3-氨基-n-[(9h-芴-9-基甲氧基)羰基]-d-丙氨酸盐酸盐 | 487027-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 3-氨基-n-[(9h-芴-9-基甲氧基)羰基]-d-丙氨酸盐酸盐
• 中文别名: 氨基-n-[(9h-芴-9-基甲氧基)羰基]-d-丙氨酸盐酸盐；3-氨基-N-[芴甲氧羰基]-D-丙氨酸单盐酸盐
• 英文名称: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-aminopropanoic acid hydrochloride
• 英文别名: (2R)-3-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;hydrochloride
• CAS: 487027-89-4
• 化学式: C₁₈H₁₈N₂O₄*ClH
• 分子量: 362.813
• InChiKey: GJIUYXQXIOYBMD-PKLMIRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  3-氨基-n-[(9h-芴-9-基甲氧基)羰基]-d-丙氨酸盐酸盐 在 甲醇 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-nitro-benzenesulfonylamino)-propionic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the Fukuyama−Mitsunobu Reaction

  摘要：

  An efficient solid-phase synthetic route is described for the preparation of 13-membered amine-bridged cyclic enkephalin analogues (ABEs) 1a and 1c-1j (Figure 1) resulting from a sulfonamide-containing peptide whose backbone is bound to a resin. The Fukuyama-Mitsunobu reaction of the 2-nitrobenzenesulfonyl-protected amine bound to the solid support with protected aminoethanol in the presence of triphenylphosphine and diisopropyl azodicarboxylate (DIAD) is utilized to prepare a resin-bound sulfonamide-protected secondary amine. After peptide cyclization, this protected amine functionality becomes the "amine bridge" of the target molecule. In addition, the reagent DIAD was found to be a superior reagent compared to diethyl azodicarboxylate (DEAD) in the solid-phase Fukuyama-Mitsunobu reaction.

  DOI：

  10.1021/jo020447l
• 作为产物：
  描述：

  Fmoc-D-天冬酰胺 在 吡啶 、 [双(三氟乙酰氧基)碘]苯 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以89%的产率得到3-氨基-n-[(9h-芴-9-基甲氧基)羰基]-d-丙氨酸盐酸盐
  参考文献：
  名称：

  Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the Fukuyama−Mitsunobu Reaction

  摘要：

  An efficient solid-phase synthetic route is described for the preparation of 13-membered amine-bridged cyclic enkephalin analogues (ABEs) 1a and 1c-1j (Figure 1) resulting from a sulfonamide-containing peptide whose backbone is bound to a resin. The Fukuyama-Mitsunobu reaction of the 2-nitrobenzenesulfonyl-protected amine bound to the solid support with protected aminoethanol in the presence of triphenylphosphine and diisopropyl azodicarboxylate (DIAD) is utilized to prepare a resin-bound sulfonamide-protected secondary amine. After peptide cyclization, this protected amine functionality becomes the "amine bridge" of the target molecule. In addition, the reagent DIAD was found to be a superior reagent compared to diethyl azodicarboxylate (DEAD) in the solid-phase Fukuyama-Mitsunobu reaction.

  DOI：

  10.1021/jo020447l

文献信息

• Solid-Phase Synthesis of Amine-Bridged Cyclic Enkephalin Analogues via On-Resin Cyclization Utilizing the Fukuyama−Mitsunobu Reaction
  作者：Yosup Rew、Murray Goodman

  DOI：10.1021/jo020447l

  日期：2002.12.1

  An efficient solid-phase synthetic route is described for the preparation of 13-membered amine-bridged cyclic enkephalin analogues (ABEs) 1a and 1c-1j (Figure 1) resulting from a sulfonamide-containing peptide whose backbone is bound to a resin. The Fukuyama-Mitsunobu reaction of the 2-nitrobenzenesulfonyl-protected amine bound to the solid support with protected aminoethanol in the presence of triphenylphosphine and diisopropyl azodicarboxylate (DIAD) is utilized to prepare a resin-bound sulfonamide-protected secondary amine. After peptide cyclization, this protected amine functionality becomes the "amine bridge" of the target molecule. In addition, the reagent DIAD was found to be a superior reagent compared to diethyl azodicarboxylate (DEAD) in the solid-phase Fukuyama-Mitsunobu reaction.