(R)-2-(furan-2-yl)-2-((trimethylsilyl)oxy)propanenitrile | 860994-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (R)-2-(furan-2-yl)-2-((trimethylsilyl)oxy)propanenitrile
• 英文别名: 2-trimethylsilyloxy-2-furan-2-yl-propanenitrile；(2R)-2-(furan-2-yl)-2-trimethylsilyloxypropanenitrile
• CAS: 860994-95-2
• 化学式: C₁₀H₁₅NO₂Si
• 分子量: 209.32
• InChiKey: HNYXNBKIYVUNMS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙酰基呋喃 、 三甲基氰硅烷 在 C₃₈H₂₆LiO₅P 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 5.17h， 以75%的产率得到(R)-2-(furan-2-yl)-2-((trimethylsilyl)oxy)propanenitrile
  参考文献：
  名称：

  手性锂（I）磷酰苯酚催化锂与二氰基三甲基硅酸锂（IV）的对映选择性氰基硅烷化反应

  摘要：

  通过使用手性锂（I）磷酰苯氧基水合络合物作为酸/碱协同催化剂，开发了酮的高度对映选择性氰基硅烷化产品。由Me 3 SiCN / LiCN原位生成的五配位硅酸盐是一种极易反应的氰基试剂。描述了一个30克规模的反应和（+）-13-羟基异环celabenzine的关键前体的合成。

  DOI：

  10.1002/anie.201510682

文献信息

• Asymmetric cyanosilylation of ketones catalyzed by recyclable polymer-supported copper(II) salen complexes
  作者：Gurusamy Rajagopal、Shanmugam Selvaraj、Karuthamohamed Dhahagani

  DOI：10.1016/j.tetasy.2010.07.029

  日期：2010.9

  Various ketones have undergone asymmetric trimethylsilylcyanation at room temperature with (CH3)(3)SiCN (TMSCN) in the presence of a chiral-supported Cu(salen) complex and Ph3PO as the catalyst. Aromatic, aliphatic, and heterocyclic ketones have been converted into the corresponding cyanohydrin trimethylsilyl ethers in 83-96% yields with 52-84% ee. Several factors concerning the reactivity and enantioselectivity have been discussed. A double activation where Cu(salen) plays the role of Lewis acid and Ph3PO acts as a Lewis base is reported. Poly(ethylene glycol) monomethyl ether (MeO-PEG) has been used as a soluble support while JandaJel (JJ) and Merrifield (MF) resins served as insoluble supports. Each polymer is linked to the salen catalyst through a glutarate spacer. The soluble catalysts were recovered by precipitation with a suitable solvent while the insoluble catalysts were simply filtered from the reaction mixture. The JandaJel-attached Cu(salen) catalyst could be used for five cycles with the retention of efficiency and the Merrifield-bound Cu(salen) catalyst was found to loose activity with each use. (C) 2010 Published by Elsevier Ltd.
• Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide
  作者：Manabu Hatano、Katsuya Yamakawa、Tomoaki Kawai、Takahiro Horibe、Kazuaki Ishihara

  DOI：10.1002/anie.201510682

  日期：2016.3.14

  A highly enantioselective cyanosilylation of ketones was developed by using a chiral lithium(I) phosphoryl phenoxide aqua complex as an acid/base cooperative catalyst. The pentacoordinate silicate generated in situ from Me3SiCN/LiCN acts as an extremely reactive cyano reagent. Described is a 30 gram scale reaction and the synthesis of the key precursor to (+)‐13‐hydroxyisocyclocelabenzine.

  通过使用手性锂（I）磷酰苯氧基水合络合物作为酸/碱协同催化剂，开发了酮的高度对映选择性氰基硅烷化产品。由Me 3 SiCN / LiCN原位生成的五配位硅酸盐是一种极易反应的氰基试剂。描述了一个30克规模的反应和（+）-13-羟基异环celabenzine的关键前体的合成。