(2,3-cis,2,4-cis)-2-((morpholin-4-yl)methyl)-3,4-diphenylbutano-4-lactone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2,3-cis,2,4-cis)-2-((morpholin-4-yl)methyl)-3,4-diphenylbutano-4-lactone
• 英文别名: (3R,4S,5S)-3-(morpholin-4-ylmethyl)-4,5-diphenyloxolan-2-one
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: AIKJCZAUVKYLRC-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,3-cis,2,4-cis)-2-((morpholin-4-yl)methyl)-3,4-diphenylbutano-4-lactone 、 富马酸 以 乙醚 为溶剂， 反应 0.5h， 生成 (E)-but-2-enedioic acid;(3R,4S,5S)-3-(morpholin-4-ylmethyl)-4,5-diphenyloxolan-2-one
  参考文献：
  名称：

  Synthetic α-(aminomethyl)-γ-butyrolactones and their anti-pancreatic cancer activities

  摘要：

  Aminated alpha-methylene-c-butyrolactones, which are readily synthesized with facile control of the diastereoisomerism, provide an economical and commercially-viable alternative to the use of aminated natural products. These aminoloactones, which exhibit excellent activity against three pancreatic cancer cell lines when measured at 10 mu M-Panc-1, MIA PaCa-2, and BxPC-3-and are comparable to or better than parthenolide and dimethylaminoparthenolide (DMAPT, LC-1). It has also been shown that there is an effect on the biological activity depending on the identity of the amine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.065
• 作为产物：
  描述：

  吗啉 、 cis-2-methylene-3,4-diphenylbutano-4-lactone 以91%的产率得到(2,3-cis,2,4-cis)-2-((morpholin-4-yl)methyl)-3,4-diphenylbutano-4-lactone
  参考文献：
  名称：

  Synthetic α-(aminomethyl)-γ-butyrolactones and their anti-pancreatic cancer activities

  摘要：

  Aminated alpha-methylene-c-butyrolactones, which are readily synthesized with facile control of the diastereoisomerism, provide an economical and commercially-viable alternative to the use of aminated natural products. These aminoloactones, which exhibit excellent activity against three pancreatic cancer cell lines when measured at 10 mu M-Panc-1, MIA PaCa-2, and BxPC-3-and are comparable to or better than parthenolide and dimethylaminoparthenolide (DMAPT, LC-1). It has also been shown that there is an effect on the biological activity depending on the identity of the amine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.065

文献信息

• Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization
  作者：P. Veeraraghavan Ramachandran、Daniel R. Nicponski

  DOI：10.1039/c4cc05765a

  日期：——

  An auto-catalytic domino reaction involving an aza-Michael reaction, proton transfer, and lactonization furnishing α-aminomethyl-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

  一种涉及aza-Michael反应、质子转移和内酯化的自催化多米诺反应，以近定量的收率和优秀的对映选择性提供了α-氨基甲基-γ-丁内酯。

• Synthetic α-(aminomethyl)-γ-butyrolactones and their anti-pancreatic cancer activities
  作者：P. Veeraraghavan Ramachandran、Daniel R. Nicponski、Hari N.G. Nair、Matthew A. Helppi、Pravin D. Gagare、C. Max Schmidt、Michele T. Yip-Schneider

  DOI：10.1016/j.bmcl.2013.09.065

  日期：2013.12

  Aminated alpha-methylene-c-butyrolactones, which are readily synthesized with facile control of the diastereoisomerism, provide an economical and commercially-viable alternative to the use of aminated natural products. These aminoloactones, which exhibit excellent activity against three pancreatic cancer cell lines when measured at 10 mu M-Panc-1, MIA PaCa-2, and BxPC-3-and are comparable to or better than parthenolide and dimethylaminoparthenolide (DMAPT, LC-1). It has also been shown that there is an effect on the biological activity depending on the identity of the amine. (C) 2013 Elsevier Ltd. All rights reserved.