2-formyl-5-pentylresorcinol 1,3-bis-(methoxymethyl) ether | 137059-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-formyl-5-pentylresorcinol 1,3-bis-(methoxymethyl) ether
• 英文别名: 2,6-bis(methoxymethoxy)-4-pentylbenzaldehyde
• CAS: 137059-80-4
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: DATROHWGLDMAST-UHFFFAOYSA-N

物化性质

• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-formyl-5-pentylresorcinol 1,3-bis-(methoxymethyl) ether 在 盐酸 、 sodium hydride 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 3-(2-Bromo-ethyl)-5-hydroxy-7-pentyl-chromen-2-one
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032
• 作为产物：
  描述：

  3,5-二羟基戊苯 在 正丁基锂 、 sodium hydride 作用下， 反应 6.0h， 生成 2-formyl-5-pentylresorcinol 1,3-bis-(methoxymethyl) ether
  参考文献：
  名称：

  3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes

  摘要：

  The reaction of alpha-(diethylphosphono)-gamma-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

  DOI：

  10.1021/jo00027a032

文献信息

• High-Pressure Diels−Alder Cycloadditions between Benzylideneacetones and 1,3-Butadienes: Application to the Synthesis of (<i>R,R</i>)-(−)- and (<i>S,S</i>)-(+)-Δ⁸-Tetrahydrocannabinol
  作者：Eleonora Ballerini、Lucio Minuti、Oriana Piermatti

  DOI：10.1021/jo100785w

  日期：2010.6.18

  combination with the mild Lewis acid HfCl4·2THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloadducts, that are useful precursors for the expeditious construction of the privileged 6,6-dimethyltetrahydro-6H-benzo[c]chromene skeleton. Application to the synthesis of Δ8-trans-THC in both enantiomeric pure forms is based on the successful

  据报道，各种烷氧基/烷基取代的亚苄基丙酮与甲基-1,3-丁二烯的高压Diels-Alder反应。高压（8-11 kbar）与温和的路易斯酸HfCl 4 ·2THF结合活化使这些反应有效和区域选择性地产生了一系列邻位取代的环己烯基-苯环加合物，它们对于快速构建环己烯基有用的前体。特权的6,6-二甲基四氢-6 H-苯并[ c ]亚甲基骨架。到Δ的合成应用8 -反式-THC在两种对映体纯的形式是基于由SAMP -腙的方法选择环加成的成功解决。
• Experimental and Computational Studies into an ATPH-Promoted exo-Selective IMDA Reaction: A Short Total Synthesis of Δ9-THC
  作者：Emma L. Pearson、Nicholas Kanizaj、Anthony C. Willis、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1002/chem.201001176

  日期：——

  of fortune: The inherent cis stereoselectivity of an intramolecular Diels–Alder reaction is reversed through promotion with aluminum tris(2,6‐diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ9‐tetrahydrocannabinol (see scheme). Computational studies predict the experimental findings and shed light on the stereocontrolling influences at play in these Diels–Alder reactions

  幸运的逆转：固有顺式分子内Diels-Alder反应的立体选择性是通过促进与铝，三（2,6- diphenylphenoxide）（ATPH）反转，使天然产物Δ的总合成9 -四氢大麻酚（参见方案）。计算研究预测了实验结果，并阐明了这些Diels-Alder反应中立体控制的影响。
• High Pressure Diels−Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ⁶-<i>Cis</i>-Cannabidiol
  作者：Eleonora Ballerini、Lucio Minuti、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1021/jo9005365

  日期：2009.6.5

  Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a-cyano-mesyl-tetrahydro-6H-benzo[c]chromen-6-ones in moderate to excellent yield. The synthesis of cis-1-hydroxy-9-methyl-3-pentyl-6a,7, 10,10a-tetrahydro-benzo[c]chromen-6-one as precursor of Delta(6)-3,4-cis-cannabidiol (Delta(6)-cis-CBD) and Delta(8)-cis-tetrahydrocannabinol (Delta(8)-cis-THC) is outlined.