(R)-3-羟基苯甲醛氰醇 | 10049-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (R)-3-羟基苯甲醛氰醇
• 英文名称: (R)-3-hydroxybenzaldehyde cyanohydrin
• 英文别名: D-3-Hydroxy-mandelsaeure-nitril；(2r)-2-Hydroxy-2-(3-hydroxyphenyl)acetonitrile
• CAS: 10049-64-6
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: ATGRXWCYTKIXIC-QMMMGPOBSA-N

物化性质

• 沸点：
  384.6±27.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氢氰酸 、 间羟基苯甲醛 以 乙醇 为溶剂， 生成 (R)-3-羟基苯甲醛氰醇
  参考文献：
  名称：

  Becker,W. et al., Angewandte Chemie, 1965, vol. 77, p. 1139

  摘要：

  DOI：

文献信息

• Process for preparing optically active cyanohydrins and secondary products
  申请人：Clariant GmbH

  公开号：US20020052523A1

  公开（公告）日：2002-05-02

  The present invention relates to a process for preparing optically active cyanohydrins of the formula (II), 1 by reacting an aldehyde of the formula (I) 2 with HCN in a water-immiscible organic solvent in the presence of water, in the absence or presence of a buffer, in the presence of a (R)-hydroxynitrile lyase, where X, Y and Z in formula (II) have the same meaning as in formula (I), independently of each other are identical or different and are H, F, Cl, Br, I, OH, O(C 1 -C 4 -alkyl), OCOCH 3 , NHCOCH 3 , NO 2 or C 1 -C 4 -alkyl.

  本发明涉及一种制备光学活性氰醇的方法，该氰醇的化学式为（II），通过在水不相溶的有机溶剂中，在水的存在下，在缓冲剂的存在或缺失下，以及（R）-羟基腈酶的存在下，将化学式为（I）的醛与HCN反应，其中化学式（II）中的X、Y和Z与化学式（I）中的含义相同，独立于彼此相同或不同，并且为H、F、Cl、Br、I、OH、O（C1-C4-烷基）、OCOCH3、NHCOCH3、NO2或C1-C4-烷基。
• Process for preparing an enzyme extract
  申请人：Clariant GmbH

  公开号：US20020052039A1

  公开（公告）日：2002-05-02

  The present invention relates to a process for preparing an (R)-hydroxynitrile lyase extract by extracting an (R)-hydroxynitrile lyase-containing natural product with water in the absence or presence of a buffer at a pH of 3.3 to 5.5.

  本发明涉及一种制备(R)-羟腈裂解酶提取物的工艺，其方法是在 pH 值为 3.3 至 5.5 的缓冲液不存在或存在的情况下，用水提取含(R)-羟腈裂解酶的天然产物。
• Matthews, Barry R.; Jackson, W. Roy; Jayatilake, Gamini S., Australian Journal of Chemistry, 1988, vol. 41, # 11, p. 1697 - 1710
  作者：Matthews, Barry R.、Jackson, W. Roy、Jayatilake, Gamini S.、Wilshire, Colin、Jacobs, Howard A.

  DOI：——

  日期：——
• 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.
• MATTHEWS, BARRY R.;JACKSON, W. ROY;JAYATILAKE, GAMINI S.;WILSHIRE, COLIN;+, AUSTRAL. J. CHEM., 41,(1988) N1, C. 1697-1709
  作者：MATTHEWS, BARRY R.、JACKSON, W. ROY、JAYATILAKE, GAMINI S.、WILSHIRE, COLIN、+

  DOI：——

  日期：——