(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-3-benzo[1,3]dioxol-5-yl-1-(3-carboxymethoxy-phenyl)-propyl ester | 178446-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-3-benzo[1,3]dioxol-5-yl-1-(3-carboxymethoxy-phenyl)-propyl ester
• 英文别名: 2-[3-[(1R)-3-(1,3-benzodioxol-5-yl)-1-[(2S)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carbonyl]oxypropyl]phenoxy]acetic acid
• CAS: 178446-04-3
• 化学式: C₃₁H₃₇NO₉
• 分子量: 567.636
• InChiKey: HUIYWNWRANNCCJ-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙二胺 、 (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-3-benzo[1,3]dioxol-5-yl-1-(3-carboxymethoxy-phenyl)-propyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以27%的产率得到[(1R)-3-(1,3-benzodioxol-5-yl)-1-[3-[2-[2-[[2-[3-[(1R)-3-(1,3-benzodioxol-5-yl)-1-[(2S)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carbonyl]oxypropyl]phenoxy]acetyl]amino]ethylamino]-2-oxoethoxy]phenyl]propyl] (2S)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis and activity of bivalent FKBP12 ligands for the regulated dimerization of proteins

  摘要：

  The total synthesis and in vitro activities of a series of chemical inducers of dimerization (CIDs) is described. The use of small-molecule CIDs to control the dimerization of engineered FKBP12-containing fusion proteins has been demonstrated to have broad utility in biological research as well as potential medical applications in gene and cell therapies. The facility and flexibility of preparation make this new class of wholly synthetic compounds exceptionally versatile tools for the study of intracellular signaling events mediated by protein-protein interactions or protein localization. While some congeners possess potency comparable to or better than the first generation natural product-derived CID, FK1012, structure-activity relationships are complex and underscore the need for application-specific compound optimizations. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00125-4
• 作为产物：
  描述：

  3-羟基苯乙酮 在 Lindlar's catalyst 4-二甲氨基吡啶 、 氢氧化钾 、 氢气 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -20.0~20.0 ℃ 、344.74 kPa 条件下， 反应 28.25h， 生成 (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-3-benzo[1,3]dioxol-5-yl-1-(3-carboxymethoxy-phenyl)-propyl ester
  参考文献：
  名称：

  Synthesis and activity of bivalent FKBP12 ligands for the regulated dimerization of proteins

  摘要：

  The total synthesis and in vitro activities of a series of chemical inducers of dimerization (CIDs) is described. The use of small-molecule CIDs to control the dimerization of engineered FKBP12-containing fusion proteins has been demonstrated to have broad utility in biological research as well as potential medical applications in gene and cell therapies. The facility and flexibility of preparation make this new class of wholly synthetic compounds exceptionally versatile tools for the study of intracellular signaling events mediated by protein-protein interactions or protein localization. While some congeners possess potency comparable to or better than the first generation natural product-derived CID, FK1012, structure-activity relationships are complex and underscore the need for application-specific compound optimizations. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00125-4