(4(1S),4S)-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)methyl]-butyrolactone | 404953-40-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (4(1S),4S)-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)methyl]-butyrolactone
• CAS: 404953-40-8
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: SYNAOFYIPWJJMR-XOBRGWDASA-N

物化性质

• 沸点：
  553.6±50.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4(1S),4S)-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)methyl]-butyrolactone 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3S,4S,5R)-3-methyl-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)methyl]-butyrolactone 、 (3R,4S,5R)-3-methyl-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)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 lithium hydroxide 、 正丁基锂 、 草酰氯 、 硼烷 、 双氧水 、 sodium hexamethyldisilazane 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 51.33h， 生成 (4(1S),4S)-4-[1,1-(3',4',5'-trimethoxyphenyl)-(3",4"-methylenedioxyphenyl)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