ethyl (5E)-4-hydroxy-4-methyl-6-phenylhex-5-en-2-ynoate | 914359-54-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: ethyl (5E)-4-hydroxy-4-methyl-6-phenylhex-5-en-2-ynoate
• CAS: 914359-54-9
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: WHYDZBXAKYGROZ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (5E)-4-hydroxy-4-methyl-6-phenylhex-5-en-2-ynoate 在 喹啉 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以79%的产率得到5-methyl-5-styrylfuran-2(5H)-one
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

  摘要：

  The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the alpha,beta-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these alpha,beta-unsaturated styryl lactones, thereby further focusing the design of novel candidates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.044
• 作为产物：
  描述：

  苯甲醛 在 morpholinium trifluoroacetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (5E)-4-hydroxy-4-methyl-6-phenylhex-5-en-2-ynoate
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

  摘要：

  The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the alpha,beta-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these alpha,beta-unsaturated styryl lactones, thereby further focusing the design of novel candidates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.044

文献信息

• Conjugated Olefin Enabled Rollover Cyclometallation of Distant C‐H Bonds: Regioselective Annulation of <i>o</i>‐Alkenyl Phenols with Alkynes
  作者：Attunuri Nagireddy、Muniganti Naveen Kumar、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1002/chem.202303245

  日期：2023.12.14

  A regioselective rollover cyclometallation, assisted by conjugated olefin, is unveiled for the annulation of alkynes at two distant C−H bonds of o-alkenyl phenols. The annulation follows a concomitant cyclization rewarding a rare triple C−H functionalization. The reaction is also totally regioselective with an array of unsymmetrical alkynes, taking the leverage of an extended conjugation or a tertiary

  在共轭烯烃的辅助下，揭示了一种区域选择性翻转环金属化，用于在邻烯基酚的两个遥远的 C−H 键上实现炔烃的成环。环化伴随着环化，奖励罕见的三重 C−H 官能化。利用扩展共轭或叔羟基配位的杠杆作用，该反应对于一系列不对称炔烃也是完全区域选择性的。
• Efficient Synthesis of 1,3,5-Trisubstituted (Pyrrol-2-yl)acetic Acid Esters via Dual Nucleophilic Reactions of Sulfonamides or Carbamate with 4-Trimethyl-siloxy-(5<i>E</i>)-hexen-2-ynoates:  Lewis Acid Catalyzed S_N1 and Intramolecular Michael Addition
  作者：Teruhiko Ishikawa、Toshiaki Aikawa、Shinichiro Watanabe、Seiki Saito

  DOI：10.1021/ol0616485

  日期：2006.8.1

  Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.
• Pt-Catalyzed Pentannulations from In Situ Generated Metallo−Carbenoids Utilizing Propargylic Esters
  作者：B. A. Bhanu Prasad、Francis K. Yoshimoto、Richmond Sarpong

  DOI：10.1021/ja053192c

  日期：2005.9.1

  A highly selective and efficient Pt-catalyzed pentannulation reaction beginning from propargylic esters is described. The key to this reaction is the use of a PtCl2(PPh3)2/PhIO catalyst combination that allows the in situ generation of Pt-carbenoid intermediates, which lead to good yields (61-84%) of the desired pentannulated compounds.