(R)-(+)-<(2-methoxy-iso-propyl)oxy>benzeneacetonitrile | 142429-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-<(2-methoxy-iso-propyl)oxy>benzeneacetonitrile
• 英文别名: (R)-2-[(2-methoxypropan-2-yl)oxy]-2-phenylacetonitrile；(R)-(+)-[(2-methoxy-iso-propyl)oxy]benzeneacetonitrile；(2R)-2-(2-methoxypropan-2-yloxy)-2-phenylacetonitrile
• CAS: 142429-13-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: VHLLIVHYEPSYTK-NSHDSACASA-N

物化性质

• 沸点：
  268.6±30.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-<(2-methoxy-iso-propyl)oxy>benzeneacetonitrile 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 (R)-2-(1-Methoxy-1-methyl-ethoxy)-2-phenyl-ethylideneamine
  参考文献：
  名称：

  Stereoselective synthesis of β-hydroxy-α-amino acids from chiral cyanohydrins.

  摘要：

  An efficient one-pot reduction-transimination-hydrocyanation synthesis of beta-hydroxy-alpha-cyanoamines 3 from optically active O-protected mandelonitrile (1) is described. These beta-hydroxy-alpha-cyanoamines were easily converted into optically active (2S,3R) beta-hydroxy-alpha-amino acids 6.

  DOI：

  10.1016/s0957-4166(00)80518-2
• 作为产物：
  描述：

  苯甲醛 在 4-二甲氨基吡啶 、 (R)-selective hydroxynitrile lyase 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 0.08h， 生成 (R)-(+)-<(2-methoxy-iso-propyl)oxy>benzeneacetonitrile
  参考文献：
  名称：

  化学酶流动级联反应，用于合成受保护的扁桃腈衍生物†

  摘要：

  化学酶法两步级联过程，两个步骤均具有不相容的反应条件，已成功地以连续流动的方式进行。使用基于膜的相分离模块，在单一流程中将氰醇的化学酶法水形成物与后续的有机相保护步骤结合在一起。通过合成九种受保护的氰醇衍生物，证明了我们装置的更广泛的适用性，所有这些衍生物均以良好的收率和高至优异的对映选择性获得。

  DOI：

  10.1039/c4ob02128b

文献信息

• A one-pot reduction-transimition-reduction synthesis of N-substituted β-ethanolamines from cyanohydrins
  作者：Peter Zandbergen、Adrianus M.C.H. van den Niewendijk、Johannes Brussee、Arne van der Gen、Chris G. Kruse

  DOI：10.1016/s0040-4020(01)88477-5

  日期：1992.1

  An efficient (74% – 97% yield) three-step one-pot synthesis of (R)-Halostachine and analogues from O-protected optically active cyanohydrins is described. The reaction sequence involves a DIBAL reduction of the nitrile to an imine, transimination to a secondary imine and sodium borohydride reduction to the corresponding N-substituted β-ethanolamine. Both O-protected as well as unprotected reaction

  描述了一种有效的（74％– 97％的收率）三步一锅合成法，由O保护的旋光性氰醇合成（R）-海洛沙汀及其类似物。反应顺序包括将腈进行DIBAL还原为亚胺，将氨基磺酸酯化为仲亚胺，然后将硼氢化钠还原为相应的N-取代的β-乙醇胺。既可以得到O-保护的反应产物，也可以得到未保护的反应产物。
• Direct conversion of chiral cyanohydrins to chiral nitrones by transimination
  作者：Edith Hulsbos、Jan Marcus、Johannes Brussee、Arne van der Gen

  DOI：10.1016/s0957-4166(97)00066-9

  日期：1997.4

  A new method for the preparation of enantiomerically pure N-benzyl nitrones is described. By using either a one-pot reduction-transimination or a one-pot Grignard addition-transimination sequence chiral O-protected alpha-hydroxynitriles can be converted into chiral aldo- and ketonitrones, respectively. (C) 1997 Elsevier Science Ltd.
• Stereoselective synthesis of β-hydroxy-α-amino acids from chiral cyanohydrins.
  作者：Peter Zandbergen、Johannes Brussee、Arne van der Gen、Chris G. Kruse

  DOI：10.1016/s0957-4166(00)80518-2

  日期：1992.6

  An efficient one-pot reduction-transimination-hydrocyanation synthesis of beta-hydroxy-alpha-cyanoamines 3 from optically active O-protected mandelonitrile (1) is described. These beta-hydroxy-alpha-cyanoamines were easily converted into optically active (2S,3R) beta-hydroxy-alpha-amino acids 6.
• Chemoenzymatic flow cascade for the synthesis of protected mandelonitrile derivatives
  作者：Mariëlle M. E. Delville、Kaspar Koch、Jan C. M. van Hest、Floris P. J. T. Rutjes

  DOI：10.1039/c4ob02128b

  日期：——

  A chemoenzymatic two-step cascade process, with both steps having incompatible reaction conditions, was successfully performed in continuous flow. The chemoenzymatic aqueous formation of cyanohydrins was integrated with a subsequent organic phase protection step in a single flow process utilising a membrane-based phase separation module. The wider applicability of our setup was demonstrated with the

  化学酶法两步级联过程，两个步骤均具有不相容的反应条件，已成功地以连续流动的方式进行。使用基于膜的相分离模块，在单一流程中将氰醇的化学酶法水形成物与后续的有机相保护步骤结合在一起。通过合成九种受保护的氰醇衍生物，证明了我们装置的更广泛的适用性，所有这些衍生物均以良好的收率和高至优异的对映选择性获得。
• Enantioselective Chemoenzymatic Synthesis of <i>cis-</i> and <i>trans</i>-2,5-Disubstituted Morpholines
  作者：Bas Ritzen、Steven Hoekman、Elena Durán Verdasco、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo1003295

  日期：2010.5.21

  A versatile synthesis of enantiomerically pure cis- and trans-2,5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction-transimination-reduction sequence followed by reduction and simultaneous protection provided cyclization precursors. Finally, cyclization and SmI2-mediated reductive detosylation completed the synthesis of cis- and trans-2,5-disubstituted morpholines in good yields and excellent diastereoselectivities.