碳酸烯丙酯钠 | 18802-49-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: 碳酸烯丙酯钠
• 英文名称: sodium allyl carbonate
• 英文别名: carbonic acid monoallyl ester; sodium-salt；Kohlensaeure-monoallylester; Natrium-Salz；Sodium;prop-2-enyl carbonate
• CAS: 18802-49-8
• 化学式: C₄H₅O₃*Na
• 分子量: 124.072
• InChiKey: KSZMOOVMIIQFHA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.46
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碳酸烯丙酯钠 、 2-溴苯丙酮 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到carbonic acid allyl ester 1-methyl-2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a
• 作为产物：
  描述：

  烯丙醇钠 、 methylammonium carbonate 在 烯丙醇 作用下， 生成 碳酸烯丙酯钠
  参考文献：
  名称：

  Kurow, 1955, # 6, p. 99,101

  摘要：

  DOI：

文献信息

• Diallyl dicarbonate. A convenient reagent for the synthesis of allyl carbamates.
  作者：G'erard Sennyey、Gérard Barcelo、Jean-Pierre Senet

  DOI：10.1016/s0040-4039(01)81059-5

  日期：1987.1

  Diallyldicarbonate was prepared and used for the amino protection of various compounds including amino acids, amino sugars and nucleosides.

  制备了碳酸二烯丙酯，并将其用于各种化合物的氨基保护，包括氨基酸，氨基糖和核苷。
• Ligand Controlled Highly Regio- and Enantioselective Synthesis of α-Acyloxyketones by Palladium-Catalyzed Allylic Alkylation of 1,2-Enediol Carbonates
  作者：Barry M. Trost、Jiayi Xu、Thomas Schmidt

  DOI：10.1021/ja8038954

  日期：2008.9.10

  The palladium catalyzed decarboxylative asymmetric allylic alkylation of allyl 1,2-enediol carbonates 1 can decompose to either alpha-hydroxyketones 3 or alpha-hydroxyaldehydes 4. The product distribution is largely controlled by the ligand. Using Lnaph in DME we exclusively obtained the ketone product in good to excellent yields and high enantiomeric excesses. The reaction proceeds under extremely

  钯催化的 1,2-烯二醇碳酸酯 1 的脱羧不对称烯丙基烷基化可分解为 α-羟基酮 3 或 α-羟基醛 4。产物分布在很大程度上受配体控制。在 DME 中使用 Lnaph，我们专门获得了产率良好至极好的和高对映体过量的酮产品。反应在极其温和的条件下进行，因此我们可以有广泛的 OR 选择。除了常用的保护基团如 OAc 和 OPiv 外，还可以使用更多功能化的基团，如甲基丁-2-烯酰基，其下游过程可以提供其他合成有趣的结构。
• Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
  作者：Barry M. Trost、Jiayi Xu、Markus Reichle

  DOI：10.1021/ja067342a

  日期：2007.1.1

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.
• Kurow, 1955, # 6, p. 99,101
  作者：Kurow

  DOI：——

  日期：——