(R)-1-(2-methylnaphthalen-1-yl)-but-3-enyl acrylate | 1115246-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-(2-methylnaphthalen-1-yl)-but-3-enyl acrylate
• 英文别名: [(1R)-1-(2-methylnaphthalen-1-yl)but-3-enyl] prop-2-enoate
• CAS: 1115246-89-3
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: KSOHYUIIFTVOMT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(2-methylnaphthalen-1-yl)-but-3-enyl acrylate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以60%的产率得到(R)-6-(2-methylnaphthalen-1-yl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

  摘要：

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.069
• 作为产物：
  描述：

  2-甲基-1-萘醛 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 、 四氯化钛 、 三乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (R)-1-(2-methylnaphthalen-1-yl)-but-3-enyl acrylate
  参考文献：
  名称：

  6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

  摘要：

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.069

文献信息

• 6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties
  作者：Pınar Kasaplar、Özgür Yılmazer、Ali Çağır

  DOI：10.1016/j.bmc.2008.10.069

  日期：2009.1

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.