di-tert-butyl 2-(3-methylbutylidene)malonate | 1072808-16-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: di-tert-butyl 2-(3-methylbutylidene)malonate
• 英文别名: Ditert-butyl 2-(3-methylbutylidene)propanedioate；ditert-butyl 2-(3-methylbutylidene)propanedioate
• CAS: 1072808-16-2
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: RIJVPURBHPMWPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  di-tert-butyl 2-(3-methylbutylidene)malonate 、 [(苯基甲亚基)氨基]乙酸甲酯 在 silver(I) acetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,5S)-4,4-di-tert-butyl 2-methyl 3-isobutyl-5-phenylpyrrolidine-2,4,4-tricarboxylate
  参考文献：
  名称：

  exo-Selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkylidene malonates catalyzed by AgOAc/TF-BiphamPhos

  摘要：

  首次报道了银乙酸盐/TF-BiphamPhos催化的烷基烯基美克酸酯与肟亚胺负电荷的exo选择性不对称1,3-双极环加成反应，具有良好的产率以及良好到优异的对映体/非对映体选择性。

  DOI：

  10.1039/b919625k
• 作为产物：
  描述：

  丙二酸二叔丁酯 、 异戊醛 在 吡啶 、 四氯化钛 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 以74%的产率得到di-tert-butyl 2-(3-methylbutylidene)malonate
  参考文献：
  名称：

  Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates

  摘要：

  An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

  DOI：

  10.1021/ja805680z

文献信息

• Phase-Transfer-Catalyzed Asymmetric Conjugate Cyanation of Alkylidenemalonates with KCN in the Presence of a Brønsted Acid Additive
  作者：Yan Liu、Seiji Shirakawa、Keiji Maruoka

  DOI：10.1021/ol400143m

  日期：2013.3.15

  Highly enantioselective conjugate cyanation of alkylidenemalonates with KCN was achieved under mild phase-transfer conditions with a bifunctional phase-transfer catalyst. The effect of Brønsted acid additives was examined based on the hypothetical catalytic cycle, and the Brønsted acid additive was found to be essential to promote the conjugate cyanation efficiently.

  在温和的相转移条件下，使用双功能相转移催化剂可实现亚烷基丙二酸酯与KCN的高度对映选择性共轭氰化。基于假设的催化循环检查了布朗斯台德酸添加剂的效果，发现布朗斯台德酸添加剂对于有效地促进共轭氰化是必不可少的。
• exo-Selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkylidene malonates catalyzed by AgOAc/TF-BiphamPhos
  作者：Zhi-Yong Xue、Tang-Lin Liu、Zhou Lu、He Huang、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1039/b919625k

  日期：——

  The first exo-selective asymmetric 1,3-dipolar cycloaddition of alkylidene malonates with azomethine ylides catalyzed by AgOAc/TF-BiphamPhos has been reported in good yields and good to excellent enantio-/diastereoselectivities.

  首次报道了银乙酸盐/TF-BiphamPhos催化的烷基烯基美克酸酯与肟亚胺负电荷的exo选择性不对称1,3-双极环加成反应，具有良好的产率以及良好到优异的对映体/非对映体选择性。
• Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates
  作者：Qin Liu、Stéphane Perreault、Tomislav Rovis

  DOI：10.1021/ja805680z

  日期：2008.10.29

  An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.