5-(cyclopropylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 862122-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(cyclopropylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-(cyclopropylmethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 862122-96-1
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: AOZJTRWLNDXQTN-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solv: hexane (110-54-3))
• 沸点：
  421.1±38.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  5-(cyclopropylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 哌啶 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization

  摘要：

  A series of 2,5-disubstituted-thiazolidine-2,4-dione analogs based on the newly identified lead 1, a potential anticancer agent via the inhibition of the Raf/MEK/extracellular signal regulated kinase (ERK) and phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades, were synthesized and biologically characterized. A new lead structure, 15, was identified to have improved anti-proliferative activities in U937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U937 cells at the S-phase. Furthermore, Western blot analysis demonstrated a correlation of the anti-proliferative activity and blockade of the Raf/MEK/ERK and PI3K/Akt signaling pathways. Collectively, these results strongly encourage further optimization of 15 as a new lead with multi-target properties to develop more potent compounds as anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.031
• 作为产物：
  描述：

  环丙基溴化镁 、 5-(二甲氨基亚甲基)-2,2-二甲基-1,3-二氧己环-4,6-二酮 以 四氢呋喃 为溶剂， 反应 1.0h， 以51%的产率得到5-(cyclopropylmethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  催化、对映选择性、共轭炔烃加成

  摘要：

  我们记录了铜催化的对映选择性共轭加成，涉及直接使用末端乙炔，该乙炔进行原位金属化。苯乙炔与 Meldrum 酸衍生受体的加成反应在水性介质中进行，无需借助惰性气氛。对映选择性过程的成功是通过使用一类新的方便访问的 P，N 配体，我们称之为 PINAP 实现的。这些模块化配体对允许优化反应的许多电子和空间修饰有响应。

  DOI：

  10.1021/ja052411r

文献信息

• Monophosphine compound, transition metal complex thereof and production method of optically active compound using the complex as asymmetric catalyst
  申请人：Carreira M. Erick

  公开号：US20050277772A1

  公开（公告）日：2005-12-15

  The present invention provides a compound represented by the formula (I): wherein ring A is void or a benzene ring optionally having substituent(s), R 1 and R 2 are each independently a phenyl group optionally having substituent(s), a cyclohexyl group and the like, R 3 and R 4 are each independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group and the like, and X is a residue represented by —OR 5 or —NHR 6 wherein R 5 and R 6 are a lower alkyl group optionally having substituent(s), an aralkyl group optionally having substituent(s) and the like, a asymmetric transition metal complex containing the compound as a ligand and a production method of optically active compound using the complex as an asymmetric catalyst.

  本发明提供了一种由以下式（I）表示的化合物： 其中环A为空或是一个苯环，可选地具有取代基，R1和R2分别独立地是一个苯基，可选地具有取代基，一个环己基等，R3和R4分别独立地是一个氢原子，一个卤原子，一个低碳基团，一个低碳氧基团等，X是由—OR5或—NHR6表示的残基，其中R5和R6是一个低碳基团，可选地具有取代基，一个芳基烷基团，可选地具有取代基等，一种含有该化合物作为配体的不对称过渡金属配合物以及使用该配合物作为不对称催化剂的光学活性化合物的生产方法。
• CuI-Catalyzed Conjugate Addition of Ethyl Propiolate
  作者：Shinji Fujimori、Erick M. Carreira

  DOI：10.1002/anie.200701098

  日期：2007.6.25
• Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls
  作者：James Giarrusso、Dung T. Do、Jeffrey S. Johnson

  DOI：10.1021/acs.orglett.7b01225

  日期：2017.6.16

  The diastereoconvergent synthesis of spirocyclic endoperoxides using a Meldrum's acid scaffold has been accomplished by employing readily available feedstock Chemicals. Site selective C-H oxidation of the bis(beta-dicarbonyl) substrates was performed using, elemental oxygen as the stoichiometric oxidant and a commercial Cu(II) catalyst. Sequential hydrogenolysis and ionic reduction of these-endoperoxides provided fully substituted tetrahydrofurans in high-yields and diastereoselectivity.
• US7790882B2
  申请人：——

  公开号：US7790882B2

  公开（公告）日：2010-09-07
• 3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization
  作者：Kai Liu、Wei Rao、Hardik Parikh、Qianbin Li、Tai L. Guo、Steven Grant、Glen E. Kellogg、Shijun Zhang

  DOI：10.1016/j.ejmech.2011.10.031

  日期：2012.1

  A series of 2,5-disubstituted-thiazolidine-2,4-dione analogs based on the newly identified lead 1, a potential anticancer agent via the inhibition of the Raf/MEK/extracellular signal regulated kinase (ERK) and phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades, were synthesized and biologically characterized. A new lead structure, 15, was identified to have improved anti-proliferative activities in U937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U937 cells at the S-phase. Furthermore, Western blot analysis demonstrated a correlation of the anti-proliferative activity and blockade of the Raf/MEK/ERK and PI3K/Akt signaling pathways. Collectively, these results strongly encourage further optimization of 15 as a new lead with multi-target properties to develop more potent compounds as anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.