证明是临床上重要的蒽环类四环喹酚环系统的构建。

表征谱图