3-cyclopropyl-2,2-dihydroxy-3-oxo-propionic acid ethyl ester | 85297-89-8

• 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: 3-cyclopropyl-2,2-dihydroxy-3-oxo-propionic acid ethyl ester
• 英文别名: 3-cyclopropyl-2,3-dioxopropionate；ethyl 3-cyclopropyl-2,2-dihydroxy-3-oxopropanoate
• CAS: 85297-89-8
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: UDFWZFYDQIYNMK-UHFFFAOYSA-N

物化性质

• 沸点：
  296.2±35.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyclopropyl-2,2-dihydroxy-3-oxo-propionic acid ethyl ester 生成 乙醛酸乙酯
  参考文献：
  名称：

  GOWAL, H.;DAO, LE, H.;DAHN, H., HELV. CHIM. ACTA, 1985, 68, N 1, 173-180

  摘要：

  DOI：
• 作为产物：
  描述：

  3-cyclopropyl-3-oxo-2-(triphenylphosphanylidene)-propionic acid ethyl ester 在 potassium peroxomonosulphate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 以71.2%的产率得到3-cyclopropyl-2,2-dihydroxy-3-oxo-propionic acid ethyl ester
  参考文献：
  名称：

  Syntheses of isotopically labelled angiotensin II receptor antagonist GR138950X

  摘要：

  Syntheses of [C-13] and [C-14]-labelled versions of angiotensin II receptor antagonist GR138950X, labelled in the imidazole carboxamide residue, are described. These involved preparation of an iodoimidazole substrate by a novel iododecarboxylation procedure, followed by cyanation with a mixture of carbon-labelled potassium cyanide and copper (I) iodide in DMF at high temperature. The preparation of a mass-labelled (M+5) version of GR138950X is also described. This involved the synthesis of an [C-13(3), N-15(2)]-labelled imidazole from a 1,2,3-tricarbonyl compound, C-13(3)]propionaldehyde and [N-15]ammonia. The labelled imidazole was further elaborated into multiply-labelled GR138950X.

  DOI：

  10.1002/(sici)1099-1344(199605)38:5<453::aid-jlcr852>3.0.co;2-#

文献信息

• Nucleophilic 1,2-Shifts of Alkoxycarbonyl and Carboxylate Groups in the Benzilic-Acid Type Rearrangement of ?,?-Dioxobutyric Esters
  作者：Heike Gowal、L� H. Dao、Hans Dahn

  DOI：10.1002/hlca.19850680121

  日期：1985.2.13

  high pH, the benzilic-acid rearrangement with exclusive 1,2-shift of the COO(t-Bu) group; the same is true for the corresponding isopropyl ester 1c and ethyl ester 1b at high pH, whereas at lower pH, the overall picture of these reactions is complicated by concurrent hydrolysis of the ester, followed by a 1,2-shift of the COO− group. Consequently, the shift of these electron-attracting groups cannot be

  α，β-二氧代丁酸叔丁酯（水合物；1d）在中等或高pH条件下会发生苯甲酸重排，COO（t -Bu）基团仅发生1,2-移位；相同的是真正的对应的异丙基酯1C和乙酯1B在高pH值，而在较低的pH值，这些反应的整体图像，通过酯的水解并发，随后的1,2-移复杂COO -团体。因此，不能认为这些吸电子基团的转移是系统地不利的（例如，与烷基转移相比）。重排的动力学测量结果显示了两种酯（以及类似的乙酯图1b，并且还用于乙基3-环丙基α，β-dioxopropionate（4））的特性速率曲线：在相对低的pH，ķ成正比[HO - ]，接近饱和的增加[HO - ]（解释为完整将衬底传入水合物单价阴离子），这是由另一速率增加，接着在较高的pH的变换ķ成正比[HO - ]（可能是由于二价阴离子水合物的反应）。1b-d的k值相似性表明，在COOR移动中，由R引起的位阻可忽略不计。
• [EN] SULPHUR-LINKED IMIDAZOLE COMPOUNDS FOR THE TREAMENT OF HIV<br/>[FR] COMPOSES D'IMIDAZOLE A LIAISON SOUPHRE POUR LE TRAITEMENT DU VIH
  申请人：PFIZER LTD

  公开号：WO2005100322A1

  公开（公告）日：2005-10-27

  This invention relates to isophthalonitrile derivatives of formula (I) or pharmaceutically acceptable salts, solvates or derivative thereof, wherein R1 to R3 are defined in the description, and to processes for the preparation thereof, intermediates used in their preparation of, compositions containing them and the uses of such derivatives.The compounds of the present invention bind to the enzyme reverse transcriptase and are modulators, especially inhibitors thereof.

