ethyl 2-(hydroxyimino)-3-phenylpropanoate | 6943-96-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(hydroxyimino)-3-phenylpropanoate
• 英文别名: ethyl 2-hydroxyimino-3-phenylpropionate；ethyl benzylglyoxylate oxime；2-hydroxyimino-3-phenyl-propionic acid ethyl ester；2-Hydroxyimino-3-phenyl-propionsaeure-aethylester；Phenylbrenztraubensaeure-aethylester-oxim；α-Oximino-β-phenyl-propionsaeure-aethylester；Ethyl 2-hydroxyimino-3-phenylpropanoate
• CAS: 6943-96-0；70564-52-2；70564-53-3
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: QGTGTZUULIEJAP-UHFFFAOYSA-N

物化性质

• 沸点：
  347.9±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(hydroxyimino)-3-phenylpropanoate 在 sodium tetrahydroborate 、 水 、 镍 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以83%的产率得到DL-苯丙氨酸
  参考文献：
  名称：

  使用硼氢化钠和无定形镍催化剂可增强C–N多键的还原†

  摘要：

  非晶态镍粉（Ni 0）在温和的水性碱性条件下用作催化剂，以增强硼氢化钠介导的C–N多键的还原，如肟，亚胺，azo和腈，从而生成相应的胺。优异的产量。

  DOI：

  10.1039/c1ob06471a
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 亚硝酸乙酯 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到ethyl 2-(hydroxyimino)-3-phenylpropanoate
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone esters

  摘要：

  The extracts of Inula britannica have anti-inflammatory, anti-bacterial, anti-hepatitic, and anti-tumor activities. Various sesquiterpene lactones with cytotoxic properties including 1-O-acetylbritannilactone (1) have been isolated from this Chinese medicinal plant. Eight derivatives of 1-O-acetylbritannilactone, (2-O-alkyloxime-3-phenyl)-propionyt-1-O-acetylbritannilactone esters were designed and synthesized. Four of these compounds were tested to show inhibitory activity on the growth of human leukemia HL-60 and cancer Bel-7402 cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.024

文献信息

• Convenient Method for Reduction of C-N Double Bonds in Oximes, Imines, and Hydrazones Using Sodium Borohydride–Raney Ni System
  作者：Yihua Yang、Shouxin Liu、Junzhang Li、Xia Tian、Xiaoli Zhen、Jianrong Han

  DOI：10.1080/00397911.2011.562063

  日期：2012.9

  Abstract A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. GRAPHICAL

  摘要 开发了一种在 Raney Ni 催化下用硼氢化钠还原肟、亚胺和腙中 CN 双键的实用方法。反应在碱性水溶液中进行，经过简单的程序，以中等收率得到所需产物。该方法可用于合成更简单的脂肪族或芳香族胺及其类似物。图形概要
• Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
  作者：Eloi P Coutant、Vincent Hervin、Glwadys Gagnot、Candice Ford、Racha Baatallah、Yves L Janin

  DOI：10.3762/bjoc.14.264

  日期：——

  We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered

  我们在这里探索了基于古老的丙二酸二乙酯对α-氨基酯的接触范围，该方法涉及丙二酸二乙酯在醛上的Knoevenagel缩合反应，所得亚烷基丙二酸酯的还原，相应α-羟基亚氨基酯的制备及其最终还原。尽管遇到了一些意想不到的限制，但这种合成途径被证明是通用的。在进行肟化步骤之前，使用Suzuki-Miyaura偶联或环加成法对某些中间体进行了合成修饰，从而获得了更多的α-氨基酯。此外，探索了其他通往α-羟基亚氨基酯的途径，包括试图改善乙基β-溴-α-羟基亚氨基羧酸酯与各种烷基呋喃化合物之间的环加成反应。
• Synthesis and activity evaluation of the cyclic dipeptides arylidene N -alkoxydiketopiperazines
  作者：Xia Tian、Juan Feng、Shi-ming Fan、Xiao-li zhen、Jian-rong Han、Shou-xin Liu

  DOI：10.1016/j.bmc.2016.08.038

  日期：2016.11

  intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the rearrangement mechanism. Most compounds exhibited antitumor activity. Several compounds were more potent against caspase-3. Specifically, compounds 6e, 6g, and 6f inhibited caspase-3 at IC50 values lying within the

  设计了一系列芳基N-烷氧基二酮哌嗪并通过肟醚形成和分子内酰化立体合成。讨论了可能的环化和酸催化的重排-断裂机理。新型二酮哌嗪的晶体结构进一步证实了重排机理。大多数化合物表现出抗肿瘤活性。几种化合物对caspase-3更有效。具体而言，化合物6e，6g和6f在IC 50上抑制caspase-3值在低微摩尔范围内，并显示出良好的选择性。基于分子对接的结果，还讨论了烷氧基二酮哌嗪在caspase-3活性中心的结合方式。
• Nano-K₂CO₃: preparation, characterization and evaluation of reactive activities
  作者：Jun-Zhang Li、Shi-Ming Fan、Xuan-Fei Sun、Shouxin Liu

  DOI：10.1039/c5ra21597h

  日期：——

  Nano-K₂CO₃ shows higher basicity and can replace sodium (potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds.

  Nano-K2CO3显示出更高的碱性，并且可以替代钠（钾）烷氧化物来进行活性亚甲基化合物的单烷基化和氧化反应。
• New, Convenient Methods of Synthesis and Resolution of 1,2-Amino Alcohols
  作者：Mariappan Periasamy、Sangarappan Sivakumar、Meda Narsi Reddy

  DOI：10.1055/s-2003-41046

  日期：——

  Oximes of α-keto esters are reduced to obtain the corresponding amino alcohols using NaBH4 in combination with I2, CH3COOH, TiCl4, ZrCl4, COCl2, H2SO4, and TMS-Cl in 60-85% yields. The racemic phenylglycinol, phenylalaninol, and 2-aminobutanol are resolved using dibenzoyl-l-tartaric acid to obtain enantio­meric samples of >98% ee.

  使用 NaBH4 与 I2、CH3COOH、TiCl4、ZrCl4、COCl2、H2SO4 和 TMS-Cl 结合使用，δ-酮酯的肟被还原，得到相应的氨基醇，收率为 60-85%。使用二苯甲酰基酒石酸分解外消旋苯基甘氨醇、苯基丙氨醇和 2- 氨基丁醇，可获得对映体样品，ee >98%。