Tert-butyl (3S)-3-(acetylthio)piperidine-1-carboxylate | 610286-35-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: Tert-butyl (3S)-3-(acetylthio)piperidine-1-carboxylate
• 英文别名: tert-butyl (3S)-3-acetylsulfanylpiperidine-1-carboxylate
• CAS: 610286-35-6
• 化学式: C₁₂H₂₁NO₃S
• 分子量: 259.37
• InChiKey: LGDAYHSPCJKPMY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl (3S)-3-(acetylthio)piperidine-1-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 (S)-3-sulfanylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors

  摘要：

  Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S,4S)-4-mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity pro. le of these inhibitors. A Chloro substituent at the 2-position of 1a, compound 1d, retained potency against DNMT1, while N-6 alkylation, compound 7a, conserved DNMT3b2 activity. The concomitant substitutions of 1a at both 2- and N-6 positions reduced activity against both enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.132
• 作为产物：
  描述：

  (R)-1-N-Boc-3-甲烷磺酰氧基哌啶 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Tert-butyl (3S)-3-(acetylthio)piperidine-1-carboxylate
  参考文献：
  名称：

  Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors

  摘要：

  Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S,4S)-4-mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity pro. le of these inhibitors. A Chloro substituent at the 2-position of 1a, compound 1d, retained potency against DNMT1, while N-6 alkylation, compound 7a, conserved DNMT3b2 activity. The concomitant substitutions of 1a at both 2- and N-6 positions reduced activity against both enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.132

文献信息

• Process for the preparation of pleuromutilins
  申请人：Nabriva Therapeutics Forschungs GmbH

  公开号：EP1908750A1

  公开（公告）日：2008-04-09

  A process for the preparation of 14-O-[(N-(3-methyl-2-amino-butyryl-piperidinyl)sulfanyl) acetyl]mutilins of formula feasible for large-scale production of high purity products, and wherein the carbon atom at the piperidine ring attached to the sulphur atom is either in the (S)-configuration or in the (R)-configuration, and a new crystalline form of 14-O-[(N-3-methyl-2-(R)-amino-butyryl-piperidine-3(S)-yl)sulfanyl)acetyl]mutilin - hydrochloride.

  一种用于制备14-O-[(N-(3-甲基-2-氨基丁酰基哌啶基)硫基)乙酰]多黏菌素的工艺，适用于大规模生产高纯度产品，其中连接到硫原子的哌啶环上的碳原子处于(S)-构型或(R)-构型中的一种，以及一种新的14-O-[(N-3-甲基-2-(R)-氨基丁酰基哌啶-3(S)-基)硫基)乙酰]多黏菌素盐酸盐的结晶形式。
• PROCESS FOR THE PREPARATION OF PLEUROMUTILINS
  申请人：Macher Ingolf

  公开号：US20090253748A1

  公开（公告）日：2009-10-08

  A process for the preparation of 14-O-[(N-(3-methyl-2-amino-butyryl-piperidinyl)sulfanyl) acetyl]mutilins of formula (I) feasible for large-scale production of high purity products, and wherein the carbon atom at the piperidine ring attached to the sulphur atom is either in the (S)-configuration or in the (R)-configuration, and a new crystalline form of 14-O-[(N-3-methyl-2-(R)-amino-butyryl-piperidine-3(S)-yl)sulfanyl)acetyl]mutilin-hydrochloride.

  一种制备式（I）14-O-[(N-(3-甲基-2-氨基丁酰基-哌啶基)硫醇基乙酰基]黏菌素的工艺，适用于大规模生产高纯度产品，其中连接到硫原子的哌啶环上的碳原子处于（S）构型或（R）构型，并且一种新的14-O-[(N-3-甲基-2-(R)-氨基丁酰基-哌啶-3（S）-基硫醇基乙酰基]黏菌素盐酸盐的晶体形式。
• PLEUROMUTILINS AND PROCESS FOR THE PREPARATION OF PLEUROMUTILINS
  申请人：NABRIVA THERAPEUTICS AG

  公开号：US20130053571A1

  公开（公告）日：2013-02-28

  A process for the preparation of 14-O—[(N-(3-methyl-2-amino-butyryl-piperidinyl)sulfanyl)acetyl]mutilins of formula feasible for large-scale production of high purity products, and wherein the carbon atom at the piperidine ring attached to the sulphur atom is either in the (S)-configuration or in the (R)-configuration, and a new crystalline form of 14-O—[(N-3-methyl-2-(R)-amino-butyryl-piperidine-3(S)-yl)sulfanyl)acetyl]mutilin-hydrochloride.

  一种制备14-O-[(N-(3-甲基-2-氨基丁酰基-哌啶-3-基)硫酰基)乙酰基]木酮类化合物的方法，适用于大规模生产高纯度产品，其中连接到硫原子的哌啶环上的碳原子可以是(S)-构型或(R)-构型，并且一种新的14-O-[(N-3-甲基-2-(R)-氨基丁酰基-哌啶-3(S)-基)硫酰基]乙酰基木酮盐酸盐的晶型。
• US8334389B2
  申请人：——

  公开号：US8334389B2

  公开（公告）日：2012-12-18
• US8624033B2
  申请人：——

  公开号：US8624033B2

  公开（公告）日：2014-01-07