methyl syn-4-hydroxy-2-methylene-3,4-diphenylbutanoate | 1170666-65-5

• 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: methyl syn-4-hydroxy-2-methylene-3,4-diphenylbutanoate
• 英文别名: Methyl 4-hydroxy-2-methylidene-3,4-diphenylbutanoate；methyl 4-hydroxy-2-methylidene-3,4-diphenylbutanoate
• CAS: 1170666-65-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: JGOQJSOPXHXQPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl syn-4-hydroxy-2-methylene-3,4-diphenylbutanoate 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲苯 为溶剂， 反应 5.33h， 生成 1-benzyl-5-methoxy-3-methyl-4,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts

  摘要：

  以 MBH 加合物为起点，我们开发出了多种 5-羟基-3-吡咯啉-2-酮衍生物的高效合成方法。此外，还证明了所制备的 5-羟基-3-吡咯啉-2-酮的一些合成适用性，包括合成内酰胺融合的四氢异喹啉。

  DOI：

  10.5012/bkcs.2012.33.5.1622
• 作为产物：
  描述：

  methyl 2-(bromomethyl)-3-phenylacrylate 、 苯甲醛 在 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 methyl syn-4-hydroxy-2-methylene-3,4-diphenylbutanoate
  参考文献：
  名称：

  Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts

  摘要：

  以 MBH 加合物为起点，我们开发出了多种 5-羟基-3-吡咯啉-2-酮衍生物的高效合成方法。此外，还证明了所制备的 5-羟基-3-吡咯啉-2-酮的一些合成适用性，包括合成内酰胺融合的四氢异喹啉。

  DOI：

  10.5012/bkcs.2012.33.5.1622

文献信息

• Factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against pancreatic cancer
  作者：P. Veeraraghavan Ramachandran、Matthew A. Helppi、Arlie L. Lehmkuhler、Jennifer M. Marchi、C. Max Schmidt、Michele T. Yip-Schneider

  DOI：10.1016/j.bmcl.2015.07.087

  日期：2015.10

  A systematic study to identify the factors influencing the cytotoxicity of a-methylene-c-hydroxy esters against three pancreatic cancer cell lines (Panc-1, MIA-PaCa-2, and BxPC-3) has established that, in addition to Michael acceptor abilities, the possibility to lactonize to alpha-methylene-gamma-butyrolactones is as important. The substitution pattern and the number of carbons between the hydroxy and ester moieties also influence the bio-activity. (C) 2015 Elsevier Ltd. All rights reserved.
• New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
  作者：Feng Jun-Tao、Wang De-Long、Wu Yong-Ling、Yan He、Zhang Xing

  DOI：10.1016/j.bmcl.2013.05.073

  日期：2013.8

  Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the alpha-methylene-gamma-butyrolactone ring, a natural pharmacophore. All structures were confirmed by H-1 and C-13 NMR, MS, and single-crystal X-ray diffraction analyses. The results of antifungal and cytotoxic activity indicated that the synthesized analogues showed significant inhibitory activity and limited selectivity. Compound 45 exhibited the highest antifungal activity with IC50 = 22.8 mu M but moderate cytotoxic activity with IC50 = 28.5 mu M (against BGC823 cell line) and 7.7 mu M (against HeLa cell line). Analysis of structure-activity relationships revealed that the incorporation of an aromatic ring into the beta, gamma positions of the lactone ring improved antifungal activity, and that the introduction of electron-withdrawing groups into the aromatic rings increased the activity compared with electron-donating groups. The above results identified 4-phenyl-3-phenyl-2-methylenebutyrolactone (33) as a lead scaffold for discovering and developing novel and improved crop-protection agents. (C) 2013 Elsevier Ltd. All rights reserved.
• SAFER, POTENT, AND FAST ACTING ANTIMICROBIAL AGENTS
  申请人：Purdue Research Foundation

  公开号：US20210317099A1

  公开（公告）日：2021-10-14

  The present invention generally relates to compounds, composition matters, and methods for the treatment of a patient with an infection caused by microorganisms, including bacterial, viral, and fungal infections. In particular, this disclosure relates to safe, highly potent and fast acting antimicrobial agents α-methylene and α-aminomethyl lactones, lactams, iminolactones, and iminolactams, thiolactones, thionolactones, thiolactams, and thionolactams having a formula of I, II, III, or IV, for the treatment of viral and bacterial infections, especially for infections caused by methicillin-resistant Staphylococcus aureus (MRSA).
• Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts
  作者：Cheol-Hee Lim、Sung-Hwan Kim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2012.33.5.1622

  日期：2012.5.20

  An efficient synthetic method of various 5-hydroxy-3-pyrrolin-2-one derivatives has been developed starting from the MBH adducts. In addition, some synthetic applicability of the prepared 5-hydroxy-3-pyrrolin-2-ones was demonstrated including the synthesis of lactam-fused tetrahydroisoquinolines.

  以 MBH 加合物为起点，我们开发出了多种 5-羟基-3-吡咯啉-2-酮衍生物的高效合成方法。此外，还证明了所制备的 5-羟基-3-吡咯啉-2-酮的一些合成适用性，包括合成内酰胺融合的四氢异喹啉。