4-Dodecyl-6-(3-hydroxy-propyl)-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester | 150252-79-2

• 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: 4-Dodecyl-6-(3-hydroxy-propyl)-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester
• CAS: 150252-79-2
• 化学式: C₂₈H₄₄N₂O₄
• 分子量: 472.668
• InChiKey: HJESIKISYZYTAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  579.6±60.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  34.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-Dodecyl-6-(3-hydroxy-propyl)-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester 在 palladium on activated charcoal 、 三乙胺 氢气 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 生成 (5α,9β,10β)-7-amino-9-dodecyl-1-oxa-6,8-diazaspiro<4.5>dec-7-ene-10-carboxylic acid hydrochloride
  参考文献：
  名称：

  Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision of the structure of crambines B and C1

  摘要：

  Crambines A (7) (eight steps, 22%), B (45d) (eight Steps, 19%), C1 (9d) (seven steps, 21%), and C2 (9a) (seven steps, 27%) have been synthesized expediently and stereospecifically by a biomimetic route from methyl acetoacetate. Aminodihydropyrimidines 39 and 40 are formed efficiently from enone ester 36 by a two-step procedure involving addition of O-methylisourea to give methoxydihydropyrimidine 37 followed by displacement of the methoxy group of 37 with ammonia. Hydrogenolysis of 40a and 40d afford crambines C2 and C1, respectively. Mesylation of the alcohol of 39a or 40a followed by Et3N-catalyzed cyclization and hydrogenolysis affords crambine A (7). Aminal formation from 39d or 40d in CHCl3 followed by hydrogenolysis proceeds stereospecifically to provide crambine B (45d). The structure of crambine B has been revised to the stereochemistry shown in 45 and both crambines B and Cl have a seven rather than five-carbon guanidino alkyl chain.

  DOI：

  10.1021/jo00067a014
• 作为产物：
  描述：

  6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-dodecyl-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester 生成 4-Dodecyl-6-(3-hydroxy-propyl)-2-methoxy-1,4-dihydro-pyrimidine-5-carboxylic acid benzyl ester 、 (5S,9S,10R)-9-Dodecyl-7-imino-1-oxa-6,8-diaza-spiro[4.5]decane-10-carboxylic acid benzyl ester; hydrochloride 、 (5R,9R,10R)-9-Dodecyl-7-imino-1-oxa-6,8-diaza-spiro[4.5]decane-10-carboxylic acid benzyl ester; hydrochloride 、 (5R,9S,10R)-9-Dodecyl-7-imino-1-oxa-6,8-diaza-spiro[4.5]decane-10-carboxylic acid benzyl ester; hydrochloride
  参考文献：
  名称：

  Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision of the structure of crambines B and C1

  摘要：

  Crambines A (7) (eight steps, 22%), B (45d) (eight Steps, 19%), C1 (9d) (seven steps, 21%), and C2 (9a) (seven steps, 27%) have been synthesized expediently and stereospecifically by a biomimetic route from methyl acetoacetate. Aminodihydropyrimidines 39 and 40 are formed efficiently from enone ester 36 by a two-step procedure involving addition of O-methylisourea to give methoxydihydropyrimidine 37 followed by displacement of the methoxy group of 37 with ammonia. Hydrogenolysis of 40a and 40d afford crambines C2 and C1, respectively. Mesylation of the alcohol of 39a or 40a followed by Et3N-catalyzed cyclization and hydrogenolysis affords crambine A (7). Aminal formation from 39d or 40d in CHCl3 followed by hydrogenolysis proceeds stereospecifically to provide crambine B (45d). The structure of crambine B has been revised to the stereochemistry shown in 45 and both crambines B and Cl have a seven rather than five-carbon guanidino alkyl chain.

  DOI：

  10.1021/jo00067a014