(R)-1,1-bis(4-(allyloxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol | 1355235-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1,1-bis(4-(allyloxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol
• 英文别名: (2R)-1,1-bis(3,5-dimethoxy-4-prop-2-enoxyphenyl)-2-methylpent-4-en-1-ol
• CAS: 1355235-10-7
• 化学式: C₂₈H₃₆O₇
• 分子量: 484.59
• InChiKey: NEHFAIDYHVDGIO-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-1,1-bis(4-(allyloxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol 在 咪唑 、 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 正丁基锂 、 1,3-二甲基巴比妥酸 、 palladium diacetate 、 三苯基膦 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 rac-(3S,4S)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Total Synthesis of (−)-Sacidumlignans B and D

  摘要：

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.

  DOI：

  10.1021/jo2021696
• 作为产物：
  描述：

  2-(allyloxy)-5-bromo-1,3-dimethoxybenzene 、 (R)-2-Methyl-4-pentenoic acid phenylmethyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以63%的产率得到(R)-1,1-bis(4-(allyloxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol
  参考文献：
  名称：

  Total Synthesis of (−)-Sacidumlignans B and D

  摘要：

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.

  DOI：

  10.1021/jo2021696

文献信息

• Total Synthesis of (−)-Sacidumlignans B and D
  作者：Jeetendra Kumar Rout、C. V. Ramana

  DOI：10.1021/jo2021696

  日期：2012.2.3

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.