(4S)-4-[1-bis(3',4',5'-trimethoxyphenyl)methyl]-butyrolactone | 136890-72-7

• 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: (4S)-4-[1-bis(3',4',5'-trimethoxyphenyl)methyl]-butyrolactone
• 英文别名: (3R)-3-[bis(30,40,50-trimethoxyphenyl)methyl]butyrolactone
• CAS: 136890-72-7
• 化学式: C₂₃H₂₈O₈
• 分子量: 432.471
• InChiKey: ASDGKPRCZQXOKD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4S)-4-[1-bis(3',4',5'-trimethoxyphenyl)methyl]-butyrolactone 在 palladium on activated charcoal 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 苯 为溶剂， 反应 17.0h， 生成 (3R,4S)-3-methyl-4-[1-bis(3',4',5'-trimethoxyphenyl)methyl]-butyrolactone
  参考文献：
  名称：

  一种立体选择性方法对生物活性secolignans的研究：胡椒粉蛋白C及其类似物的合成

  摘要：

  描述了对secolignans的立体选择性方法。关键的合成策略涉及不对称的醛醇缩合反应，以控制目标secolignans的β-碳上立体中心的产生。在目前的工作中，成功地以高收率和高立体选择性合成了佩珀罗明C及其类似物，即2,6-二氢氢化佩珀罗明C和2-表位佩珀罗明C。

  DOI：

  10.1016/j.tet.2014.07.101
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 sodium hexamethyldisilazane 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 30.33h， 生成 (4S)-4-[1-bis(3',4',5'-trimethoxyphenyl)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

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.
• A stereoselective approach to bioactive secolignans: synthesis of peperomin C and its analogues
  作者：Darunee Soorukram、Jaray Panmuang、Patoomratana Tuchinda、Chutima Kuhakarn、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1016/j.tet.2014.07.101

  日期：2014.10

  A stereoselective approach to secolignans is described. The key synthetic strategy involves an asymmetric aldol reaction to control the creation of the stereogenic center at the β-carbon of the target secolignans. In the present work, peperomin C and its analogues, i.e., 2,6-didehydropeperomin C and 2-epi-peperomin C were successfully synthesized in good yields with high stereoselectivities.

  描述了对secolignans的立体选择性方法。关键的合成策略涉及不对称的醛醇缩合反应，以控制目标secolignans的β-碳上立体中心的产生。在目前的工作中，成功地以高收率和高立体选择性合成了佩珀罗明C及其类似物，即2,6-二氢氢化佩珀罗明C和2-表位佩珀罗明C。