4-甲氧基酞烷 | 1028202-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 4-甲氧基酞烷
• 英文名称: 4-methoxyphthalan
• 英文别名: 1,3-Dihydro-4-methoxyisobenzofuran；4-methoxy-1,3-dihydro-2-benzofuran
• CAS: 1028202-56-3
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: ZNMNOKHVTAGASD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基酞烷 在 4,4'-二叔丁基苯并 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以80%的产率得到(2-methoxy-6-methylphenyl)methanol
  参考文献：
  名称：

  Regioselective reductive opening of substituted phthalans: synthetic applications

  摘要：

  The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.072
• 作为产物：
  描述：

  [2-(羟甲基)-3-甲氧基苯基]甲醇 在 三乙基硅烷 、 manganese(IV) oxide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以86%的产率得到4-甲氧基酞烷
  参考文献：
  名称：

  A one-pot tandem oxidation–reduction protocol for the synthesis of cyclic ethers from their diols

  摘要：

  A novel and an efficient one-pot cyclization method for the preparation of cyclic ethers from their diols via a tandem oxidation-reduction protocol using a cocktail of MnO2/Et3SiH/CF3COOH is reported. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.046

文献信息

• Visible light mediated oxidation of benzylic sp³ C–H bonds using catalytic 1,4-hydroquinone, or its biorenewable glucoside, arbutin, as a pre-oxidant
  作者：Laura C. Finney、Lorna J. Mitchell、Christopher J. Moody

  DOI：10.1039/c7gc03741d

  日期：——

  a sustainable alternative for the late stage oxidative functionalization of benzylic C–H bonds. It is applicable to a range of cyclic benzylic ethers such as isochromans and phthalans, and simple benzyl alkyl ethers. It can also be applied in the oxidation of benzylic amines into amides, and of diarylmethanes into the corresponding ketones. Mechanistic studies suggest that the reaction proceeds by

  苯甲醚经过可见光诱导的C–H活化和氧的插入，以中等至良好的产率得到相应的苯甲酸酯。该条件采用亚化学计量的1，4-氢醌与氯化铜（II）二水合物作为电子转移介体，氧气作为末端氧化剂，碳酸二甲酯作为溶剂在可见光照射下。天然存在的糖苷，熊果苷，可商购获得，或可通过提取熊果（Arctostaphylos uva-ursi）或象耳（Bergenia crassifolia）的叶子获得）可以用作1,4-对苯二酚的生物可再生来源。该方法利用了可见光照射后醌氧化能力的提高，并为苄基CH键的后期氧化官能化提供了一种可持续的替代方法。它适用于各种环状苄基醚，例如异色满和酞菁，以及简单的苄基烷基醚。它也可用于将苄基胺氧化为酰胺，并将二芳基甲烷氧化为相应的酮。机理研究表明，该反应通过光激发的三重态苯并醌进行H吸收来进行，从而产生一个苄基，该苄基随后与分子氧反应。
• Iridium(<scp>iii</scp>)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate
  作者：N. Mace Weldy、A. G. Schafer、C. P. Owens、C. J. Herting、A. Varela-Alvarez、S. Chen、Z. Niemeyer、D. G. Musaev、M. S. Sigman、H. M. L. Davies、S. B. Blakey

  DOI：10.1039/c6sc00190d

  日期：——

  the interplay of experimental and computational insights. The reaction is tolerant of a variety of diazoacetate precursors and is found to be heavily influenced by the steric and electronic properties of the substrate. Phthalan and dihydrofuran derivatives are functionalized in good yields and excellent enantioselectivities.

  据报道，使用基于实验和计算见解的相互作用而开发的新型 Ir( III )-双(咪唑啉基)苯基催化剂家族，仅接受受体的金属碳烯进行分子间对映选择性 C-H 官能化。该反应能够耐受多种重氮乙酸盐前体，并且发现该反应很大程度上受到底物的空间和电子性质的影响。苯并呋喃和二氢呋喃衍生物以良好的收率和优异的对映选择性进行官能化。
• Regioselective reductive opening of substituted phthalans: synthetic applications
  作者：Daniel García、Francisco Foubelo、Miguel Yus

  DOI：10.1016/j.tet.2008.02.072

  日期：2008.5

  The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations. (c) 2008 Elsevier Ltd. All rights reserved.
• A one-pot tandem oxidation–reduction protocol for the synthesis of cyclic ethers from their diols
  作者：Biswajit Panda、Tarun K. Sarkar

  DOI：10.1016/j.tetlet.2008.09.046

  日期：2008.11

  A novel and an efficient one-pot cyclization method for the preparation of cyclic ethers from their diols via a tandem oxidation-reduction protocol using a cocktail of MnO2/Et3SiH/CF3COOH is reported. (c) 2008 Elsevier Ltd. All rights reserved.