3-羟基-3-(吡啶-4-基)丙酸乙酯 | 591228-11-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 3-羟基-3-(吡啶-4-基)丙酸乙酯
• 英文名称: ethyl 3-hydroxy-3-(pyridin-4-yl)-propanoate
• 英文别名: 3-Hydroxy-3-(pyridin-4-yl)propionic acid ethyl ester；ethyl 3-hydroxy-3-pyridin-4-ylpropanoate
• CAS: 591228-11-4
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: GRIVNSOESQXSLB-UHFFFAOYSA-N

物化性质

• 沸点：
  339.3±27.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基-3-(吡啶-4-基)丙酸乙酯 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 叔丁基氯化镁 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 4-氨基-1-[5-O-[(2R,4S)-2-氧代-4-(4-吡啶基)-1,3,2-二氧磷杂环己烷-2-基]-BETA-D-呋喃阿拉伯糖基]-2(1H)-嘧啶酮
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Liver-Targeted Prodrug of Cytosine-1-β-d-arabinofuranoside Monophosphate for the Treatment of Hepatocellular Carcinoma

  摘要：

  Cytotoxic nucleosides have proven to be ineffective for the treatment of hepatocellular carcinoma (HCC) due, in part, to their inadequate conversion to their active nucleoside triphosphates (NTP) in the liver tumor and high conversion in other tissues. These characteristics lead to poor efficacy, high toxicity, and a drug class associated with an unacceptable therapeutic index. Cyclic 1-aryl-1,3-propanyl phosphate prodrugs selectively release the monophosphate of a nucleoside (NMP) into CYP3A4-expressing cells, such as hepatocytes, while leaving the prodrug intact in plasma and extrahepatic tissues. This prodrug strategy was applied to the monophosphate of the well-known cytotoxic nucleoside cytosine-1-beta-D-arabinofuranoside (cytarabine, araC). Compound 19S (MB07133), in mice, achieves good liver targeting compared to araC, generating > 19-fold higher cytarabine triphosphate (araCTP) levels in the liver than levels of araC in the plasma and > 12-fold higher araCTP levels in the liver than in the bone marrow, representing a > 120-fold and > 28-fold improvement, respectively, over araC administration.

  DOI：

  10.1021/jm0607449
• 作为产物：
  描述：

  异烟酰乙酸乙酯 在 乙醇 、 镍 作用下， 100.0 ℃ 、15.2 MPa 条件下， 生成 3-羟基-3-(吡啶-4-基)丙酸乙酯
  参考文献：
  名称：

  A Synthesis of 3-Alkylpiperidones

  摘要：

  DOI：

  10.1021/ja01252a068

文献信息

• Organic metal compound and process for preparing optically-active alcohols using the same
  申请人：Miki Takashi

  公开号：US20090062573A1

  公开（公告）日：2009-03-05

  The present invention provides an asymmetric reduction catalyst effective in preparing optically-active alcohol compounds having various functional groups, and a process for preparing optically-active alcohol compounds using said asymmetric reduction catalyst. The organic metal compound of the present invention is represented by the following general formula (1): wherein R 1 and R 2 may be mutually identical or different, and are an alkyl group, a phenyl group, a naphthyl group, a cycloalkyl group, or an alicyclic ring formed by binding R 1 and R 2 , which may have a substituent; R 3 is a hydrogen atom or an alkyl group; Cp is a cyclopentadienyl group, which may have a substituent, bound to M 1 via a π bond; X 1 is a halogen atom or a hydrido group; M 1 is rhodium or iridium; and * denotes asymmetric carbon.

  本发明提供了一种在制备具有各种官能团的光学活性醇化合物中有效的非对称还原催化剂，以及使用所述非对称还原催化剂制备光学活性醇化合物的方法。 本发明的有机金属化合物由以下通式(1)表示： 其中R1和R2可以相互相同或不同，并且是烷基、苯基、萘基、环烷基或由R1和R2结合形成的脂肪环环，其中可能含有取代基；R3是氢原子或烷基；Cp是环戊二烯基，可能含有取代基，通过π键与M1结合；X1是卤素原子或氢化物基团；M1是铑或铱；*表示不对称碳。
• 用于代谢性疾病治疗的化合物及其制备方法 和应用
  申请人：西安奥立泰医药科技有限公司

  公开号：CN109929005B

  公开（公告）日：2020-10-30

  本发明提供了一种用于代谢性疾病治疗的化合物，具有式(I)或式(Ⅱ)所示结构，或其消旋体，立体异构体，几何异构体，互变异构体，溶剂化物，水合物，代谢产物，药学上可接受的盐或其前药。本发明提供的化合物为FXR和/或TGR5受体激活物，其具有激活FXR和/或TGR5受体活性，可用于制备治疗慢性肝病、代谢性疾病或门脉高压症的药物。
• Process for reducing 3-heteroaryl-3-oxopropionic acid derivatives
  申请人：——

  公开号：US20030225274A1

  公开（公告）日：2003-12-04

  The present invention relates to a process for preparing stereoisomerically enriched 3-heteroaryl-3-hydroxycarboxylic esters by reducing 3-heteroaryl-3-oxocarboxylic esters in the presence of ruthenium-containing catalysts.

  本发明涉及一种在含有钌催化剂的情况下还原3-杂环基-3-酮羧酸酯以制备立体异构富集的3-杂环基-3-羟基羧酸酯的方法。
• Bu4N+-Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation
  作者：Donal O’Shea、Manas Das、Atul Manvar、Ian Fox、Dilwyn Roberts

  DOI：10.1055/s-0036-1588805

  日期：2017.11

  β-hydroxy esters, whereas employing catalytic Bu4NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated

  催化 Bu4NOAc 作为 2-（三甲基甲硅烷基）乙酸乙酯的硅活化剂，在 THF 中，用于合成 β-羟基酯，而使用催化 Bu4NOTMS 产生 α,β-不饱和酯。既定的反应条件适用于各种芳香族、杂芳香族、脂肪族醛和酮。反应是在室温下完成的，没有采取任何其他有机金属的专门预防措施。已经证明了通过甲硅烷基化 β-羟基酯随后消除形成 α,β-不饱和酯的逐步烯化途径。选择性产物形成的关键在于使用较弱的乙酸盐活化剂，它抑制随后的消除，而较强的 TMSO– 活化剂（和碱）促进添加和消除步骤。
• Cytarabine monophosphate prodrugs
  申请人：Metabasis Therapeutics, Inc.

  公开号：US07151092B2

  公开（公告）日：2006-12-19

  Compounds of Formula I, their preparation and uses are described: wherein: M and V are cis to one another and MH is cytarabine; the 5′ oxygen of said cytarabine is attached to the phosphorus; V is 4-pyridyl; and pharmaceutically acceptable prodrugs and salts thereof.

  本文描述了I式化合物的制备和用途：其中：M和V彼此顺式，MH是阿糖胞苷；所述阿糖胞苷的5'氧原子与磷相连；V为4-吡啶基；以及药学上可接受的前药和盐。