1,2-dibenzyloxy-4-methoxybenzene | 88755-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-dibenzyloxy-4-methoxybenzene
• 英文别名: 3,4-Bis-benzyloxy-anisol；Benzene, 4-methoxy-1,2-bis(phenylmethoxy)-；4-methoxy-1,2-bis(phenylmethoxy)benzene
• CAS: 88755-15-1
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: LRYSAWNMQJUJNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1,2-dibenzyloxy-4-methoxybenzene 在 palladium on activated charcoal 氢气 、 1,1-二苯基-2-苦味酰肼 作用下， 以 氘代甲醇 、 丙酮 为溶剂， 反应 0.17h， 生成 4-甲氧基-1,2-苯醌
  参考文献：
  名称：

  Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents

  摘要：

  The DPPH (2,2-diphenyl-l-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, Since they affect the susceptibility toward nucleophilic attacks on o-quinone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.040
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 氢氧化钾 、 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 1,2-dibenzyloxy-4-methoxybenzene
  参考文献：
  名称：

  Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo(c)phenanthridine alkaloids. 1. Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides.

  摘要：

  为了建立一种通用的苯并[c]菲啶生物碱合成方法，对Robinson合成方法进行了改进。通过将两个乙酰苯衍生物（15和16）与十一种苯甲醛衍生物（19a-k）缩合，制备了十三种查尔酮（7a-m）作为基本起始材料。除了一个查尔酮（7m）外，这些查尔酮（7a-l）的氰化反应得到了相应的2,4-双芳基-4-氧代丁腈（8a-l）。还制备了十一种2,4-双芳基-4-氧代丁酰胺（9a-k）。

  DOI：

  10.1248/cpb.31.3024

文献信息

• Stereoselective Syntheses of (-)-Podorhizol Lignan and its Derivatives:<i>erythro</i>and<i>threo</i>Preferential Aldol Condensation of Potassium Enolate from γ-Butyrolactone with Alkoxybenzaldehyde
  作者：Satoshi YAMAUCHI、Mitsuo MACHI、Yoshiro KINOSHITA

  DOI：10.1271/bbb.63.1453

  日期：1999.1

  (-)-Podorhizol (1) was stereoselectively synthesized by erythro preferential aldol condensation of 3,4,5-trimethoxy- benzaldehyde with potassium enolate from (+)-(R)-3- (3,4-methylenedioxybenzyl)-4-butanolide (2) (erythro:threo=85:15). Erythro selectivity was observed in the aldol condensation of many alkoxybenzaldehydes with potassium enolate from (+)-γ-butyrolactone 2. However, benzaldehydes having methoxy groups at both the 2 and 6 positions gave threo selectivity in the aldol condensation with potassium enolate from (+)-γ-butyrolactone 2.

  (-)-Podorhizol (1) 是通过 3,4,5-三甲氧基苯甲醛与来自 (+)-(R)-3-(3,4-二氧基苯甲基)-4-丁内酯 (2) 的钾烯醇进行红脆优先的醇缩合反应立体选择性合成的（红脆:反式=85:15）。在许多烷氧基苯甲醛与来自 (+)-γ-丁内酯 2 的钾烯醇的醇缩合反应中观察到了红脆选择性。然而，具有在 2 和 6 位均为甲氧基取代基的苯甲醛在与来自 (+)-γ-丁内酯 2 的钾烯醇的醇缩合反应中则表现出反式选择性。
• Aihara, Kazuhiro; Urano, Yasuteru; Higuchi, Tsunehiko, Journal of the Chemical Society. Perkin transactions II, 1993, # 11, p. 2165 - 2170
  作者：Aihara, Kazuhiro、Urano, Yasuteru、Higuchi, Tsunehiko、Hirobe, Masaaki

  DOI：——

  日期：——
• Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4020(98)00235-x

  日期：1998.5

  Two efficient enantiospecific syntheses of wiedendiol-A (1) from (-)-sclareol (7), via 11-bromo-8-drimene (11) and 8-drimen-11-al (3), are reported. The first enantiospecific synthesis of wiedendiol-B (2), via 8S,9S-driman-11-al (26), by two alternative routes starting from 7 and (+)-cis-abienol (8) is also described. 21 prepared from protocatechualdehyde (17) was used as aromatic synthon for preparing 1 and 2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Funke,A. et al., Bulletin de la Societe Chimique de France, 1960, p. 1644 - 1646
  作者：Funke,A. et al.

  DOI：——

  日期：——
• Enantiospecific Synthesis of Wiedendiol-B from (−)-Sclareol and (+)-cis-Abienol
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、Rachid Chahboun

  DOI：10.1016/s0040-4039(97)10119-8

  日期：1997.11

  The first enantiospecific synthesis of the cholesteryl ester transfer protein (CETP) inhibitor wiedendiol-B (1) is described. The drimanic synthon was prepared from (-)-sclareol (4) and (+)-cis-abienol (13) by two alternative routes. The key steps of the reaction sequences are the chemo-and diastereoselective hydrogenation of the C-8-C-9 double bond of enal 6 and the stereoselective cationic hydrogenation of the hydroxyl group of 13, respectively, and the selective reduction of benzyl groups of 15. (C) 1997 Elsevier Science Ltd.