6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one | 136801-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• 英文别名: 6-(2-Hydroxypropyl)-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 136801-79-1
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: QFQPMOQBTIOSKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin

  摘要：

  报告了一种新的合成策略，用于获得（±）-3-去氧根毒素（2）。这种合成方法比以前文献中报道的方法更高效，同时在C-7和C-2位置引入不同侧链的多功能性也更高。所得化合物（±）-2对草类杂草牛草具有植物毒性，与天然植物毒素根毒素（1）相当。因此，（±）-2可以作为比1更实用的合成替代品，用于牛草控制的生物除草剂。

  DOI：

  10.3390/molecules24173193
• 作为产物：
  描述：

  2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87%的产率得到6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Two lactone formation reactions from 1,3-dioxin-4-ones having hydroxyalkyl group at the 6-position: Difference in ring opening and closure

  摘要：

  Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1,3-dioxin-4-ones having 1-approximately 4-hydroxyalkyl group at the 6-position. Mechanism and scope of both methods have been clarified.

  DOI：

  10.1016/s0040-4020(01)86522-4

文献信息

• 3-METHYLIDENEOXAN-4-ONE COMPOUNDS AND SUBSTITUTED DERIVATIVES THEREOF AS INHIBITORS OF TELOMERASE
  申请人：NORTHWESTERN UNIVERSITY

  公开号：US20210070725A1

  公开（公告）日：2021-03-11

  Disclosed are 3-methylideneoxan-4-one compounds, derivatives thereof, and methods of their synthesis and methods of their use in treating a disease or disorder in a subject in need thereof, such as diseases and disorders that are associated with telomerase activity such as cancer. The disclosed compounds may be formulated in a pharmaceutical composition for treating diseases and disorders that are associated with telomerase activity such as cancer.

  本文披露了3-甲基亚氧杂环丙烯-4-酮化合物及其衍生物，以及它们的合成方法和在治疗患有疾病或障碍的受试者中的使用方法，例如与端粒酶活性相关的疾病和障碍，如癌症。披露的化合物可以制成药物组合物，用于治疗与端粒酶活性相关的疾病和障碍，如癌症。
• 3-methylideneoxan-4-one compounds and substituted derivatives thereof as inhibitors of telomerase
  申请人：NORTHWESTERN UNIVERSITY

  公开号：US11518750B2

  公开（公告）日：2022-12-06

  Disclosed are 3-methylideneoxan-4-one compounds, derivatives thereof, and methods of their synthesis and methods of their use in treating a disease or disorder in a subject in need thereof, such as diseases and disorders that are associated with telomerase activity such as cancer. The disclosed compounds may be formulated in a pharmaceutical composition for treating diseases and disorders that are associated with telomerase activity such as cancer.

  本发明公开了3-亚甲基氧杂环己烷-4-酮化合物、其衍生物及其合成方法和用于治疗有需要的受试者的疾病或失调的方法，例如与端粒酶活性相关的疾病和失调，如癌症。所公开的化合物可配制成药物组合物，用于治疗与端粒酶活性相关的疾病和紊乱，如癌症。
• 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.
• [EN] 4-AMINO-2H-PYRAN-2-ONE ANALOGS AS ANTICANCER AGENTS<br/>[FR] ANALOGUES 4-AMINO-2H-PYRAN-2-ONE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：UNIV NORTH CAROLINA

  公开号：WO2012061012A2

  公开（公告）日：2012-05-10

  Compounds of Formula I are described, along with methods of using such compounds for the treatment of cancer and pharmaceutical formulations thereof.
• Two lactone formation reactions from 1,3-dioxin-4-ones having hydroxyalkyl group at the 6-position: Difference in ring opening and closure
  作者：Masayuki Sato、Jun-ichi Sakaki、Yoshiaki Sugita、Sanae Yasuda、Hiroko Sakoda、Chikara Kaneko

  DOI：10.1016/s0040-4020(01)86522-4

  日期：1991.7

  Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1,3-dioxin-4-ones having 1-approximately 4-hydroxyalkyl group at the 6-position. Mechanism and scope of both methods have been clarified.