(R)-2-(Trimethylsiloxy)pentannitril | 131298-17-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-2-(Trimethylsiloxy)pentannitril
• 英文别名: (2R)-2-trimethylsilyloxypentanenitrile
• CAS: 131298-17-4
• 化学式: C₈H₁₇NOSi
• 分子量: 171.315
• InChiKey: PYFCUTNREGLEBZ-MRVPVSSYSA-N

物化性质

• 沸点：
  85 °C(Press: 10 Torr)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(Trimethylsiloxy)pentannitril 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以58.1%的产率得到(S)-2-fluoropentanenitrile
  参考文献：
  名称：

  Preparation of (S)-fluoronitriles

  摘要：

  (S)-2-fluoronitriles (S)-4 are obtained in good chemical and high optical yields from (R)-cyanohydrins (R)-2 or (R)-cyanohydrin trimethylsilylethers (R)-3 by fluorination with DAST or by nucleophilic substitution of alpha-sulfonyloxynitriles (R)-6, 7 with fluoride on polymeric supports (Amberlyst A-26 F-) under inversion of configuration of the starting cyanohydrins.

  DOI：

  10.1016/s0957-4166(00)82327-7
• 作为产物：
  描述：

  三甲基氯硅烷 、 (R)-(+)-2-羟基戊腈 在 吡啶 作用下， 以 乙醚 为溶剂， 以60.9%的产率得到(R)-2-(Trimethylsiloxy)pentannitril
  参考文献：
  名称：

  Preparation of (S)-fluoronitriles

  摘要：

  (S)-2-fluoronitriles (S)-4 are obtained in good chemical and high optical yields from (R)-cyanohydrins (R)-2 or (R)-cyanohydrin trimethylsilylethers (R)-3 by fluorination with DAST or by nucleophilic substitution of alpha-sulfonyloxynitriles (R)-6, 7 with fluoride on polymeric supports (Amberlyst A-26 F-) under inversion of configuration of the starting cyanohydrins.

  DOI：

  10.1016/s0957-4166(00)82327-7

文献信息

• A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins
  作者：Samik Nanda、Yasuo Kato、Yasuhisa Asano

  DOI：10.1016/j.tet.2005.08.105

  日期：2005.11

  A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC

  从日本杏（Prunus mume）的种子中分离出一种新的羟腈裂解酶（HNL ）。该酶与从其他李属物种中分离的HNL具有相似的特性，并且是含FAD的酶。它接受大量非天然底物（苯甲醛及其变体）以添加HCN，从而以优异的光学和化学收率生产相应的氰醇。针对该酶开发了一种新的基于HPLC的对映选择性测定技术，该技术可促进在缓冲溶液（pH = 4.5）中将KCN添加到苯甲醛中。
• Effenberger, Franz; Gutterer, Beate; Ziegler, Thomas, Liebigs Annalen der Chemie, 1991, # 3, p. 269 - 273
  作者：Effenberger, Franz、Gutterer, Beate、Ziegler, Thomas

  DOI：——

  日期：——
• Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins
  作者：Jonathan J. Duffield、Andrew C. Regan

  DOI：10.1016/0957-4166(96)00059-6

  日期：1996.3

  An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method. (C) 1996 Elsevier Science Ltd
• Stereoselective synthesis of β-amino-γ-butyrolactones
  作者：Jürgen Roos、Franz Effenberger

  DOI：10.1016/s0957-4166(02)00437-8

  日期：2002.9

  A novel synthesis of optically active beta-amino-gamma-butyrolactones is described. O-Silylated (R)-cyanohydrins (R)-3 (derived from aldehydes 1 by (R)-hydroxynitrile lyase ((R)-PaHNL)-catalyzed addition of HCN) were reacted with allyl Grignard to give amino alcohols (4R,5S)-5 after reduction. In the addition of crotyl Grignard reagent, workup conditions are decisive for the formation of amino alcohol 8, which was isolated Lis a diastercoisomeric mixture the acetylated main diastereoisomer (3S,4R,5R)-10 was separated. Ozonolysis of the acetylated amino alcohols (4S,5R)-7a,b and (3S,4S,5R)-10 affords the aldehydes 12a-c, which were directly oxidized with CrO3 in dilute H2SO4 to yield the beta-acetamido-gamma-acetoxycarboxylic acids (3S,4R)-13a,b and (2R,3S,4R)-13c. Compounds 13 cyclized spontaneously Under acidic conditions to afford beta-acetamido-gamma-butyrolactones (4S,5R)-14a,b and (3R,4S,5R)-14c. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis, characterization and catalytic property of chiral oxo-vanadium (+)-pseudoephedrine complex supported on magnetic nanoparticles Fe3O4 in the cyanosilylation of carbonyl compounds
  作者：Amin Rostami、Bahareh Atashkar

  DOI：10.1016/j.catcom.2014.08.029

  日期：2015.1

  Vanadium complex of pseudoephedrine immobilized on magnetic nanoparticle Fe3O4(Pseudoephedrine) @MNPs] was prepared and characterized by UV-vis, SEM, XRD, TGA, EDX, FT-IR, AGFM and elemental analysis techniques. VO(Pseudoephedrine)@MNPs was found to catalyze the cyanosilylation of carbonyl compounds using TMSCN in good yields with 8-25% enantiomeric excesses under solvent-free conditions at room temperature. The catalyst was recycled up to 15 times with little loss of activity and enantioselectivity. (C) 2014 Elsevier B.V. All rights reserved.