O-allyl-sesamol | 19202-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: O-allyl-sesamol
• 英文别名: 5-(allyloxy)benzo[d][1,3]dioxole；allyl 3,4-methylenedioxyphenyl ether；5-allyloxy-1,3-benzodioxole；1,3-Benzodioxole, 5-(2-propenyloxy)-；5-prop-2-enoxy-1,3-benzodioxole
• CAS: 19202-22-3
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD25960535
• 分子量: 178.188
• InChiKey: LALKONKNNIUATM-UHFFFAOYSA-N

物化性质

• 沸点：
  257.7±9.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-allyl-sesamol 在 dimethyl sulfide borane 、 lithium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 52.0h， 生成 1-[3-(3,4-亚甲基二氧基苯氧基)丙基]-4-苯基哌嗪马来酸盐
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032
• 作为产物：
  描述：

  3,4-Methylendioxy-phenyl-formiat 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 5.03h， 生成 O-allyl-sesamol
  参考文献：
  名称：

  不对称乙醇酸酯烷基化法合成8-O.6'和8-O.4'-新木质素

  摘要：

  已经优化了用于8-O.6'和8-O.4'-新木质素的全合成的乙醇酸酯烷基化方法，从而为天然产物提供了高总收率和出色的立体选择性。所开发的方法可以进一步用于合成许多天然和非天然的新木脂素。这是使用不对称乙醇酸酯烷基化方法合成新木脂素的第一种方法。

  DOI：

  10.1016/j.tetlet.2016.11.087

文献信息

• A New Artificial Cyclase for Polyprenoids:  Enantioselective Total Synthesis of (−)-Chromazonarol, (+)-8-<i>e</i><i>pi</i>-Puupehedione, and (−)-11‘-Deoxytaondiol Methyl Ether
  作者：Hideaki Ishibashi、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1021/ja0472026

  日期：2004.9.1

  pure 3-o-fluorobenzyloxy-2-hydroxy-2'-(p-methoxybemzyl)-1,1'-binaphthyl.SnCl4, which is effective for the enantioselective cyclization of 2-(polyprenyl)phenol derivatives to afford polycyclic terpenoids bearing a chroman skeleton such as (-)-chromazonarol, (+)-8-epi-puupehedione, a key synthetic intermediate of (+)-wiedendiol, and (-)-11'-deoxytaondiol methyl ether.

  本文介绍了一种新型人工环化酶，光学纯的 3-o-fluorobenzyloxy-2-hydroxy-2'-(p-methoxybemzyl)-1,1'-binaphthyl.SnCl4，可有效地对映选择性环化 2-(polyprenyl ) 苯酚衍生物，提供带有色满骨架的多环萜类化合物，例如 (-)-chromazonarol、(+)-8-epi-puupehedione、(+)-wiedendiol 的关键合成中间体和 (-)-11'-deoxytaondiolmethyl醚。
• A concise synthesis of carpanone using solid-supported reagents and scavengers
  作者：Ian R. Baxendale、Ai-Lan Lee、Steven V. Ley

  DOI：10.1039/b203388g

  日期：2002.8.8

  Polymer-supported reagents have been applied to the synthesis of the natural product carpanone resulting in a clean and efficient synthesis without the requirement for conventional purification techniques. A new polymer-supported transition metal isomerisation catalyst is also reported.

  聚合物辅助试剂已用于天然产物的合成 甲酮 无需常规操作即可进行清洁高效的合成 纯化技术。一个新的聚合物支持的过渡金属异构化 催化剂 也有报道。
• Thermodynamic, spectroscopic, and density functional theory studies of allyl aryl and prop-1-enyl aryl ethers. Part 1. Thermodynamic data of isomerization
  作者：Esko Taskinen

  DOI：10.1039/b101837j

  日期：——

  A chemical equilibration study of the relative thermodynamic stabilities of seventy isomeric allyl aryl ethers (a) and (Z)-prop-1-enyl aryl ethers (b) in DMSO solution has been carried out. From the variation of the equilibrium constant with temperature the Gibbs energies, enthalpies, and entropies of isomerization at 298.15 K have been evaluated. Because of their low enthalpies, the (Z)-prop-1-enyl aryl ethers are strongly favored at equilibrium, the Gibbs energies of the a→b isomerization ranging from −12 to −23 kJ mol−1. The entropy contribution is negligible in most reactions, but occasionally small positive values less than +10 J K−1 mol−1 of the entropy of isomerization are found. The equilibration studies were also extended to involve two pairs of related isomeric ethers with a Me substituent on C(2) of the olefinic bond. The Me substituent was found to increase the relative thermodynamic stability of the allylic ethers by ca. 3.4 kJ mol−1.

  通过对70对异构化的烯丙基苯基醚（a）和（Z）-丙-1-烯基苯基醚（b）在DMSO溶液中的化学平衡研究，考察了它们相对热力学稳定性的变化。从平衡常数随温度的变化中，评估了在298.15 K下的异构化吉布斯自由能、焓和熵。由于其低焓值，（Z）-丙-1-烯基苯基醚在平衡状态下具有显著优势，a→b异构化的吉布斯自由能范围从-12至-23 kJ/mol。在大多数反应中，熵的贡献可以忽略不计，但偶尔会发现小于+10 J/K·mol的正值。平衡研究还扩展到涉及两对在烯键C(2)位置带有甲基取代基的相关异构化醚。甲基取代基可以增加烯丙基醚的相对热力学稳定性约3.4 kJ/mol。
• Facile Construction of the Benzofuran and Chromene Ring Systems via Pd^II-Catalyzed Oxidative Cyclization
  作者：So Won Youn、Jeong Im Eom

  DOI：10.1021/ol051264z

  日期：2005.7.1

  text]. We herein report the development of one-pot procedures for the conversion of allyl aryl ethers to 2-methylbenzofurans (via sequential Claisen rearrangement and oxidative cyclization) and for the conversion of aryl homoallyl ethers to chromenes (via direct oxidative cyclization). It is likely that both reactions proceed via a common Pd-catalyzed pathway involving olefin activation, nucleophilic

  [反应：请参见文字]。我们在本文中报道了一锅法的发展，该方法用于将烯丙基芳基醚转化为2-甲基苯并呋喃（通过顺序的克莱森重排和氧化环化）和用于将芳基高烯丙基醚转化为苯甲基（通过直接氧化环化）。这两种反应都有可能通过常见的Pd催化途径进行，涉及烯烃活化，亲核攻击和β-氢化物消除。
• Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
  作者：Jingyang Wang、Yu Wang、Guangni Ding、Xiaoyu Wu、Liqun Yang、Sijie Fan、Zhaoguo Zhang、Xiaomin Xie

  DOI：10.1016/j.tetlet.2021.153341

  日期：2021.9

  An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD) as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of

  以市售Ni(COD)为催化剂前驱体、简单取代联吡啶为配体和空气稳定的氢硅烷，开发了一种高效、温和的芳基烯丙基醚催化脱烯丙基化方法。该工艺与多种官能团兼容，并且能够以优异的产率和选择性获得所需的苯酚产品。此外，通过检测或分离关键中间体，机制研究证实脱烯丙基化经历了-烯丙基镍中间体途径。