methyl (1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylate | 474434-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylate
• 英文别名: (1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylic acid methyl ester；methyl (1'S,2'R,3'aS,6'aR)-2'-azido-5,5-dimethylspiro[1,3-dioxane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-1'-carboxylate
• CAS: 474434-30-5
• 化学式: C₁₅H₂₃N₃O₄
• 分子量: 309.365
• InChiKey: FQKSJTCIYOFWJD-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylate 在 palladium on activated charcoal lithium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 50.5h， 生成
  参考文献：
  名称：

  A Bicyclic Cispentacin Derivative as a Novel Reverse Turn Inducer in a GnRH Mimetic

  摘要：

  A cispentacin-derived bicyclic beta-amino acid (Bic) has been synthesized and incorporated into the 6-position of GnRH. The new GnRH analogue has been characterized with respect to its structure in solution and its activity and affinity toward the human GnRH receptor.

  DOI：

  10.1021/jo025857o
• 作为产物：
  描述：

  methyl (1'S,2'S,3'aS,6'aR)-2'-hydroxy-5,5-dimethylspiro[1,3-dioxane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-1'-carboxylate 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 methyl (1R,2S,3R,5S)-7,7-(2',2'-dimethyltrimethylenedioxy)-3-azidobicyclo[3.3.0]octane-2-carboxylate
  参考文献：
  名称：

  Synthesis and Conformational Analysis of a Novel Ansadipeptide

  摘要：

  以酪氨酸(5)和Bic 3b为氨基酸成分，草酸为连接键，合成了一种新型的Ansapeptide 6。 通过分子力学计算了6的构象性质。

  DOI：

  10.1055/s-2002-34378

文献信息

• Synthesis and Conformational Analysis of a Novel Ansadipeptide
  作者：Johann Mulzer、Oliver Langer

  DOI：10.1055/s-2002-34378

  日期：——

  A novel ansapeptide 6 was synthesized from tyrosine (5) and Bic 3b as the amino acid components and oxalic acid as the connecting link. The conformational properties of 6 were calculated by molecular mechanics.

  以酪氨酸(5)和Bic 3b为氨基酸成分，草酸为连接键，合成了一种新型的Ansapeptide 6。 通过分子力学计算了6的构象性质。
• A Bicyclic Cispentacin Derivative as a Novel Reverse Turn Inducer in a GnRH Mimetic
  作者：Oliver Langer、Hanspeter Kählig、Karen Zierler-Gould、Jan W. Bats、Johann Mulzer

  DOI：10.1021/jo025857o

  日期：2002.10.1

  A cispentacin-derived bicyclic beta-amino acid (Bic) has been synthesized and incorporated into the 6-position of GnRH. The new GnRH analogue has been characterized with respect to its structure in solution and its activity and affinity toward the human GnRH receptor.