2,2-dimethyl-6-(2-oxo-2-cyclohexyl)-4H-1,3-dioxin-4-one | 1027985-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-6-(2-oxo-2-cyclohexyl)-4H-1,3-dioxin-4-one
• 英文别名: 6-(2-Cyclohexyl-2-oxoethyl)-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 1027985-96-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: SVWINQKPOOXLDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-(2-oxo-2-cyclohexyl)-4H-1,3-dioxin-4-one 以 甲苯 为溶剂， 以60 %的产率得到6-cyclohexyl-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Bi(OTf)3-促进羟基吡喃酮和不饱和γ-酮酯的级联成环，用于构建多环桥联吡喃并呋喃并吡喃酮

  摘要：

  提出了一种通过铋（ III ）催化羟基吡喃酮和不饱和γ-酮酯的级联环化构建复杂三维多环桥联色并呋喃并吡喃酮和吡喃并呋喃吡喃酮（与生物活性天然产物密切相关）的有效方案。这一过程涉及分子间迈克尔加成、分子内半缩酮化、内酯化、形成一个 C-C 键和两个 C-O 键、环和连续的立体中心。

  DOI：

  10.1039/d3ob01862h
• 作为产物：
  描述：

  2,2-Dimethyl-6-trimethylsilyloxy-1,3-dioxin-4-one 在 四氯化钛 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-dimethyl-6-(2-oxo-2-cyclohexyl)-4H-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

• A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones
  作者：Rick C. Betori、Eric R. Miller、Karl A. Scheidt

  DOI：10.1002/adsc.201700095

  日期：2017.4.3

  A novel biocatalytic system to access a wide variety of β‐hydroxydioxinones from β‐ketodioxinones employing commercial engineered ketoreductases has been developed. This practical system provides a remarkably straightforward solution to limitations in accessing certain chemical scaffolds common in β‐hydroxydioxinones that are of great interest due to their diversification capabilities. A few highlights

  已经开发出一种新型生物催化系统，可使用商业工程酮还原酶从 β-酮二恶酮中获取多种 β-羟基二恶酮。这个实用的系统为获取β-羟基二恶英酮中常见的某些化学支架的限制提供了一种非常简单的解决方案，这些化学支架由于其多样化能力而备受关注。该系统的一些亮点是它具有高产率、高对映选择性且无需色谱法。我们展示了广泛的基质范围和高度的可扩展性。
• 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%）。
• 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.
• Bi(OTf)₃-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones
  作者：Akshay B. Rathod、Balasaheb R. Borade、Pooja I. Sambherao、Ravindar Kontham

  DOI：10.1039/d3ob01862h

  日期：——

  three dimensional polycyclic bridged chromano-furopyranones and pyrano-furopyranones (closely related to bioactive natural products) via bismuth(III)-catalyzed cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters is presented. This process involves intermolecular Michael addition, intramolecular hemiketalization, lactonization, formation of one C–C bond and two C–O bonds, rings, and contiguous

  提出了一种通过铋（ III ）催化羟基吡喃酮和不饱和γ-酮酯的级联环化构建复杂三维多环桥联色并呋喃并吡喃酮和吡喃并呋喃吡喃酮（与生物活性天然产物密切相关）的有效方案。这一过程涉及分子间迈克尔加成、分子内半缩酮化、内酯化、形成一个 C-C 键和两个 C-O 键、环和连续的立体中心。