(1R,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester | 158414-42-7

• 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,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester
• 英文别名: (+)-tert-butyl (1R,2S)-2-aminocyclopentane-1-carboxylate；(1R,2S)-(-)-tert-butyl 2-aminocyclopentanecarboxylate；tert-butyl (1R,2S)-2-aminocyclopentane-1-carboxylate；tert-butyl (1R,2S)-2-aminocyclopentanecarboxylate
• CAS: 158414-42-7
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: TUOXUKFPVXCENT-SFYZADRCSA-N

物化性质

• 沸点：
  240.3±33.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 16.0h， 以95%的产率得到(1R,2S)-2-氨基-1-环戊烷羧酸
  参考文献：
  名称：

  （–）-（1 R，2 S）-顺喷他星及其相关顺式和反式-2-氨基环戊烷和环己烷-1-羧酸的不对称合成

  摘要：

  抗真菌抗生素（–）-（1 R，2 S）-2-氨基环戊烷-1-羧酸（顺喷塔星）8及其环己烷同系物14是通过高立体选择性共轭加成手性锂N-苄基-N-制备的。 α-甲基苄基酰胺5。还通过顺式-β-氨基酯缀合物加成产物的选择性差向异构化制备了相应的反式-β-氨基酸10和16。

  DOI：

  10.1039/p19940001411
• 作为产物：
  描述：

  tert-butyl (1R,2S)-2-[N-benzyl-N-(α-methylbenzyl)amino]cyclopentane-1-carboxylate 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以93%的产率得到(1R,2S)-2-aminocyclopentanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction

  摘要：

  对β-氨基酸框架内取代效应的系统研究表明，β2-和β3-氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性较低至合理。这些结果促使对构象受限的β-氨基酸(1R,2S)-cispentacin进行评估，该氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性与L-脯氨酸相比相当或更高。

  DOI：

  10.1039/b711171a

文献信息

• ORNITHINE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP2141147A1

  公开（公告）日：2010-01-06

  Provided is a compound which is useful as a therapeutic agent for chronic renal insufficiency and a therapeutic agent for diabetic nephropathy. The present inventors have made extensive studies on an ornithine derivative having an antagonistic action against an EP4 receptor, and as a result, they have found that by introducing cycloalkanediyl at a C terminal of the ornithine part of the compound of the present invention, the physicochemical properties such as solubility, and the like can be improved, thereby giving further preferred properties as a pharmaceutical. Therefore, they have completed the present invention. The compound of the present invention exhibits a good antagonistic action against an EP4 receptor, and thus, it is useful as a therapeutic agent for chronic renal insufficiency and diabetic nephropathy.

  提供了一种化合物，可用作慢性肾功能不全的治疗剂和糖尿病肾病的治疗剂。目前的发明人对具有对EP4受体拮抗作用的鸟氨酸衍生物进行了广泛研究，结果发现通过在目前发明的化合物的鸟氨酸部分的C末端引入环烷基，可以改善物理化学性质，如溶解性等，从而赋予其作为药物的更优越性质。因此，他们完成了这项发明。目前发明的化合物对EP4受体表现出良好的拮抗作用，因此，它可用作慢性肾功能不全和糖尿病肾病的治疗剂。
• N-Allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoatesElectronic supplementary information (ESI) available: general procedure for addition reaction, deallylation, silylation of allylamine and data for compounds. See http://www.rsc.org/suppdata/cc/b4/b405347h/
  作者：Hirohisa Doi、Takeo Sakai、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1039/b405347h

  日期：——

  The chiral ligand controlled asymmetric conjugate addition reaction of lithium N-allyl-N-(tert-butyldimethylsilyl)amide to alkenoates proceeded smoothly to give, after protodesilylation, the corresponding 3-allylaminoalkanoates with high enantioselectivities in high yields. The allyl group on the nitrogen atom was easily removable to afford 3-aminoalkanoates.

  手性配体催化的锂N-烯丙基-N-(叔丁基二甲基硅基)胺与烯酯的非对称共轭加成反应顺利进行，经过脱硅化处理后，得到相应的3-烯丙基氨基烷酸酯，具有高的对映选择性和高的产率。氮原子上的烯丙基很容易被去除，从而获得3-氨基烷酸酯。
• TAN-1496 A, C and E, diketopiperazine antibiotics with inhibitory activity against mammalian DNA topoisomerase I.
  作者：YASUNORI FUNABASHI、TAKASHI HORIGUCHI、SHIGEMI IINUMA、SEIICHI TANIDA、SETSUO HARADA

  DOI：10.7164/antibiotics.47.1202

  日期：——

  Fungal metabolites with an epi-oligothiadiketopiperazine structure, TAN-1496 A, C and E, were isolated from the culture broth of Microsphaeropsis sp. FL-16144. Their molecular formulas were determined to be C22H28N2O9S2, C22H28N2O9S3 and C22H28N2O9S4, respectively. Structures were determined by comparing the NMR data with those of known diketopiperazine antibiotics, sirodesmins. These metabolites inhibited the relaxation of supercoiled pBR322 DNA by calf thymus topoisomerase I but did not affect the decatenation of kinetoplast DNA by calf thymus topoisomerase II at concentration up to 500μM. They strongly suppressed the growth of various murine and human tumor cells and induced apoptosis. Moreover, various derivatives were synthesized to investigate the relationship of their functional groups and biological activities.

