(1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol | 220623-17-6

• 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: (1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol
• 英文别名: ((1S,2S,5R,6R)-6-(aminomethyl)-3-benzyl-3-azabicyclo[3.1.0]hexan-2-yl)methanol；[(1S,2S,5R,6R)-6-(aminomethyl)-3-benzyl-3-azabicyclo[3.1.0]hexan-2-yl]methanol
• CAS: 220623-17-6
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: QICFZDNCTMSTEP-SYQHCUMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol 在 sodium dihydrogenphosphate 、 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0~35.0 ℃ 、1.38 MPa 条件下， 反应 45.0h， 生成 (1S,2S,5R,6R)-3-aza-3-[(tert-butyl)oxycarbonyl]-6-(N-(9-fluorenylmethoxycarbonyl)aminomethyl)bicyclo[3.1.0]hexane-2-carboxylic acid
  参考文献：
  名称：

  Solid-Phase Guanidinylation as a Diversification Strategy of Poly-l-proline Type II Peptide Mimic Scaffolds

  摘要：

  [GRAPHICS]Solid phase guanidinylation of praline templated amino acids is studied as a diversification strategy of poly-L-proline type tl scaffolds.

  DOI：

  10.1021/ol0069711
• 作为产物：
  描述：

  (1R,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 methylsulfinylcarbanion 、 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 56.0h， 生成 (1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol
  参考文献：
  名称：

  Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents

  摘要：

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

  DOI：

  10.1021/jo9816109

文献信息

• WO2020150372A5
  申请人：——

  公开号：WO2020150372A5

  公开（公告）日：2023-01-26
• Strategies for the Solid-Phase Diversification of Poly-<scp>l</scp>-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation
  作者：Stevenson Flemer、Alexander Wurthmann、Ahmed Mamai、José S. Madalengoitia

  DOI：10.1021/jo8012258

  日期：2008.10.3

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.
• Solid-Phase Guanidinylation as a Diversification Strategy of Poly-<scp>l</scp>-proline Type II Peptide Mimic Scaffolds
  作者：Ahmed Mamai、Jose S. Madalengoitia

  DOI：10.1021/ol0069711

  日期：2001.2.1

  [GRAPHICS]Solid phase guanidinylation of praline templated amino acids is studied as a diversification strategy of poly-L-proline type tl scaffolds.
• Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents
  作者：Rui Zhang、Ahmed Mamai、Jose S. Madalengoitia

  DOI：10.1021/jo9816109

  日期：1999.1.1

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.