2-formyl-5-pentylresorcinol 3-methoxymethyl ether | 137059-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formyl-5-pentylresorcinol 3-methoxymethyl ether
• 英文别名: 2-hydroxy-6-(methoxymethoxy)-4-pentylbenzaldehyde
• CAS: 137059-81-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: WVPDVBDQLYCOBO-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±42.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formyl-5-pentylresorcinol 3-methoxymethyl ether 在 sodium hydride 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙腈 为溶剂， 反应 7.0h， 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 盐酸 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2-formyl-5-pentylresorcinol 3-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

• 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。
• 3-Vinylcoumarins and 3-vinylchromenes as dienes. Application to the synthesis of 3,4-fused coumarins and chromenes
  作者：Toru Minami、Yasuyuki Matsumoto、Seigo Nakamura、Shinichiro Koyanagi、Masahiko Yamaguchi

  DOI：10.1021/jo00027a032

  日期：1992.1

  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.