(S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione | 303142-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione
• 英文别名: (S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione；(2S)-4-butyl-2,5-dimethyl-2-(phenylmethoxymethyl)cyclopent-4-ene-1,3-dione
• CAS: 303142-74-7
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: XRWYEOGKVMWINK-IBGZPJMESA-N

物化性质

• 沸点：
  417.1±34.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(S)-4-Butyl-2-hydroxymethyl-2,5-dimethyl-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0
• 作为产物：
  描述：

  (E,2S)-2-methyl-2-(phenylmethoxymethyl)oct-3-enal 在 四氧化锇 、 N-甲基吲哚酮 、 三氟化硼乙醚 、 sodium acetate 、 对甲苯磺酸 、 magnesium 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 159.91h， 生成 (S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0

文献信息

• Copper(I)-Catalyzed Asymmetric Desymmetrization: Synthesis of Five-Membered-Ring Compounds Containing All-Carbon Quaternary Stereocenters
  作者：Kohsuke Aikawa、Tatsuya Okamoto、Koichi Mikami

  DOI：10.1021/ja3032345

  日期：2012.6.27

  A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with

  开发了一种高度立体选择性催化烷基化序列，用于合成具有全碳四元立体中心的高度功能化和多功能的五元环化合物。因此，手性 Cu-亚磷酰胺催化剂实现了非手性环戊烯-1,3-二酮的对映选择性去对称化。可以在一锅操作中使用低催化剂负载量合成具有优异立体选择性的各种复杂的环戊烷衍生物。
• Ag(I)-Catalyzed Kinetic Resolution of Cyclopentene-1,3-diones
  作者：Hua-Chao Liu、Liang Wei、Rong Huang、Hai-Yan Tao、Hengjiang Cong、Chun-Jiang Wang

  DOI：10.1021/acs.orglett.8b01254

  日期：2018.6.15

  Ag(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides. This methodology shows good functional-group tolerance, delivering an array of synthetically valuable cyclopentene-1,3-diones with excellent stereoselectivity and generally high resolution efficiency (s = 48–226) accompanied by the biologically important fused pyrrolidine derivatives. Notably, this strategy allows facile access to the key

  通过Ag（I）催化的偶氮甲亚胺的不对称1,3-偶极环加成反应，已经开发出一种有效的动力学拆分消旋环戊烯-1,3-二酮。这种方法显示出良好的官能团耐受性，提供有价值的合成环戊烯-1,3-二酮的阵列具有优异的立体选择性和通常高分辨率效率（小号伴随生物学上重要的稠吡咯烷衍生物= 48-226）。值得注意的是，该策略允许轻松地获得关键中间体，以合成（+）-madindoline A和B。
• Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines
  作者：Seijiro Hosokawa、Kazuhiko Sekiguchi、Manabu Enemoto、Susumu Kobayashi

  DOI：10.1016/s0040-4039(00)00937-0

  日期：2000.8

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.