3-(3-benzyloxyphenoxy)propionaldehyde dimethyl acetal | 144852-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-benzyloxyphenoxy)propionaldehyde dimethyl acetal
• 英文别名: 1-(3,3-Dimethoxypropoxy)-3-phenylmethoxybenzene
• CAS: 144852-07-3
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: UZSWPWAUUCHGCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-benzyloxyphenoxy)propionaldehyde dimethyl acetal 在 正丁基锂 、 对甲苯磺酸 、 mercury dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1-(4-(苄氧基)-2-羟基苯基)-2-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  4-Chromenesulphones: synthesis and transformation to isoflavonoid models

  摘要：

  Novel sulphones derived from chromenes through Substitution at C-4 were prepared. It has been shown that, after conjugate addition of phenyl lithium and sulphone function manipulation on the adducts, these molecules lead to isoflavan, isoflavene and isoflavanone models. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01653-2
• 作为产物：
  描述：

  3-苄氧基苯甲醛 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 3-(3-benzyloxyphenoxy)propionaldehyde dimethyl acetal
  参考文献：
  名称：

  Structure–activity relationship of wedelolactone analogues: Structural requirements for inhibition of Na+,K+-ATPase and binding to the central benzodiazepine receptor

  摘要：

  Coumestans 2a-i, bearing different patterns of substitution in A- and D-rings, were synthesized and evaluated as inhibitors of kidney Na+, K+ -ATPase and ligands for the central benzodiazepine (BZP) receptor. The presence of a hydroxyl group in position 2 favours the effect on Na+, K+ -ATPase but decreases the affinity for the BZP receptor, allowing the design of more selective molecules than the natural wedelolactone. On the other hand, the presence of a catechol in ring D is important for the effect on both molecular targets.

  DOI：

  10.1016/j.bmc.2006.07.053

文献信息

• A Convenient Synthesis of (±)-4-Prenylpterocarpin
  作者：Antonio L. Coelho、Mario L. A. A. Vasconcellos、Alessandro B. C. Simas、Jaime A. Rabi、Paulo R. R. Costa

  DOI：10.1055/s-1992-26257

  日期：——

  Coupling of 7-methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran (4a) with 2-chloromercurio-4,5-methylenedioxyphenol (5) yields (±)-6a, 12a-cis-dihydro-3-methoxy-4-(3-methyl-2-butenyl)-6H-[1,3]dioxolo [5,6]benzofuro[3,2-c][1]benzopyran (6; ±-4-prenylpterocarpin) in an efficient manner. An improved procedure for the preparation of chromenes is reported.

  7-甲氧基-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃（4a）与2-氯汞-4,5-亚甲基二氧基苯酚（5）的偶联以有效的方式产生（±）-6a，12a-顺式二氢-3-甲氧基-4-(3-甲基-2-丁烯基)-6H-[1,3]二氧杂环戊烯并[5,6]苯并呋喃并[3,2-c][1]苯并吡喃（6；±-4-异戊烯基蝶呤）。本文报道了一种改进的苯并吡喃制备方法。
• Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation
  作者：Alcides J.M da Silva、Paulo A Melo、Noelson M.V Silva、Flávia V Brito、Camilla D Buarque、Daniele V de Souza、Verônica P Rodrigues、Elisa S.C Poças、François Noël、Edson X Albuquerque、Paulo R.R Costa

  DOI：10.1016/s0960-894x(00)00621-1

  日期：2001.2

  Five coumestans with different patterns of oxygenation in rings A and D were synthesized from resorcinol and aromatic aldehydes, and screened for their antimyotoxic activity. The most potent compound (2b, IC50= 1 muM) was selected for study of its pharmacological profile. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Structure–activity relationship of wedelolactone analogues: Structural requirements for inhibition of Na+,K+-ATPase and binding to the central benzodiazepine receptor
  作者：Elisa S.C. Pôças、Daniele V.S. Lopes、Alcides J.M. da Silva、Paulo H.C. Pimenta、Fernanda B. Leitão、Chaquip D. Netto、Camilla D. Buarque、Flávia V. Brito、Paulo R.R. Costa、François Noël

  DOI：10.1016/j.bmc.2006.07.053

  日期：2006.12

  Coumestans 2a-i, bearing different patterns of substitution in A- and D-rings, were synthesized and evaluated as inhibitors of kidney Na+, K+ -ATPase and ligands for the central benzodiazepine (BZP) receptor. The presence of a hydroxyl group in position 2 favours the effect on Na+, K+ -ATPase but decreases the affinity for the BZP receptor, allowing the design of more selective molecules than the natural wedelolactone. On the other hand, the presence of a catechol in ring D is important for the effect on both molecular targets.
• 4-Chromenesulphones: synthesis and transformation to isoflavonoid models
  作者：Alessandro Bolis C. Simas、Luis F.O. Furtado、Paulo R.R. Costa

  DOI：10.1016/s0040-4039(02)01653-2

  日期：2002.9

  Novel sulphones derived from chromenes through Substitution at C-4 were prepared. It has been shown that, after conjugate addition of phenyl lithium and sulphone function manipulation on the adducts, these molecules lead to isoflavan, isoflavene and isoflavanone models. (C) 2002 Elsevier Science Ltd. All rights reserved.