(3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3'',4''-methylenedioxy-5''-methoxyphenyl))-propanoyl]-2-oxazolidinone | 404953-32-8

• 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: (3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3'',4''-methylenedioxy-5''-methoxyphenyl))-propanoyl]-2-oxazolidinone
• 英文别名: (3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxy-5"-methoxyphenyl))-propanoyl]-2-oxazolidinone
• CAS: 404953-32-8
• 化学式: C₃₆H₃₅NO₉
• 分子量: 625.675
• InChiKey: AFANVZXOZYZXLH-SXOMAYOGSA-N

物化性质

• 沸点：
  765.3±60.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3'',4''-methylenedioxy-5''-methoxyphenyl))-propanoyl]-2-oxazolidinone 在 lithium hydroxide 、 硼烷 、 双氧水 、 sodium hexamethyldisilazane 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 52.0h， 生成 (3R,4S,5R)-3-methyl-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxy-5"-methoxyphenyl)methyl]-butyrolactone
  参考文献：
  名称：

  Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to <i>N</i>-enoyl-4-diphenylmethyl-2-oxazolidinones

  摘要：

  A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in similar to 28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.

  DOI：

  10.1139/cjc-79-11-1546
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 正丁基锂 、 草酰氯 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 生成 (3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3'',4''-methylenedioxy-5''-methoxyphenyl))-propanoyl]-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to <i>N</i>-enoyl-4-diphenylmethyl-2-oxazolidinones

  摘要：

  A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in similar to 28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.

  DOI：

  10.1139/cjc-79-11-1546