2--3-hydroxy-propanal | 132881-74-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2--3-hydroxy-propanal
• 英文别名: 2-(N-Acetylamino)-3-hydroxy-propanal；N-(1-hydroxy-3-oxopropan-2-yl)acetamide
• CAS: 132881-74-4
• 化学式: C₅H₉NO₃
• mdl: MFCD19217872
• 分子量: 131.131
• InChiKey: UCDYZMSOUKWOIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2--3-hydroxy-propanal 在 盐酸 、 indium 、 臭氧 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (4S,5S)-5-Acetylamino-2,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Indium-Mediated Stereoselective Synthesis of Truncated, 6- and 7-Carbon Sialic Acids

  摘要：

  我们合成了几种 6 碳和 7 碳的硅酸衍生物，无需繁琐的保护基操作，而且总产率很高。合成的一个关键步骤是通过铟介导的 2-（溴甲基）丙烯酸乙酯加成法对合适的δ-氨基醛衍生物进行链延伸。 在酸性反应条件下，以高反式-立体选择性获得了相应的扩展烯酸盐。 臭氧分解以游离形式产生了所需的 4-酰氨基取代的己酮磺酸和庚酮磺酸，可用于生化研究。

  DOI：

  10.1055/s-2002-35564
• 作为产物：
  描述：

  N-acetyl-2-amino-4-phenyl-3-buten-1-ol 在 二甲基硫 、 臭氧 作用下， 生成 2--3-hydroxy-propanal
  参考文献：
  名称：

  .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine

  摘要：

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.

  DOI：

  10.1021/jo00012a015

文献信息

• Studies of 2-amino-2-deoxy-dl-glyceraldehyde. Identification of an n-acetyl derivative amongst the degradation products of the ovalbumin glycopeptide
  作者：S. David、A. Veyrieres

  DOI：10.1016/s0008-6215(00)81084-8

  日期：1969.5

  5 ) 2 ( 1 ). The product obtained on hydrolysis of 1 with concentrated hydrochloric acid is stable only in acid solution and behaves as a hydrate or a polymer of CH 2 OH·CH N + H 3 ·CHO Cl − . It affords a crystalline semicarbazone hydrochloride ( 2 ), 2,4-dinitrophenylhydrazonehydrochloride ( 3 ), and dithioacetal oxalate ( 4 ). Other acyl and alkyl derivatives have been prepared directly from compound

  摘要用氢化铝锂还原2-氨基-3,3-二乙氧基丙酸乙酯可得到缩醛CH 2 OH·CHNH 2·CH（OC 2 H 5）2（1）。用浓盐酸水解1得到的产物仅在酸性溶液中稳定，并表现为水合物或CH 2 OH·CH N + H 3·CHO Cl-的聚合物。得到结晶的半卡巴zone盐酸盐（2），2，4-二硝基苯hydr盐酸盐（3）和二硫缩醛草酸盐（4）。其他酰基和烷基衍生物已直接由化合物1制备。仅在溶液中鉴定出的醛CH 2 OH.CH（NHCOCH 3）.CHO应该在某些含有氨基糖的多糖进行Smith降解后形成。二乙缩醛12及其O-甲基衍生物15、2,4-二硝基苯基hydr 13，制备该醛的乙撑二硫缩醛14。巯基分解后，还从卵清蛋白糖肽的史密斯降解产物中分离了衍生物14。
• Veyrieres,A., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1965, vol. 260, p. 6135 - 6137
  作者：Veyrieres,A.

  DOI：——

  日期：——
• HUNG, REBECCA R.;STRAUB, JULIE ANN;WHITESIDES, GEORGE M., J. ORG. CHEM., 56,(1991) N2, C. 3849-3855
  作者：HUNG, REBECCA R.、STRAUB, JULIE ANN、WHITESIDES, GEORGE M.

  DOI：——

  日期：——
• .alpha.-Amino aldehyde equivalents as substrates for rabbit muscle aldolase: synthesis of 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
  作者：Rebecca R. Hung、Julie Ann Straub、George M. Whitesides

  DOI：10.1021/jo00012a015

  日期：1991.6

  This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.
• Indium-Mediated Stereoselective Synthesis of Truncated, 6- and 7-Carbon Sialic Acids
  作者：Wolf-Dieter Fessner、Mathias Warwel

  DOI：10.1055/s-2002-35564

  日期：——

  Several 6- and 7-carbon sialic acid derivatives were synthesized, without tedious protecting group manipulations, in high overall yields. A key step of the synthesis was the chain extension of suitable α-amino aldehyde derivatives by an indium-mediated addition of ethyl 2-(bromomethyl)acrylate. Under acidic reaction conditions, the corresponding extended enoates were obtained with high trans-stereoselectivity. Ozonolysis furnished the desired 4-acylamino-substituted hexulosonic and heptulosonic acids in free form for biochemical studies.

  我们合成了几种 6 碳和 7 碳的硅酸衍生物，无需繁琐的保护基操作，而且总产率很高。合成的一个关键步骤是通过铟介导的 2-（溴甲基）丙烯酸乙酯加成法对合适的δ-氨基醛衍生物进行链延伸。 在酸性反应条件下，以高反式-立体选择性获得了相应的扩展烯酸盐。 臭氧分解以游离形式产生了所需的 4-酰氨基取代的己酮磺酸和庚酮磺酸，可用于生化研究。