  本发明涉及具有以下结构的异苯二甲腈衍生物（I）或药学上可接受的盐、溶剂或其衍生物，其中R1至R3在说明中有定义，并涉及其制备方法、制备中使用的中间体、含有它们的组合物以及这些衍生物的用途。本发明的化合物与酶逆转录酶结合，并且是其调节剂，特别是抑制剂。
• Trifluoroacetic Acid Catalyzed Cascade Reactions of 2,3‐Diketoesters with Cyclohexane‐1,3‐diones: Strategy Towards 4‐Hydroxybenzofuran Derivatives
  作者：Qiang Sha、Haixuan Liu、Yuan Li

  DOI：10.1002/adsc.201900056

  日期：2019.4

  An efficient trifluoroacetic acid catalyzed cascade reaction of 2,3‐diketoesters with cyclohexane‐1,3‐diones is described for the synthesis of a series of 4‐hydroxybenzofurans. This simple protocol has the advantages of easy operation, readily available starting materials, good functional group tolerance, and easily scale‐up. Subsequent derivatization of the 4‐hydroxybenzofurans provides a reasonable

  描述了一种有效的三氟乙酸催化的2,3-二酮酸酯与环己烷-1,3-二酮的级联反应，用于合成一系列的4-羟基苯并呋喃。这种简单的协议具有易于操作，易于获得的起始原料，良好的官能团耐受性和易于放大的优点。随后对4-羟基苯并呋喃进行衍生化提供了一条获得高度官能化苯并呋喃的合理途径。
• Alkoxycarbonyl- and Carboxylate-Group Migrations in the Benzilic Acid Rearrangement of Ethyl Cyclopropane-2, 3-dioxopropionate
  作者：Hans Dahn、L� H. Dao、Rannoo Hunma

  DOI：10.1002/hlca.19820650813

  日期：1982.12.15

  medium C3H5COC (OH)2COOEt (1b) is transformed into C3H5C (OH)(COOH)2 (2a). Labelling experiments show that the cyclopropyl group is not shifted, but only ROOC and/or −O2C groups. GC./MS. and NMR. analysis after incomplete reaction show that both ROOC- and −O2C-groups Migrate; at higher pH (ca. 14) the ester group rearrangement seems to be more important than at pH ca.9-10.

  在碱性介质中，将C 3 H 5 COC（OH）2 COOEt（1b）转化为C 3 H 5 C（OH）（COOH）2（2a）。标记实验表明，环丙基不移动，而仅ROOC和/或- ö 2 C两组。GC./MS。和NMR。后反应不完全显示分析，这两个ROOC-和- ö 2 C-组迁移; 在较高的pH值（约14）下，酯基的重排似乎比在pH值约4时更为重要。9-10。
• Sulphur-Linked Imidazone Compounds for the Treatment of Hiv/Aids
  申请人：Jones Lyn Howard

  公开号：US20080132549A1

  公开（公告）日：2008-06-05

  This invention relates to isophthalonitrile derivatives of formula (I) or pharmaceutically acceptable salts, solvates or derivative thereof, wherein R 1 to R 3 are defined in the description, and to processes for the preparation thereof, intermediates used in their preparation of, compositions containing them and the uses of such derivatives. The compounds of the present invention bind to the enzyme reverse transcriptase and are modulators, especially inhibitors thereof.

  本发明涉及公式（I）的异苯二腈衍生物或其药学上可接受的盐、溶剂或衍生物，其中R1至R3在说明中定义，并涉及其制备过程、制备中使用的中间体、含有它们的组合物以及这种衍生物的用途。本发明的化合物与酶逆转录酶结合，并且是其调节剂，特别是抑制剂。