(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 | 796850-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (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
• CAS: 796850-96-9
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: WMTFIZILECESNI-XXULJNORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (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 在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (4aS,4bS,12aR)-8-Methoxy-4a-methyl-2,3,4a,4b,5,6,12,12a-octahydro-1H-chrysen-4-one
  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：

  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