  从 Microsphaeropsis sp. 的培养液中分离出具有表寡硫二酮哌嗪结构的真菌代谢物 TAN-1496 A、C 和 E。 FL-16144。它们的分子式分别确定为C22H28N2O9S2、 S3和 S4。通过将 NMR 数据与已知的二酮哌嗪类抗生素西罗结斯明进行比较来确定结构。这些代谢物在浓度高达 500μM 时抑制小牛胸腺拓扑异构酶 I 对超螺旋 pBR322 DNA 的松弛，但不影响小牛胸腺拓扑异构酶 II 对动质体 DNA 的去连接。它们强烈抑制各种小鼠和人类肿瘤细胞的生长并诱导细胞凋亡。此外，合成了各种衍生物以研究其官能团与生物活性的关系。
• Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid
  作者：Elin Abraham、Stephen G. Davies、Paul M. Roberts、Amber L. Thompson、James E. Thomson

  DOI：10.1007/s10870-011-0164-x

  日期：2011.11

  Crystals of the dimeric β-peptides 13 and 20, derived from (1R,2S)-2-aminocyclopentanecarboxylic acid and (1S,2R,3S)-2-amino-3-methylcyclopentanecarboxylic acid, respectively, were synthesised and studied by X-ray diffraction in order to establish their solid state secondary structural characteristics. Compound 13 crystallises in the monoclinic space group P 2 1 with cell parameters of a = 5.2682(1) Å, b = 9.1211(2) Å, c = 22.4467(6) Å, β = 91.3855(9)°, V = 1078.29(4) Å3 and Z = 2. Compound 20 crystallizes in the orthorhombic space group P 2 1 2 1 2 1 with cell parameters of a = 5.0968(1) Å, b = 11.5546(2) Å, c = 43.5414(8) Å, V = 2564.22(8) Å3 and Z = 4. In both cases adjacent molecules are linked by a series of N–H···O=C hydrogen bonds to form β-sheet like structures. The structures of two dipeptides derived from the β-amino acids (1R,2S)-2-aminocyclopentanecarboxylic acid and (1S,2R,3S)-2-amino-3-methylcyclopentanecarboxylic acid have been analysed by X-ray diffraction.

  为了确定其固态二级结构特征，我们合成了分别来自(1R,2S)-2-氨基环戊烷羧酸和(1S,2R,3S)-2-氨基-3-甲基环戊烷羧酸的二聚 β 肽 13 和 20 的晶体，并对其进行了 X 射线衍射研究。化合物 13 在单斜空间群 P 2 1 中结晶，晶胞参数为 a = 5.2682(1) Å，b = 9.1211(2) Å，c = 22.4467(6) Å，β = 91.3855(9)°，V = 1078.29(4) Å3，Z = 2。化合物 20 在正交空间群 P 2 1 2 1 2 1 中结晶，晶胞参数为 a = 5.0968(1) Å，b = 11.5546(2) Å，c = 43.在这两种情况下，相邻分子通过一系列 N-H-O=C 氢键相连，形成类似 β 片状结构。X 射线衍射分析了从 β-氨基酸 (1R,2S)-2- 氨基环戊烷羧酸和 (1S,2R,3S)-2-氨基-3-甲基环戊烷羧酸衍生的两种二肽的结构。
• Ornithine derivative
  申请人：Astellas Pharma Inc.

  公开号：US08030489B2

  公开（公告）日：2011-10-04

  Provided is a compound which is useful as a therapeutic agent for chronic renal insufficiency and a therapeutic agent for diabetic nephropathy. The present inventors have made extensive studies on an ornithine derivative having an antagonistic action against an EP4 receptor, and as a result, they have found that by introducing cycloalkanediyl at a C terminal of the ornithine part of the compound of the present invention, the physicochemical properties such as solubility, and the like can be improved, thereby giving further preferred properties as a pharmaceutical. Therefore, they have completed the present invention. The compound of the present invention exhibits a good antagonistic action against an EP4 receptor, and thus, it is useful as a therapeutic agent for chronic renal insufficiency and diabetic nephropathy.

  提供的是一种化合物，可用作慢性肾功能不全的治疗剂和糖尿病肾病的治疗剂。本发明人对具有对抗EP4受体作用的鸟氨酸衍生物进行了广泛的研究，结果发现通过在化合物的鸟氨酸部分的C末端引入环状烷基，可以改善其物理化学性质，例如溶解度等，从而赋予其更优越的药物特性。因此，他们完成了本发明。本发明的化合物显示出良好的对抗EP4受体的作用，因此可用作慢性肾功能不全和糖尿病肾病的治疗剂。