(S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl acetate | 144448-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl acetate
• 英文别名: tert-butyl (3S)-3-(acetyloxymethyl)piperidine-1-carboxylate
• CAS: 144448-01-1
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: DSKBLSVOGMOGAH-NSHDSACASA-N

物化性质

• 沸点：
  323.1±15.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl acetate 在 吡啶 、 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 (S)-piperidin-3-ylmethyl propionate
  参考文献：
  名称：

  N-[¹⁸F]Fluoroethylpiperidin-4ylmethyl Acetate, a Novel Lipophilic Acetylcholine Analogue for PET Measurement of Brain Acetylcholinesterase Activity

  摘要：

  The reduction of acetylcholinesterase (AChE) activity in the brain has been measured in dementia disorders such as Alzheimer's disease and dementia with Lewy bodies using C-11-labeled acetylcholine analogues, N-[C-11]methylpiperidin-4-yl acetate and propionate, and positron emission tomography (PET). Our aim was to develop an F-18-labeled acetylcholine analogue useful for brain AChE mapping with PET, since F-18, with a longer half-life, has advantages over C-11. In a preliminary study, a series of N-[C-14]ethylpiperidin-3-yl or -4yl-methanol esters (acetyl and propionyl esters) were newly designed and evaluated in vitro regarding the reactivity with and specificity to AChE using purified human enzymes, leading to a novel F-18-labeled acetylcholine analogue, N-[F-18]fluoroethylpiperidin-4-ylmethyl acetate. In rat experiments, the F-18-labeled candidate showed desirable properties for PET AChE measurement: high brain uptake of the authentic ester, high AChE specificity, a moderate hydrolysis rate, and low membrane permeability (metabolic trapping) of the metabolite.

  DOI：

  10.1021/jm049100w
• 作为产物：
  描述：

  乙酸乙烯酯 、 1-Boc-3-羟甲基哌啶 在 Lipase PS 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以42%的产率得到(S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl acetate
  参考文献：
  名称：

  N-[¹⁸F]Fluoroethylpiperidin-4ylmethyl Acetate, a Novel Lipophilic Acetylcholine Analogue for PET Measurement of Brain Acetylcholinesterase Activity

  摘要：

  The reduction of acetylcholinesterase (AChE) activity in the brain has been measured in dementia disorders such as Alzheimer's disease and dementia with Lewy bodies using C-11-labeled acetylcholine analogues, N-[C-11]methylpiperidin-4-yl acetate and propionate, and positron emission tomography (PET). Our aim was to develop an F-18-labeled acetylcholine analogue useful for brain AChE mapping with PET, since F-18, with a longer half-life, has advantages over C-11. In a preliminary study, a series of N-[C-14]ethylpiperidin-3-yl or -4yl-methanol esters (acetyl and propionyl esters) were newly designed and evaluated in vitro regarding the reactivity with and specificity to AChE using purified human enzymes, leading to a novel F-18-labeled acetylcholine analogue, N-[F-18]fluoroethylpiperidin-4-ylmethyl acetate. In rat experiments, the F-18-labeled candidate showed desirable properties for PET AChE measurement: high brain uptake of the authentic ester, high AChE specificity, a moderate hydrolysis rate, and low membrane permeability (metabolic trapping) of the metabolite.

  DOI：

  10.1021/jm049100w

文献信息

• N-[18F]fluoroethylpiperidin-4-ylmethyl butyrate: a novel radiotracer for quantifying brain butyrylcholinesterase activity by positron emission tomography
  作者：Tatsuya Kikuchi、Ming-Rong Zhang、Nobuo Ikota、Kiyoshi Fukushi、Toshimitsu Okamura、Kazutoshi Suzuki、Yasushi Arano、Toshiaki Irie

  DOI：10.1016/j.bmcl.2004.01.080

  日期：2004.4

  In Alzheimer's disease, cerebral cortical butyrylcholinesterase (BChE) activity is reported to be elevated. Our aim was to develop a novel F-18-labeled tracer for quantifying cerebral BChE activity by positron emission tomography. With in vitro screening of N-[C-14]ethylpiperidin-3- and 4-ylmethyl esters, N-[C-14]ethylpiperidin-4-ylmethyl butyrate was selected as a lead for F-18-labeling, affording N-[F-18]fluoroethylpiperidin-4-ylmethyl butyrate. The F-18-labeled butyrate showed the required properties for in vivo BChE measurement, that is, the lipophilic nature of the authentic ester, high specificity to B3ChE, a moderate hydrolysis rate, and the hydrophilic nature of the metabolite. (C) 2004 Elsevier Ltd. All rights reserved.
• CASITAS B-LINEAGE LYMPHOMA PROTOONCOGENE B (CBL-B) DEGRADING COMPOUNDS AND ASSOCIATED METHODS OF USE
  申请人：[en]ARVINAS OPERATIONS, INC.

  公开号：WO2024112692A1

  公开（公告）日：2024-05-30

  Provided herein are compounds of formula (I) and salts and compositions thereof which find utility as modulators of Cbl-b in the treatment of various forms of cancer.