4-((1S,2R,10aS)-1-Formyl-7-methoxy-1-methyl-1,2,3,9,10,10a-hexahydro-phenanthren-2-yl)-butyric acid methyl ester | 796850-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4-((1S,2R,10aS)-1-Formyl-7-methoxy-1-methyl-1,2,3,9,10,10a-hexahydro-phenanthren-2-yl)-butyric acid methyl ester
• 英文别名: methyl 4-[(1S,2R,10aS)-1-formyl-7-methoxy-1-methyl-3,9,10,10a-tetrahydro-2H-phenanthren-2-yl]butanoate
• CAS: 796850-86-7
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: HEJGBHOIBRJFIB-BUVFEPMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((1S,2R,10aS)-1-Formyl-7-methoxy-1-methyl-1,2,3,9,10,10a-hexahydro-phenanthren-2-yl)-butyric acid methyl ester 在 吡啶 、 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (3R,4aS,4bS,12aR)-8-Methoxy-4a-methyl-4-oxo-1,2,3,4,4a,4b,5,6,12,12a-decahydro-chrysene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Application of Chiral Cationic Catalysts to Several Classical Syntheses of Racemic Natural Products Transforms Them into Highly Enantioselective Pathways

  摘要：

  This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B-12 (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).

  DOI：

  10.1021/ja046154m
• 作为产物：
  描述：

  7-甲氧基-4-乙烯基-1,2-二氢萘 、 methyl (E)-6-methyl-7-oxohept-5-enoate 在 chiral oxazaborolidinium*Tf₂N^(1-) derivative 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 4-((1R,2S,10aR)-1-Formyl-7-methoxy-1-methyl-1,2,3,9,10,10a-hexahydro-phenanthren-2-yl)-butyric acid methyl ester 、 4-((1S,2R,10aS)-1-Formyl-7-methoxy-1-methyl-1,2,3,9,10,10a-hexahydro-phenanthren-2-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Application of Chiral Cationic Catalysts to Several Classical Syntheses of Racemic Natural Products Transforms Them into Highly Enantioselective Pathways

  摘要：

  This paper describes the application of chiral oxazaborolidinium cations of type 2 to various enantioselective Diels-Alder reactions that have served as early key steps for the syntheses of complex natural products. In the original syntheses these Diels-Alder reactions produced racemic adducts and led to racemic target molecules unless a separation of enantiomers by classical resolution was employed. By use of chiral catalysts of type 2, chiral products were obtained directly from Diels-Alder reactions of achiral components in excellent yield and enantioselectivity and with the mechanistically predicted absolute configuration. As a result, a number of classical syntheses could be converted to enantioselective versions, including (1) cortisone/cortisol (Merck/Sarett), (2) dendrobine (Kende), (3) vitamin B-12 (Eschenmoser), (4) myrocin C (Chu-Moyer/Danishefsky), (5) coriolin and hirsutene (Mehta), (6) dendrobatid 251F (Aube), (7) silphinene (Ito), and (8) nicandrenone core (Stoltz/Corey).

  DOI：

  10.1021/ja046154m