6-(2-Cyclohexyl-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxin-4-one | 412277-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2-Cyclohexyl-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 412277-09-9
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: QHCHLGUCAXLVCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-Cyclohexyl-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxin-4-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 6-cyclohexyl-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  通过添加乙酰乙酸酯等价物、戴斯-马丁氧化和随后的环化从醛中合成 6-取代的 4-羟基-2-吡喃酮

  摘要：

  描述了一种从醛1合成6-取代的4-羟基-2-吡喃酮2的三步程序。向相应的醛中加入了一种乙酰乙酸酯等效物3（10个例子）进行维尼洛戈斯Mukaiyama aldol加成（72-99%）。中间醇4通过Dess-Martin方法被氧化为酮5（67%-量）。最后对化合物5进行热环化反应，得到了目标化合物2（61-92%；整体转换率为40-85%）。

  DOI：

  10.1055/s-2001-18759
• 作为产物：
  描述：

  2,2-Dimethyl-6-trimethylsilyloxy-1,3-dioxin-4-one 、 环己烷基甲醛 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 6-(2-Cyclohexyl-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxin-4-one
  参考文献：
  名称：

  Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

  摘要：

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.084

文献信息

• Synthesis of 6-Substituted 4-Hydroxy-2-pyrones from Aldehydes by Addition of an Acetoacetate Equivalent, Dess-Martin Oxidation and Subsequent Cyclization
  作者：Thorsten Bach、Stefan Kirsch

  DOI：10.1055/s-2001-18759

  日期：——

  A three step procedure for the synthesis of 6-substituted 4-hydroxy-2-pyrones 2 from aldehydes 1 is described. An acetoacetate equivalent 3 was added to the corresponding aldehyde (10 examples) in a vinylogous Mukaiyama aldol addition (72-99%). The intermediate alcohols 4 were oxidized to the ketones 5 using the Dess-Martin method (67%-quant.). A final thermal cyclization of compounds 5 yielded the title compounds 2 (61-92%; 40-85% overall).

  描述了一种从醛1合成6-取代的4-羟基-2-吡喃酮2的三步程序。向相应的醛中加入了一种乙酰乙酸酯等效物3（10个例子）进行维尼洛戈斯Mukaiyama aldol加成（72-99%）。中间醇4通过Dess-Martin方法被氧化为酮5（67%-量）。最后对化合物5进行热环化反应，得到了目标化合物2（61-92%；整体转换率为40-85%）。
• Stereoselective Synthesis of Tetrahydropyran-4-ones from Dioxinones Catalyzed by Scandium(III) Triflate
  作者：William J. Morris、Daniel W. Custar、Karl A. Scheidt

  DOI：10.1021/ol050093v

  日期：2005.3.1

  [reaction: see text] A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and beta-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in

  [反应：见正文]已发现三氟甲磺酸scan催化醛与β-羟基二恶英酮之间的非对映选择性环化。该过程利用了二恶英酮核心中嵌入的烯醇醚的未开发的亲核性。可以从所得环化反应中分离出双环化合物，或者可以直接添加醇盐亲核试剂。该原位加成使二恶英酮环断裂，并以高收率和高非对映选择性递送3-羧基取代的四氢吡喃-4-酮。
• Efficient and practical catalytic vinylogous aldol reaction of dioxinone-derived silyl dienol ethers with aromatic aldehydes
  作者：Thierry Ollevier、Valerie Desyroy、Cristian Catrinescu、Raphael Wischert

  DOI：10.1016/j.tetlet.2006.10.084

  日期：2006.12

  Vinylogous Mukaiyama-aldol reaction was realized by use of dioxinone-derived silyl dienol ethers and various aldehydes in the presence of highly catalytic amounts of bismuth triflate. The reaction proceeds rapidly and affords the corresponding β-hydroxy-1,3-dioxin-4-ones in very good to excellent yields (up to 98%).

  在高催化量的三氟甲磺酸铋的存在下，通过使用二恶英酮衍生的甲硅烷基二烯醇醚和各种醛类，可以实现乙烯基类的Mukaiyama-aldol反应。反应进行得很快，并以非常好的至极好的产率（高达98％）提供了相应的β-羟基-1，3-二恶英-4-酮。
• Highly Stereoselective Brønsted Acid Catalyzed Synthesis of Spirooxindole Pyrans
  作者：Jingqi Wang、Erika A. Crane、Karl A. Scheidt

  DOI：10.1021/ol200987c

  日期：2011.6.17

  A Bronsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a beta-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.
• Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity
  作者：Yizhou Dong、Kyoko Nakagawa-Goto、Chin-Yu Lai、Susan L. Morris-Natschke、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.02.084

  日期：2011.4

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.