(4R)-4-(diphenylmethyl)-3-[3-(3',4',5'-trimethoxyphenyl)-2(E)-propenoyl]-2-oxazolidinone | 404953-14-6

• 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: (4R)-4-(diphenylmethyl)-3-[3-(3',4',5'-trimethoxyphenyl)-2(E)-propenoyl]-2-oxazolidinone
• 英文别名: (4R)-4-benzhydryl-3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 404953-14-6
• 化学式: C₂₈H₂₇NO₆
• 分子量: 473.525
• InChiKey: RIMOPVJWHCVYMD-FRFYRWIFSA-N

物化性质

• 沸点：
  606.6±65.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-(diphenylmethyl)-3-[3-(3',4',5'-trimethoxyphenyl)-2(E)-propenoyl]-2-oxazolidinone 在 lithium hydroxide 、 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 52.33h， 生成 (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 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (4R)-4-(diphenylmethyl)-3-[3-(3',4',5'-trimethoxyphenyl)-2(E)-propenoyl]-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

文献信息

• Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to &lt;i&gt;N&lt;/i&gt;-enoyl-4-diphenylmethyl-2-oxazolidinones
  作者：Mukund P. Sibi、Michael D. Johnson、T. Punniyamurthy

  DOI：10.1139/cjc-79-11-1546

  日期：——

  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.