(S)-N-benzyl-2-hydroxypropionamide | 103808-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-benzyl-2-hydroxypropionamide
• 英文别名: (S)-N-benzyl-2-hydroxypropanamide；(S)-N-Benzyl-2-hydroxypropanamid；(S)-1-benzylcarbamoyl-ethanol；N-benzyl-2-hydroxypropanamide；(S)-N-benzyl lactamide；2(S)-hydroxypropionic acid benzylamide；(2S)-N-benzyl-2-hydroxypropanamide
• CAS: 103808-45-3
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: SYZQHWOGYNEXNG-QMMMGPOBSA-N

物化性质

• 沸点：
  393.7±35.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyl-2-hydroxypropionamide 在 lithium aluminium tetrahydride 作用下， 生成 (2S)-1-[benzyl(prop-2-enyl)amino]propan-2-ol
  参考文献：
  名称：

  Stereochemistry and regiochemistry of heteroatom directed reactions. Part 4. Palladium(II)-catalyzed synthesis of optically active tetrahydro-1,4-oxazine derivatives

  摘要：

  Three different types of morpholine derivatives 1-3 could be obtained from allylic amine substrates 4 in high yield and excellent diastereoselectivity by slight, variation of the Pd(II)-Cu(II) reagents system.

  DOI：

  10.1021/jo00070a001
• 作为产物：
  描述：

  L(-)-乳酸乙酯 、 苄胺 以74%的产率得到(S)-N-benzyl-2-hydroxypropionamide
  参考文献：
  名称：

  一种使用[1,2-环氨基磺酸]不对称合成烷基取代的哌啶-2-酮的[3 + 3]环化策略：从L-正缬氨酸正式合成（S）-甜菜碱

  摘要：

  一组代表性的1,2-环氨基磺酸盐与原丙酸三乙酯的区域选择性开环反应在酸性水解后有效地进行，以递送相应的δ-氨基-α，β-不饱和酯。不饱和酯的氢化和随后的热环化提供了相关的烷基取代的哌啶-2-酮。这种方法代表了一种新的[3 + 3]环化策略，用于烷基取代的哌啶-2-酮的不对称合成。由1-正缬氨酸的形式不对称合成（S）-丝氨酸说明了环化过程的效率。

  DOI：

  10.1016/j.tet.2012.09.081

文献信息

• Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral
  作者：Tomas Gustafsson、Fritiof Pontén、Peter H. Seeberger

  DOI：10.1039/b719603b

  日期：——

  A safe, functional-group-tolerant and high-throughput version of the trimethylaluminium mediated amide bond formation reaction has been developed in a microreactor system; rimonabant and efaproxiral were prepared to illustrate the utility of the method.

  在微反应器系统中，开发了一种安全、官能团耐受性强且高通量的三甲基铝介导的酰胺键形成反应版本；以利莫那班和依法罗西拉为例，展示了该方法的应用效果。
• FORUMLATIONS
  申请人：Bell Gordon Alastair

  公开号：US20090227453A1

  公开（公告）日：2009-09-10

  This invention relates to the use of lactamide compounds of formula (I): CH 3 CH(OH)C(═O)NR 1 R 2 , where R 1 and R 2 are each independently hydrogen; or C 1-6 alkyl, C 2-6 alkenyl or C 3-6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C 1-5 alkoxy, morpholinyl and NR 3 R 4 where R 3 and R 4 are each independently C 1-3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C 1-3 alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C 1-3 alkyl, in formulations to reduce the toxicity associated with other formulation components; to the use of certain lactamide compounds as solvents, especially in formulations, particularly in agrochemical formulations and in environmentally friendly formulations; to novel lactamide compounds; and to processes for preparing lactamide compounds.

  这项发明涉及使用式（I）的乳酰胺化合物：CH3CH(OH)C(═O)NR1R2，其中R1和R2分别独立地是氢；或C1-6烷基，C2-6烯基或C3-6环烷基，每种基团可选择地被最多三个取代基取代，这些取代基独立地选自苯基、羟基、C1-5烷氧基、吗啉基和NR3R4，其中R3和R4分别独立地是C1-3烷基；或苯基可选择地被最多三个取代基取代，这些取代基独立地选自C1-3烷基；或R1和R2与它们连接的氮原子一起形成吗啉基、吡咯啉基、哌啶基或氮杂环庚基环，每种环可选择地被最多三个取代基取代，这些取代基独立地选自C1-3烷基，在配方中减少与其他配方成分相关的毒性；使用某些乳酰胺化合物作为溶剂，特别是在配方中，尤其是在农药配方和环保配方中；新型乳酰胺化合物；以及制备乳酰胺化合物的方法。
• Catalytic Asymmetric Transfer Hydrogenation of Ketones Using [Ru(p-cymene)Cl2]2 with Chiral Amino Alcohol Ligands
  作者：Sudhindra H. Deshpande、Ashutosh A. Kelkar、Rajesh G. Gonnade、Savita K. Shingote、Raghunath V. Chaudhari

  DOI：10.1007/s10562-010-0408-y

  日期：2010.9

  Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(−)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60–90%) and moderate to good enantioselectivities (40–86%).Graphical AbstractAsymmetric transfer hydrogenation

  已经使用 [Ru(p-cymene)Cl2]2 和由 (S)-(-)-乳酸和扁桃酸合成的 β-氨基醇的新衍生物作为配体研究了芳族烷基酮的催化不对称转移氢化。获得了具有良好至优异转化率 (60–90%) 和中等至良好对映选择性 (40–86%) 的手性仲醇。图文摘要使用 [Ru(p-cymene)Cl2]2 和 β 研究了酮的不对称转移氢化-氨基醇由(S)-(-)-乳酸和扁桃酸作为配体合成。获得了具有良好至优异转化率（60-90%）和中等至良好对映选择性（40-86%）的手性仲醇。
• Amidation of unactivated ester derivatives mediated by trifluoroethanol
  作者：Christopher G. McPherson、Nicola Caldwell、Craig Jamieson、Iain Simpson、Allan J. B. Watson

  DOI：10.1039/c7ob00593h

  日期：——

  A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity

  已经开发了由2,2,2-三氟乙醇介导的催化酰胺化方案，可促进未活化的酯和胺的缩合，同时提供仲酰胺和叔酰胺。描述了该方法的完整范围和局限性，以及具有挑战性的底物（如无环仲胺和手性酯）的修饰条件，并保留了手性完整性。
• Modular Evolution of a Chiral Auxiliary for the 1,3-Dipolar Cycloaddition of Isomünchnones with Vinyl Ethers
  作者：Sergey N. Savinov、David J. Austin

  DOI：10.1021/ol017263y

  日期：2002.5.1

  [reaction: see text]. The 1,3-dipolar cycloaddition reaction has long been recognized as a powerful methodology in organic synthesis. More recently, this reaction has become a popular manifold for the construction of chemical diversity. Herein, we report the development of a chiral template for the facially selective cycloaddition of isomünchnones, a common class of 1,3-dipoles. The modular format

  [反应：请参见文字]。1，3-偶极环加成反应早已被认为是有机合成中的一种有效方法。最近，该反应已成为构建化学多样性的流行方法。在此，我们报告了异丁烯酮（一种常见的1,3-偶极类）的面部选择性环加成手性模板的开发。不对称单元的模块化形式允许选择性的系统优化。另外，通过异常容易的酯氨解除去了手性助剂。