2-羟基-2-(4-(2-丙烯氧基)苯基)乙腈 | 153225-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-羟基-2-(4-(2-丙烯氧基)苯基)乙腈
• 英文名称: 2-(4-allyloxyphenyl)-2-hydroxyacetonitrile
• 英文别名: (R)-2-hydroxy-2-(4-(2-propenyloxy)phenyl)acetonitrile；2-hydroxy-2-<4-(2-propenyloxy)phenyl>acetonitrile；(2R)-2-hydroxy-2-(4-prop-2-enoxyphenyl)acetonitrile
• CAS: 153225-88-8
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: XKRNDADVWIUTST-NSHDSACASA-N

物化性质

• 沸点：
  366.4±37.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-2-(4-(2-丙烯氧基)苯基)乙腈 在 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三正丁基氢锡 、 二异丁基氢化铝 、 溴化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.83h， 生成 地诺帕明
  参考文献：
  名称：

  光学活性氰醇的合成应用。羟酰胺，戊酰胺和爱琴碱，强心药多巴胺和支气管扩张剂沙丁胺醇的一些类似物的对映选择性合成

  摘要：

  天然羟酰胺，（-）-氨甲酰胺和（-）-aegeline以及强心药（-）-地巴胺已通过对位甲氧基或对位烯丙氧基苯甲醛通过合成的手性形式以高总收率（> 65％）的方式制备涉及醛的对映选择性氢氰化的序列。已经使用相似的化学方法以高收率和良好的对映体过量来制备支气管扩张剂（-）-沙丁胺醇的类似物。

  DOI：

  10.1016/s0040-4020(01)85686-6
• 作为产物：
  描述：

  对羟基苯甲醛 在 氢氧化钾 、 (3S,6S)-3-((1H-Imidazol-5-yl)methyl)-6-benzylpiperazine-2,5-dione 、 potassium iodide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成 2-羟基-2-(4-(2-丙烯氧基)苯基)乙腈
  参考文献：
  名称：

  Substituent effects on the enantioselective hydrocyanation of aryl aldehydes

  摘要：

  A detailed study of the dipeptide catalysed enantioselective hydrocyanation of a series of O-substituted 4-hydroxybenzaldehydes has shown that adverse steric effects can occur leading to low enantiomeric excess (e.e.) values when the substituent is long and flexible. Similar hydrocyanation of several derivatives of 3,4-dihydroxybenzaldehydes have been shown to give very variable values of e.e. Hydrocyanation of 3,5-dimethoxy and 3,4,5-trimethoxybenzaldehyde consistently gave low values of e.e.

  DOI：

  10.1016/0957-4166(94)80124-x

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。
• A synthesis of (−)-denopamine
  作者：Roger F.C. Brown、W.Roy Jackson、Tom D. McCarthy

  DOI：10.1016/s0957-4166(00)80062-2

  日期：1993.10

  The important cardiac drug, (-)-denopamine, has been synthesised in 68% overall yield from para-allyloxybenzaldehyde via (R)-2-hydroxy-2-[(2-propenyloxy)phenyl]acetonitrile
• Synthesis of the Adrenergic Bronchodilators (<i>R</i>)-Terbutaline and (<i>R</i>)-Salbutamol from (<i>R</i>)-Cyanohydrins¹
  作者：Franz Effenberger、Jürgen Jäger

  DOI：10.1021/jo970032d

  日期：1997.6.13

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.
• Synthetic applications of optically active cyanohydrins. Enantioselective syntheses of the hydroxyamides tembamide and aegeline, the cardiac drug denopamine, and some analogues of the bronchodilator salbutamol
  作者：Roger F.C. Brown、Andrew C. Donohue、W.Roy Jackson、Tom D. McCarthy

  DOI：10.1016/s0040-4020(01)85686-6

  日期：1994.1

  The natural hydroxyamides, (−)-tembamide and (−)-aegeline, and the cardiac drug (−) -denopamine have been prepared in homochiral form in good overall yield (>65%) from para - methoxy or para-allyloxybenzaldehyde by synthetic sequences involving entantioselective hydrocyanation of the aldehydes. Similar chemistry has been used to prepare analogues of the bronchodilator (−)-salbutamol both in high yield

  天然羟酰胺，（-）-氨甲酰胺和（-）-aegeline以及强心药（-）-地巴胺已通过对位甲氧基或对位烯丙氧基苯甲醛通过合成的手性形式以高总收率（> 65％）的方式制备涉及醛的对映选择性氢氰化的序列。已经使用相似的化学方法以高收率和良好的对映体过量来制备支气管扩张剂（-）-沙丁胺醇的类似物。
• Substituent effects on the enantioselective hydrocyanation of aryl aldehydes
  作者：Hyun J. Kim、W.Roy Jackson

  DOI：10.1016/0957-4166(94)80124-x

  日期：1994.8

  A detailed study of the dipeptide catalysed enantioselective hydrocyanation of a series of O-substituted 4-hydroxybenzaldehydes has shown that adverse steric effects can occur leading to low enantiomeric excess (e.e.) values when the substituent is long and flexible. Similar hydrocyanation of several derivatives of 3,4-dihydroxybenzaldehydes have been shown to give very variable values of e.e. Hydrocyanation of 3,5-dimethoxy and 3,4,5-trimethoxybenzaldehyde consistently gave low values of e.e.