2-Methoxymethoxy-5-methoxytoluene | 127136-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methoxymethoxy-5-methoxytoluene
• 英文别名: 4-Methoxy-1-(methoxymethoxy)-2-methylbenzene
• CAS: 127136-79-2
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: BUKGLKJBILZLLU-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C(Press: 0.3 Torr)
• 密度：
  1.031±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-Methoxymethoxy-5-methoxytoluene 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-2-(4-methoxy-2-methylphenoxy)thiazole
  参考文献：
  名称：

  Phenoxy thiazole derivatives as potent and selective acetyl-CoA carboxylase 2 inhibitors: Modulation of isozyme selectivity by incorporation of phenyl ring substituents

  摘要：

  A phenyl ring substitution strategy was employed to optimize the ACC2 potency and selectivity profiles of a recently discovered phenoxy thiazolyl series of acetyl-CoA carboxylase inhibitors. Ring substituents were shown to dramatically affect isozyme selectivity. Modifications that generally impart high levels of ACC2 selectivity (> 3000-fold) while maintaining excellent ACC2 potency (IC(50)s similar to 9-20 nM) were identified. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.022
• 作为产物：
  描述：

  4-甲氧基苯酚 在 正丁基锂 、 溴 、 sodium hydride 作用下， 以 乙醚 、 正己烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-Methoxymethoxy-5-methoxytoluene
  参考文献：
  名称：

  Phenoxy thiazole derivatives as potent and selective acetyl-CoA carboxylase 2 inhibitors: Modulation of isozyme selectivity by incorporation of phenyl ring substituents

  摘要：

  A phenyl ring substitution strategy was employed to optimize the ACC2 potency and selectivity profiles of a recently discovered phenoxy thiazolyl series of acetyl-CoA carboxylase inhibitors. Ring substituents were shown to dramatically affect isozyme selectivity. Modifications that generally impart high levels of ACC2 selectivity (> 3000-fold) while maintaining excellent ACC2 potency (IC(50)s similar to 9-20 nM) were identified. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.022

文献信息

• The directed ortho-lithiation of aryl tetramethylphosphorodiamidates.
  作者：Mitsuaki WATANABE、Mutsuhiro DATE、Kenji KAWANISHI、Takako HORI、Sunao FURUKAWA

  DOI：10.1248/cpb.38.2637

  日期：——

  Aryl tetramethylphosphorodiamidates were effectively ortho-lithiated with sec-BuLi in tetrahydrofuran at -105°C.The resulting lithiated species were trapped with a variety of electrophiles at -105°C to provide ortho-substituted phosphorodiamidates. When the lithiation was carried out at -78°C, O→C migration of the bis(dimethylamino)phosphoryl group took place rapidly and 2-hydroxyarylphosphonic tetramethyldiamides were produced regioselectively. The ortho-directing ability of the phosphorodiamidates was investigated by intermolecular competition experiments with other directed metalation groups.

  芳基四甲基膦双胺盐在四氢呋喃中，以-105°C温度下通过第二丁基锂有效实现邻位锂化。所得锂化物种与各种亲电试剂在-105°C温度下反应，生成邻位取代的膦双胺盐。当锂化反应在-78°C进行时，双（二甲基氨基）膦基团迅速发生O→C迁移，选择性地生成2-羟基芳基膦酸四甲基双胺盐。通过与其他导向金属化基团的分子间竞争实验研究了膦双胺盐的邻位导向能力。
• Quantitative Structure–Activity Analyses of Novel Hydroxyphenylurea Derivatives as Antioxidants
  作者：Kazuya Nakao、Ryo Shimizu、Hitoshi Kubota、Mikiko Yasuhara、Yoshimasa Hashimura、Toshikazu Suzuki、Toshio Fujita、Hiroshi Ohmizu

  DOI：10.1016/s0968-0896(98)00039-x

  日期：1998.6

  importance in governing the inhibitory potency. An increase in the electron donating property of substituents toward the phenolic hydroxyl group enhanced the antioxidative activity by the stabilization of an electron-deficient radical-type transition state. The steric shielding by ortho-substituents stabilized the phenoxy radicals formed following the transition state. Derivatives having the carboxyl group

  合成了一系列取代的羟基苯基脲，其化学结构是基于天然抗氧化剂，维生素E（α-生育酚）和尿酸的结构设计的。它们显示出对脂质过氧化的高抑制活性。为了深入了解抑制反应的机理，我们定量分析了它们的构效关系。取代基对酚羟基的电子和空间效应显示出对控制抑制效力的重要性。取代基对酚羟基的给电子性的增加通过稳定电子缺陷的自由基型过渡态而增强了抗氧化活性。邻位取代基的空间屏蔽作用稳定了过渡态后形成的苯氧基。推测具有羧基的衍生物仅是弱活性的，这是因为酚羟基与羧酸根阴离子的分子间离子-偶极相互作用会延迟过渡态的形成。
• WATANABE, MITSUAKI;DATE, MUTSUHIRO;KAWANISHI, KENJI;HORI, TAKAKO;FURUKAWA+, CHEM. AND PHARM. BULL., 38,(1990) N0, C. 2637-2643
  作者：WATANABE, MITSUAKI、DATE, MUTSUHIRO、KAWANISHI, KENJI、HORI, TAKAKO、FURUKAWA+

  DOI：——

  日期：——
• Phenoxy thiazole derivatives as potent and selective acetyl-CoA carboxylase 2 inhibitors: Modulation of isozyme selectivity by incorporation of phenyl ring substituents
  作者：Richard F. Clark、Tianyuan Zhang、Xiaojun Wang、Rongqi Wang、Xiaolin Zhang、Heidi S. Camp、Bruce A. Beutel、Hing L. Sham、Yu Gui Gu

  DOI：10.1016/j.bmcl.2007.01.022

  日期：2007.4

  A phenyl ring substitution strategy was employed to optimize the ACC2 potency and selectivity profiles of a recently discovered phenoxy thiazolyl series of acetyl-CoA carboxylase inhibitors. Ring substituents were shown to dramatically affect isozyme selectivity. Modifications that generally impart high levels of ACC2 selectivity (> 3000-fold) while maintaining excellent ACC2 potency (IC(50)s similar to 9-20 nM) were identified. (c) 2007 Elsevier Ltd. All rights reserved.