(4S)-4-[1-bis(3',4'-methylenedioxy-5'-methoxyphenyl)methyl]-butyrolactone | 404953-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (4S)-4-[1-bis(3',4'-methylenedioxy-5'-methoxyphenyl)methyl]-butyrolactone
• 英文别名: (4R)-4-[bis(7-methoxy-1,3-benzodioxol-5-yl)methyl]oxolan-2-one
• CAS: 404953-29-3
• 化学式: C₂₁H₂₀O₈
• 分子量: 400.385
• InChiKey: ZSECVURVFYIMHQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S)-4-[1-bis(3',4'-methylenedioxy-5'-methoxyphenyl)methyl]-butyrolactone 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以98%的产率得到(3S,4S)-3-methyl-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 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 26.33h， 生成 (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