(1R,2R,5R,7R)-2-amino-6,6-dimethylbicyclo[3.3.1]heptane-3-carboxylic acid | 1027343-73-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,5R,7R)-2-amino-6,6-dimethylbicyclo[3.3.1]heptane-3-carboxylic acid
• 英文别名: (1R,2R,3R,5R)-2-amino-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid；(1R,2R,3R,5R)-2-amino-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxylic acid
• CAS: 1027343-73-2
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: QWGOAXBNSBIKLN-YWIQKCBGSA-N

物化性质

• 熔点：
  250-252 °C(Solv: acetone (67-64-1); water (7732-18-5))
• 沸点：
  302.6±25.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (1R,2R,5R,7R)-2-amino-6,6-dimethylbicyclo[3.3.1]heptane-3-carboxylate 在 水 作用下， 生成 (1R,2R,5R,7R)-2-amino-6,6-dimethylbicyclo[3.3.1]heptane-3-carboxylic acid
  参考文献：
  名称：

  两性离子手性固定相ZWIX（+）和ZWIX（–）上受约束的β-氨基酸对映体的异常温度诱导保留行为。

  摘要：

  研究了温度对两性离子型[Chiralpak ZWIX（+）和ZWIX（-）]手性固定相上环状β-氨基酸对映体的手性识别的影响。实验是在不同的流动相组成下，在10°C的柱温下，在10–50°C的温度范围内进行的。根据ln k和lnα与1 / T的关系图计算了表观热力学参数和T iso值，分别。观察到异常的温度行为，尤其是在ZWIX（–）色谱柱上，在该色谱柱上使用包含25 mM三乙胺和50 mM甲酸作为流动相的MeOH / MeCN（50/50 v / v）导致了非线性Van't Hoff图并随着温度的升高而延长保留时间。在两根色谱柱上，均观察到了焓和熵驱动的分离。手性26：385–393，2014。©2014 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22333

文献信息

• Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives
  作者：Zsolt Szakonyi、Tamás A. Martinek、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2008.09.026

  日期：2008.10

  Chlorosulfonyl isocyanate addition to (−)- and (+)-apopinene furnished monoterpene-fused β-lactams in highly regio- and stereospecific reactions. β-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino

  （-）-和（+）-Apopinene的氯磺酰基异氰酸酯可在高度区域和立体特异性反应中提供单萜融合的β-内酰胺。β-内酰胺5和13的反应性类似于环烷烃融合类似物，并易于转化为β-氨基酸及其受保护的衍生物。顺式-氨基酯的碱催化异构化以优异的产率提供了相应的反式-氨基酸对映体。完全的异构化是由稳定性差异解释的，该稳定性差异是由顺式和反式非对映异构体之间的从头算计算得出的。
• WO2008/59299
  申请人：——

  公开号：——

  公开（公告）日：——
• Chiral cyclic beta-amino acids and their derivates, pharmaceutical compositions containing them and the use of such compounds
  申请人：Bioblocks Magyarország Gyógyszerkémiai És Fejleszto KFT

  公开号：EP2102147B1

  公开（公告）日：2011-06-22
• Chiral Cyclic Beta-Amino Acids and their Derivatives, Pharmaceutical Compositions Containing Them and the Use of Such Compounds
  申请人：Fulop Ferenc

  公开号：US20100081717A1

  公开（公告）日：2010-04-01

  The invention relates to chiral cyclic β-amino acids of Formula (I) and their salts formed with pharmaceutically acceptable acids or bases, wherein the main meanings of the substituents are as follows: R stands for C 1-4 Alk; X stands for —COOH, —CONH 2 , —CONH(C 1-4 Alk), —CON(C 1-4 Alk) 2 , —COO(C 1-4 Alk), —COPhe-O-(C 1-4 Alk) or —CH 2 OH; Y stands for —NH 2 , —NHBoc, —NHFmoc, —NH(C 1-4 Alk), —N(C 1-4 Alk) 2 , —NHCH 2 Ph, or Ar—NH—C(=X 0 )—N(R 0 )— wherein Ar stands for a phenyl group substituted by C 1-4 alkoxy or halogen, X 0 stands for O or S, and R 0 stands for hydrogen or benzyl; and X+Y stands for —CONH— vagy —CON(Boc)-; with the proviso that when X stands for —COOH, then Y may be only different from —NH 2 . The invention also relates to pharmaceutical compositions having multidrug-resistance reversing effect that contain one or more compound(s) of Formula (I) or a salt thereof and inert pharmaceutical carriers and/or auxiliary agents. The invention also relates to carboxylic acids of Formula (XX) and their salts.
• US8183292B2
  申请人：——

  公开号：US8183292B2

  公开（公告）日：2012-05-22