(R)-5,6-dihydro-6-(naphthalen-2-yl)pyran-2-one | 1115246-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-5,6-dihydro-6-(naphthalen-2-yl)pyran-2-one
• 英文别名: (2R)-2-naphthalen-2-yl-2,3-dihydropyran-6-one
• CAS: 1115246-68-8
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: UNSFYAHOHKSKEM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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)-5,6-dihydro-6-(naphthalen-2-yl)pyran-2-one 、 乙硫醇 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  Michael acceptor properties of 6-bicycloaryl substituted (R)-5,6-dihydro-2H-pyran-2-ones

  摘要：

  The mechanism of action for alpha,beta-unsaturated lactones can be explained by their Michael acceptor properties. They have the potential of being covalently binding inhibitors by accepting nucleophiles from target proteins. In this work. Michael addition reactions of ethanethiol with 6-bicycloaryl substituted 5,6-dihydro-2H-pyran-2-ones were studied to explore the existence of such interactions. Three of the Michael addition products were isolated and tested over PC3 (human prostate cancer) and MCF-7 (human breast adenocarcinoma) cancer cell lines and no cytotoxicity was observed. It was revealed that biological activity depends on the existence of a Michael acceptor, but potency probably depends upon the 3D structure of the substituent on lactone ring. The primary chemical-quantum properties of the lactones were also calculated using the Spartan'08 computer program. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.06.005
• 作为产物：
  描述：

  phenyl 3-butenoate 、 2-萘甲醛 在 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 2-叔丁基-1,1,3,3-四甲基胍 、 二苯基甲氧基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 56.0h， 以85%的产率得到(R)-5,6-dihydro-6-(naphthalen-2-yl)pyran-2-one
  参考文献：
  名称：

  通过铜(I)-催化的直接乙烯基羟醛反应不对称合成α,β-不饱和δ-内酯

  摘要：

  通过铜（I）催化的 β,γ-不饱和酯和各种醛（包括芳香醛、杂芳香醛）的直接乙烯基醛醇反应 (DVAR)，实现了一种不对称合成手性 α,β-不饱和 δ-内酯的简单方法、α,β-不饱和醛和脂肪醛。对于芳香醛和杂芳香醛，需要由 DVAR、不饱和碳-碳双键从 (E)-形式异构化为 (Z)-形式以及随后的分子内酯交换组成的一锅反应，以获得中等至高产率和高对映选择性。对于 α,β-不饱和醛和脂肪族醛，DVAR 直接以中等收率和高对映选择性提供内酯。在 DVAR 中，各种功能组都具有良好的耐受性。而且，该方法很好地适用于分布在天然产物、天然产物衍生物和药物分子衍生物（托莫西汀和萘普生）中的醛基。机理研究表明，α-加成是可逆的且不受青睐，这说明了 DVAR 具有出色的区域选择性。提出通过去质子化产生的铜 (I)-二烯醇化物物质与烯丙基铜 (I) 物质形成平衡，烯丙基铜 (I) 物质与醛反应通过醛的催化不对称烯丙基化提供

  DOI：

  10.1021/jacs.8b07929

文献信息

• [EN] A NEW CLASS OF HIGHLY APOPTOTIC ANTI-CANCER AGENTS<br/>[FR] NOUVELLE CLASSE D'AGENTS ANTICANCÉREUX HAUTEMENT APOPTOTIQUES
  申请人：CAGIR ALI

  公开号：WO2011099947A1

  公开（公告）日：2011-08-18

  This invention relates to a list of apoptosis-inducers consisting of 6-bicycloaryl substituted 5,6-dihydro-2H-pyran-2-one derivatives. According to the present invention, the apoptosis-inducers trigger cell death by expression of a list of apoptotic genes, so they can be useful for the treatment of cancers, or other autoimmune diseases suffering from the lack of apoptosis such as viral infections, diabetes type I, or encephalomyelitis.

  这项发明涉及一种由6-双环芳基取代的5,6-二氢-2H-吡喁-2-酮衍生物组成的凋亡诱导剂列表。根据本发明，这些凋亡诱导剂通过表达一系列凋亡基因来触发细胞死亡，因此它们可以用于治疗癌症或其他由于凋亡缺乏而受影响的自身免疫疾病，如病毒感染、1型糖尿病或脑脊髓炎。
• 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.
• Asymmetric Synthesis of α,β-Unsaturated δ-Lactones through Copper(I)-Catalyzed Direct Vinylogous Aldol Reaction
  作者：Hai-Jun Zhang、Liang Yin

  DOI：10.1021/jacs.8b07929

  日期：2018.9.26

  for the asymmetric synthesis of chiral α,β-unsaturated δ-lactones was achieved by copper(I)-catalyzed direct vinylogous aldol reaction (DVAR) of β,γ-unsaturated esters and various aldehydes, including aromatic aldehydes, heteroaromatic aldehydes, α,β-unsaturated aldehydes, and aliphatic aldehydes. For aromatic and heteroaromatic aldehydes, a one-pot reaction consisting of DVAR, isomerization of the

  通过铜（I）催化的 β,γ-不饱和酯和各种醛（包括芳香醛、杂芳香醛）的直接乙烯基醛醇反应 (DVAR)，实现了一种不对称合成手性 α,β-不饱和 δ-内酯的简单方法、α,β-不饱和醛和脂肪醛。对于芳香醛和杂芳香醛，需要由 DVAR、不饱和碳-碳双键从 (E)-形式异构化为 (Z)-形式以及随后的分子内酯交换组成的一锅反应，以获得中等至高产率和高对映选择性。对于 α,β-不饱和醛和脂肪族醛，DVAR 直接以中等收率和高对映选择性提供内酯。在 DVAR 中，各种功能组都具有良好的耐受性。而且，该方法很好地适用于分布在天然产物、天然产物衍生物和药物分子衍生物（托莫西汀和萘普生）中的醛基。机理研究表明，α-加成是可逆的且不受青睐，这说明了 DVAR 具有出色的区域选择性。提出通过去质子化产生的铜 (I)-二烯醇化物物质与烯丙基铜 (I) 物质形成平衡，烯丙基铜 (I) 物质与醛反应通过醛的催化不对称烯丙基化提供
• Michael acceptor properties of 6-bicycloaryl substituted (R)-5,6-dihydro-2H-pyran-2-ones
  作者：Pınar Kasaplar、Özgür Yılmazer Çakmak、Ali Çağır

  DOI：10.1016/j.bioorg.2010.06.005

  日期：2010.10

  The mechanism of action for alpha,beta-unsaturated lactones can be explained by their Michael acceptor properties. They have the potential of being covalently binding inhibitors by accepting nucleophiles from target proteins. In this work. Michael addition reactions of ethanethiol with 6-bicycloaryl substituted 5,6-dihydro-2H-pyran-2-ones were studied to explore the existence of such interactions. Three of the Michael addition products were isolated and tested over PC3 (human prostate cancer) and MCF-7 (human breast adenocarcinoma) cancer cell lines and no cytotoxicity was observed. It was revealed that biological activity depends on the existence of a Michael acceptor, but potency probably depends upon the 3D structure of the substituent on lactone ring. The primary chemical-quantum properties of the lactones were also calculated using the Spartan'08 computer program. (C) 2010 Elsevier Inc. All rights reserved.