2-allyl-3-allyloxy-4-methoxy-benzaldehyde | 863659-43-2

• 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: 2-allyl-3-allyloxy-4-methoxy-benzaldehyde
• 英文别名: 2-allyl-3-allyloxy-4-methoxybenzaldehyde；4-Methoxy-3-prop-2-enoxy-2-prop-2-enylbenzaldehyde
• CAS: 863659-43-2
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: BEQCTSUKTJCTKC-UHFFFAOYSA-N

物化性质

• 沸点：
  347.9±37.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-3-allyloxy-4-methoxy-benzaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 [RuHCl(CO)(PPh₃)₃] 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 7-methoxybenzofuran-4-carbaldehyde
  参考文献：
  名称：

  An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

  摘要：

  Twelve substituted benzofurans were synthesized from their corresponding substituted l-allyl-2-allyloxybenzenes using ruthenium-mediated G and O-allyl isomerization followed by ring-closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.090
• 作为产物：
  描述：

  3-烯丙氧基-4-甲氧基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2-allyl-3-allyloxy-4-methoxy-benzaldehyde
  参考文献：
  名称：

  An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

  摘要：

  Twelve substituted benzofurans were synthesized from their corresponding substituted l-allyl-2-allyloxybenzenes using ruthenium-mediated G and O-allyl isomerization followed by ring-closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.090

文献信息

• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES, À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2011015241A1

  公开（公告）日：2011-02-10

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT2B (5-HT2B receptor), and on the prostaglandin F2 • receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30元大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，详细描述在说明书和专利要求中。I型大环可通过并行合成或组合化学方法轻松制备。它们设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-羟色胺受体亚型5-HT2B(5-HT2B受体)和前列腺素F2•受体(FP受体)上显示激动或拮抗活性。因此，它们潜在用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120270881A1

  公开（公告）日：2012-10-25

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of formulae Ia and Ib are constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. These macrocycles Ia and Ib are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being the agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), ion channels and signal transduction pathways. In particular, these macrocycles act as antagonists of the motilin receptor, the FP receptor and the purinergic receptors P2Y 1 , as modulators of the serotonin receptor of subtype 5-HT 2B , as blockers of the voltage-gated potassium channel K v 1.3 and as inhibitors of the β-catenin-dependent “canonical” Wnt pathway. Thus they are showing great potential as medicaments for a variety of diseases.

  具有结构限制的、空间定义的12-30环的大环系统Ia和Ib由三个不同的分子部分构成：模板A、构象调节剂B和桥C。这些大环Ia和Ib可以通过并行合成或溶液中或固相上的组合化学来轻松制备。它们被设计用于与各种特定的生物靶标类相互作用，例如对G蛋白偶联受体（GPCRs）、离子通道和信号转导途径的激动或拮抗活性。特别地，这些大环作为莫蒂林受体的拮抗剂、FP受体和嘌呤受体P2Y1的调节剂、5-HT2B亚型的5-羟色胺受体的调节剂、电压门控钾通道Kv1.3的阻断剂以及β-连环蛋白依赖的“经典”Wnt途径的抑制剂。因此，它们显示出作为各种疾病药物的巨大潜力。
• Domino cyclocondensation of arylaldehydes with 2-acetylpyridine
  作者：Meng-Yang Chang、Ming-Hao Wu

  DOI：10.1016/j.tet.2012.09.048

  日期：2012.11

  cyclohexane skeleton 3 was developed via the one-pot domino Claisen–Schmidt condensation reaction/Michael addition/double aldol reaction of 1 equiv of functionalized arylaldehyde 1 with 3 equiv of 2-acetylpyridine (2a).

  用于制备环己烷骨架的新的合成路线3是经由一锅煮多米诺克莱森-施密特缩合反应/迈克尔加成/双羟醛1个当量官能化的芳基醛中的反应产生1与3当量2-乙酰（的图2a）。
• Synthesis of benzodioxepanes
  作者：Meng-Yang Chang、Ming-Hao Wu、Tein-Wei Lee

  DOI：10.1016/j.tet.2012.05.063

  日期：2012.8

  Four benzodioxepanes 1a-1d were prepared from reaction of 4-methoxy-3-hydroxybenzaldehyde 4 via a series of reasonable transformations, including the regioselective PhBCl2-mediated double allylation of 4, one-pot combination of ring-closing metathesis of skeleton 3 and Baeyer-Villiger reaction, O-allylation of skeleton 2, Claisen rearrangement of skeleton 5, and one-pot combination of ring-closing metathesis and hydrogenation. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 1-Indanonyl Oxepanes
  作者：Meng-Yang Chang、Nien-Chia Lee

  DOI：10.1055/s-0031-1290304

  日期：2012.4

  A variety of 1-indanonyl oxepanes with the novel structure of indanonyl oxepanes was prepared from reaction of hydroxy-benzaldehydes via a series of reasonable transformations, including the regioselective PhBCl2-mediated allylation (or Claisen rearrangement), one-pot reaction of ring-closing metathesis and the Wittig olefination, hydrogenation, and the Friedel-Crafts intramolecular cyclization.