1-(氯甲基)-3,5-二(甲氧基甲氧基)苯 | 574742-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(氯甲基)-3,5-二(甲氧基甲氧基)苯
• 英文名称: 3,5-bis-methoxymethoxybenzyl chloride
• 英文别名: 1-(Chloromethyl)-3,5-bis(methoxymethoxy)benzene；1-(chloromethyl)-3,5-bis(methoxymethoxy)benzene
• CAS: 574742-56-6
• 化学式: C₁₁H₁₅ClO₄
• 分子量: 246.691
• InChiKey: IKMIJJCVNBIZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1-(氯甲基)-3,5-二(甲氧基甲氧基)苯 在 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3S)-6-[(E)-2-[3,5-bis(methoxymethoxy)phenyl]ethenyl]-3-[3,5-dimethoxy-4-(methoxymethoxy)phenyl]-2-(methoxymethoxymethyl)-2,3-dihydro-1,4-benzodioxine
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035
• 作为产物：
  描述：

  methyl 3,5-bis(methoxymethoxy)benzoate 在 lithium aluminium tetrahydride 、 TEA 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(氯甲基)-3,5-二(甲氧基甲氧基)苯
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035

文献信息

• Total Synthesis of (±)-Aiphanol, a Novel Cyclooxygenase-inhibitory Stilbenolignan
  作者：Atsuhito Kuboki、Toru Yamamoto、Susumu Ohira

  DOI：10.1246/cl.2003.420

  日期：2003.5

  (±)-Aiphanol has been stereoselectively synthesized through IBX-mediated o-quinone formation, and through [4+2] cycloaddition of the o-quinone and cinnamyl alcohol unit.

  通过 IBX 介导的邻醌形成和邻醌与肉桂醇单元的 [4+2] 环加成，立体选择性地合成了 (±)-Aiphanol 。
• [EN] SCHWEINFURTHIN ANALOGUES<br/>[FR] ANALOGUES DE SCHWEINFURTHINES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2005092878A3

  公开（公告）日：2006-05-04