(S)-(+)-3-羟基丁腈 | 123689-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-(+)-3-羟基丁腈
• 中文别名: (S)-3-羟基丁腈
• 英文名称: 3-hydroxybutyronitrile
• 英文别名: (S)-3-Hydroxybutanenitrile；(3S)-3-hydroxybutanenitrile
• CAS: 123689-95-2
• 化学式: C₄H₇NO
• 分子量: 85.1057
• InChiKey: BYJAJQGCMSBKPB-BYPYZUCNSA-N

物化性质

• 沸点：
  217℃
• 密度：
  0.991
• 闪点：
  85℃

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

反应信息

• 作为反应物：
  描述：

  间苯三酚 、 (S)-(+)-3-羟基丁腈 在 盐酸 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 (S)-4-Imino-2-methyl-chroman-5,7-diol
  参考文献：
  名称：

  A concise synthesis of chiral 2-methyl chroman-4-ones : Stereo selective build-up of the chromanol moiety of anti-HIV agent calanolide A

  摘要：

  Inter- and Intramolecular Houben-Hoesch reactions have been used for the first time for the enantioselective synthesis of both the antipodes of 5,7-dimethoxy-2-methyl chroman-4-one. (R)-7-Methoxy-2-methyl chroman-4-one has been diastereoselectively elaborated to the dimethylchromanol moiety of calanolide A.

  DOI：

  10.1016/s0040-4039(00)73429-0
• 作为产物：
  描述：

  (+/-)-3-<(methylthio)acetoxy>butyronitrile 在 Lipase P 水 、 丙酮 作用下， 反应 3.0h， 生成 (S)-(+)-3-羟基丁腈 、 (3R)-3-羟基丁腈
  参考文献：
  名称：

  Itoh, Toshiyuki; Takagi, Yumiko, Chemistry Letters, 1989, p. 1505 - 1506

  摘要：

  DOI：

文献信息

• Diverse synthesis of the C ring fragment of bryostatins via Zn/Cu-promoted conjugate addition of α-hydroxy iodide with enone
  作者：Zhiwen Chu、Ruiqi Tong、Yufan Yang、Xuanyi Song、Tian bao Hu、Yu Fan、Chen Zhao、Lu Gao、Zhenlei Song

  DOI：10.1016/j.cclet.2020.11.039

  日期：2021.1

  precursors for constructing the C ring of bryostatins, has been developed via a Zn/Cu-promoted conjugate addition of α-hydroxy iodides with enones. The reaction leads to direct formation of the C21-C22 bond and tolerates diverse functionalities at the C17-, C18- and C24-positions. The approach also enables a more concise synthesis of the known C ring intermediate (10 longest linear steps and 14 total

  摘要通过锌/铜促进的α-羟基碘化物与烯酮的共轭加成，开发了一种收敛方法，即1,5-羟基酮，这是构建bryostatins C环的一般前体。该反应导致C21-C22键的直接形成，并容许在C17-，C18-和C24-位的多种官能度。该方法还可以更精确地合成已知的C环中间体（10个最长线性步骤和14个总步骤），而在我们的苔藓抑素8的总合成中，它以前的合成方法（17个最长线性步骤和22个总步骤）相反。
• Enhanced Enantioselectivity of the Lipase-Catalyzed Hydrolysis by the Addition of a Catalytic Amount of an Amino Alcohol
  作者：Toshiyuki Itoh、Eri Ohira、Yumiko Takagi、Shigenori Nishiyama、Kaoru Nakamura

  DOI：10.1246/bcsj.64.624

  日期：1991.2

  l-Methioninol (l-MetOH) was discovered to be an effective additive for improving the enantioselectivity of lipase-catalyzed hydrolysis. It was found that l-MetOH accelerated the enzyme-catalyzed hydrolysis of (R)-3-acetoxybutyronitrile (1) and inhibited that of (S)-1.

  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。
• 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.