5-methoxy 4-methyl benzo[d][1,3]dioxole | 607351-59-7

• 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: 5-methoxy 4-methyl benzo[d][1,3]dioxole
• 英文别名: 5-methoxy-4-methylbenzo[1,3]dioxole；1,3-Benzodioxole, 5-methoxy-4-methyl-；5-methoxy-4-methyl-1,3-benzodioxole
• CAS: 607351-59-7
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: VHHKIWGXWLYTDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  5-methoxy 4-methyl benzo[d][1,3]dioxole 在 三氯氧磷 作用下， 以 苯 为溶剂， 反应 24.25h， 生成 ethyl 3-(6-methoxy 7-methyl benzo[d][1,3]dioxol-5-yl)-(E)-2-propionate
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056
• 作为产物：
  描述：

  3,4-Methylendioxy-phenyl-formiat 在 盐酸 、 氢氧化钾 、 正丁基锂 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 17.17h， 生成 5-methoxy 4-methyl benzo[d][1,3]dioxole
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056

文献信息

• Synthesis of (±)-phthalascidin 622
  作者：R. Razafindrabe Christian、Aubry Sylvain、Bourdon Benjamin、Andriantsiferana Marta、Pellet-Rostaing Stephane、Lemaire Marc

  DOI：10.1007/s11426-010-4075-z

  日期：2010.9

  synthesis of functionalized phenolic α-amino-alcohols (±)-8 and (±)-16 as synthetic precursors of the catechol tetrahydroisoquinoline structure of phthalascidin 650 was disclosed. (±)-8 was prepared in 5 steps from the commercially available sesamol. Starting from 3-methyl catechol 5, 8 steps gave rise to the synthesis of phenolic α-amino-alcohol (±)-16 in 27% overall yield. This synthetic strategy involved

  公开了作为邻苯二酚650的邻苯二酚四氢异喹啉结构的合成前体的官能化酚类α-氨基醇（±）-8和（±）-16的合成。（±） - 8是在5个步骤制备由市售芝麻酚。从3-甲基邻苯二酚5开始，经过8个步骤，以27％的总收率合成了酚类α-氨基醇（±）-16。该合成策略涉及对完全官能化的芳族醛13进行精细加工，并将其转化为酚类α-氨基醇（±）-16通过Knoevenagel缩合反应，同时还原硝基烯酮和酯官能团，以及苄基保护基的氢解。在另外4个步骤后获得了五环（±）-4。在酚类α-氨基醇（±）-16和N-保护的α-氨基醛4之间进行Pictet-Spengler环化反应，可以得到（1,3'）- N-甲基化和N-化的双-四氢异喹啉17 Fmoc已删除。最后一步是Swern氧化，可实现预期的分子内缩合。
• Synthetic studies towards (±)-phthalascidin 650: synthesis of a fully functionalized N-protected-α-amino-aldehyde
  作者：Sylvain Aubry、Christian R. Razafindrabe、Benjamin Bourdon、Stéphane Pellet-Rostaing、Marc Lemaire

  DOI：10.1016/j.tetlet.2007.10.111

  日期：2007.12

  An efficient synthesis of fully functionalized N-protected alpha-amino-aldehyde (+/-)-13 as synthetic precursor of the tetra-hydroisoquinoline alkaloid phthalascidin 650 is reported. Starting from sesamol 6, 11 steps are required to give rise to the desired N-protected alpha-amino-aldehyde (+/-)-13 in 25% overall yield. This synthetic strategy involves the elaboration of fully functionalized aromatic aldehyde 7 and its transformation into an alpha-amino-alcohol through a Knoevenagel condensation. The phthalimidomethyl derivative (+/-)-11 was then synthesised from 8 by a Bischler-Napieralski reaction, a diastereoselective hydrogenation of the resultant dihydroisoquinoline and transformed into the corresponding N-protected alpha-amino-aldehyde (+/-)-13. (C) 2007 Elsevier Ltd. All rights reserved.
• Development of Novel Antioxidants:  Design, Synthesis, and Reactivity
  作者：Helmi H. Hussain、Gordana Babic、Tony Durst、James S. Wright、Mihaela Flueraru、Alexandru Chichirau、Leonid L. Chepelev

  DOI：10.1021/jo0301090

  日期：2003.9.1

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.
• Stabilized polyolefin compositions
  申请人：Kumar Vijayendra

  公开号：US20070149660A1

  公开（公告）日：2007-06-28

  Disclosed are compositions comprising antioxidants and stabilizers, such as, acid scavengers or organic phosphorus stabilizers, and optionally further comprising co-stabilizers. The disclosed compositions are useful as stabilizers for polyolefins and other polymeric materials. The disclosed compositions and methods generally provide longer shelf lifes and better oxidative resistance to materials than currently available antioxidants.
• Lubricant oil compositions
  申请人：Cholli L. Ashok

  公开号：US20070161522A1

  公开（公告）日：2007-07-12

  Compositions comprise first antioxidants and first additives, such as, a surface additives, performance enhancing additives and lubricant protective additives and optionally second additives and/or second antioxidants. The compositions are useful to improve lubricants, lubricant oils and other lubricant materials. The compositions and methods generally provide longer shelf lives, increased oxidative resistance, improved quality and/or enhanced performance to lubricants or lubricant oils.