(3(2S),4R)-4-(diphenylmethyl)-3-[bis-(3',4'-methylenedioxy-5'-methoxyphenyl)-methyl]-(4-oxo-butyric acid tert-butyl ester)-2-oxazolidinone | 404953-23-7

• 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(2S),4R)-4-(diphenylmethyl)-3-[bis-(3',4'-methylenedioxy-5'-methoxyphenyl)-methyl]-(4-oxo-butyric acid tert-butyl ester)-2-oxazolidinone
• 英文别名: tert-butyl (3R)-3-[(4R)-4-benzhydryl-2-oxo-1,3-oxazolidine-3-carbonyl]-4,4-bis(7-methoxy-1,3-benzodioxol-5-yl)butanoate
• CAS: 404953-23-7
• 化学式: C₄₁H₄₁NO₁₁
• 分子量: 723.777
• InChiKey: PWVUNJQULKLYBJ-WDYNHAJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3(2S),4R)-4-(diphenylmethyl)-3-[bis-(3',4'-methylenedioxy-5'-methoxyphenyl)-methyl]-(4-oxo-butyric acid tert-butyl ester)-2-oxazolidinone 在 lithium aluminium tetrahydride 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以74%的产率得到(4S)-4-[1-bis(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：

  4-甲氧基-6-溴-1,3-苯并二噁茂 在 sodium hexamethyldisilazane 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 6.33h， 生成 (3(2S),4R)-4-(diphenylmethyl)-3-[bis-(3',4'-methylenedioxy-5'-methoxyphenyl)-methyl]-(4-oxo-butyric acid tert-butyl ester)-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