(3R)-3-羟基丁腈 | 125103-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R)-3-羟基丁腈
• 中文别名: (R)-(-)-3-羟基丁腈
• 英文名称: (R)-3-hydroxybutanonitrile
• 英文别名: 3-hydroxybutyronitrile；(R)-3-hydroxybutanenitrile；(3R)-3-hydroxybutanenitrile
• CAS: 125103-95-9
• 化学式: C₄H₇NO
• 分子量: 85.1057
• InChiKey: BYJAJQGCMSBKPB-SCSAIBSYSA-N

物化性质

• 沸点：
  217℃
• 密度：
  0.991
• 闪点：
  85℃
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (3R)-3-羟基丁腈 、 乙酰氯 在 吡啶 作用下， 生成 (R)-acetoxybutyronitrile
  参考文献：
  名称：

  Enhanced Enantioselectivity of the Lipase-Catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol

  摘要：

  研究发现，L-甲硫醇（L-MetOH）是一种能有效提高脂肪酶催化解水反应对映选择性的添加剂。实验发现，L-MetOH促进了(R)-3-乙酰氧基丁腈（1）的酶催化解水反应，而抑制了(S)-1的反应。

  DOI：

  10.1246/bcsj.64.624
• 作为产物：
  描述：

  (+/-)-3-<(methylthio)acetoxy>butyronitrile 反应 6.0h， 以25%的产率得到(3R)-3-羟基丁腈
  参考文献：
  名称：

  Enhanced Enantioselectivity of the Lipase-Catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol

  摘要：

  研究发现，L-甲硫醇（L-MetOH）是一种能有效提高脂肪酶催化解水反应对映选择性的添加剂。实验发现，L-MetOH促进了(R)-3-乙酰氧基丁腈（1）的酶催化解水反应，而抑制了(S)-1的反应。

  DOI：

  10.1246/bcsj.64.624

文献信息

• Process Optimisation Studies and Aminonitrile Substrate Evaluation of <i>Rhodococcus erythropolis</i> SET1, A Nitrile Hydrolyzing Bacterium
  作者：Tatenda M. Mareya、Tracey M. Coady、Catherine O'Reilly、Michael Kinsella、Lee Coffey、Claire M. Lennon

  DOI：10.1002/open.202000088

  日期：2020.4

  enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo‐aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β‐aminonitriles, structural analogues of β‐hydroxynitriles was also investigated

  在具有底物3-羟基丁腈的腈水解红球菌SET1的腈水解反应中，完成了一系列全面的优化研究，包括pH，溶剂和温度。这些确定的温度为25°C，pH为7是保留对映选择性和活性的最佳条件。还确定了向有机转化混合物中添加有机溶剂的效果。研究结果表明，SET1仅适用于特定比例的所选有机水性介质。带有未保护和受保护的β-氨基腈（β的结构类似物）的分离物的官能团耐受性羟基腈的分离收率和选择性也很差，令人失望。分离物进一步用产生极佳收率和ee（> 99％（S）–异构体，收率50％）的α-氨基腈苯基甘氨腈生成酸进行评估。用该底物进行的一系列pH研究表明，pH 7是避免产物和底物降解的最佳p​​H。
• Enhanced enantioselectivity of an enzymatic reaction by the sulfur functional group. A simple preparation of optically active .beta.-hydroxy nitriles using a lipase
  作者：Toshiyuki Itoh、Yumiko Takagi、Shigenori Nishiyama

  DOI：10.1021/jo00004a033

  日期：1991.2

  The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the beta-(phenylthio)- or beta-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of beta-hydroxy nitriles using lipase P (Pseudomonas sp.).
• Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
  作者：Toshiyuki Itoh、Koichi Mitsukura、Wipa Kanphai、Yumiko Takagi、Hiroshi Kihara、Hiroshi Tsukube

  DOI：10.1021/jo971288m

  日期：1997.12.1

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.
• Itoh, Toshiyuki; Takagi, Yumiko, Chemistry Letters, 1989, p. 1505 - 1506
  作者：Itoh, Toshiyuki、Takagi, Yumiko

  DOI：——

  日期：——
• Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis by addition of a crown ether
  作者：Toshiyuki Itoh、Yuji Hiyama、Akio Betchaku、Hiroshi Tsukube

  DOI：10.1016/s0040-4039(00)77639-8

  日期：1993.4

  Both reaction rate and enantioselectivity in a lipase-catalyzed hydrolysis of beta-acetoxybutyronitrile were significantly enhanced by addition of hydroxymethyl-12-crown-4.