methyl (<<(tert-butoxy)carbonyl>amino>methyl)cyclopropane-1-carboxylate | 220145-17-5

• 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: methyl (<<(tert-butoxy)carbonyl>amino>methyl)cyclopropane-1-carboxylate
• 英文别名: methyl 1-({[(tert-butoxy)carbonyl]amino}methyl)cyclopropane-1-carboxylate；methyl 1-(((tert-butoxycarbonyl)amino)methyl)cyclopropanecarboxylate；Methyl 1-((tert-butoxycarbonylamino)methyl)cyclopropanecarboxylate；methyl 1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylate
• CAS: 220145-17-5
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: BNFKQAZMTSXVIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (<<(tert-butoxy)carbonyl>amino>methyl)cyclopropane-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 1-(氨甲基)环丙烷甲酸甲酯盐酸盐
  参考文献：
  名称：

  [1,2,4]THIADIAZINE 1,1-DIOXIDE COMPOUNDS

  摘要：

  这项发明涉及[1,2,4]噻二嗪1,1-二氧化物化合物和含有这种化合物的药物组合物，可用于治疗丙型肝炎病毒感染。

  公开号：

  US20090306057A1
• 作为产物：
  描述：

  1-氰基-1-环丙烷羧酸 在 镍 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙腈 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 6.0h， 生成 methyl (<<(tert-butoxy)carbonyl>amino>methyl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Preparation and Structure ofβ-Peptides Consisting of Geminally Disubstitutedβ2,2- andβ3,3-Amino Acids: A Turn Motif forβ-Peptides

  摘要：

  We report on the synthesis of new and previously described beta-peptides (1-6), consisting of up to twelve beta(2,2-) or beta(3,3)-geminally disubstituted beta-amino acids which do not fit into any of the secondary structural patterns of beta-peptides, hitherto disclosed. The required 2,2- and 3,3-dimethyl derivatives of 3-aminopropanoic acid are readily obtained from 3-methylbut-2-enoic acid and ammonia (Scheme 1) and from Boc-protected methyl 3-aminopropanoate by enolate methylation (Scheme 2). Protected (Boc for solution-, Fmoc for solid-phase syntheses) 1-(aminomethyl)cycloalkanecarboxylic-acid derivatives (with cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings) are obtained from 1-cyanocycloalkanecarboxylates and the corresponding dihaloalkanes (Scheme 3). Fully C-13- and N-15-labeled 3-amino-2,2-dimethylpropanoic-acid derivatives were prepared from the corresponding labeled precursors (see asterixed formula numbers and Scheme 4). Coupling of these amino acids was achieved by methods which we had previously employed for other beta-peptide syntheses ( intermediates 18 - 23). Crystal structures of Boc-protected geminally disubstituted amine acids (16a-d) and of the corresponding tripeptide (23a), as well as NMR and IR spectra of an isotopically labeled beta-hexapeptide (2a*) are presented (Figs. 1-4) and discussed. The tripeptide structure contains a ten-membered H-bonded ring which is proposed to be a turn-forming motif for beta-peptides (Fig. 2).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2218::aid-hlca2218>3.0.co;2-0

文献信息

• NOVEL 1,3-OXAZOLIDINE COMPOUNDS AND THEIR USE AS RENIN INHIBITORS
  申请人：Sun Piaoyang

  公开号：US20130005730A1

  公开（公告）日：2013-01-03

  The present invention relates to certain novel 1,3-oxazolidine compounds of formula (I), to processes for making such compounds and to their utility as renin inhibitors or prodrugs of renin inhibitors.

  本发明涉及一些新型1,3-噁唑啉化合物(I)的公式，制备这些化合物的方法以及它们作为肾素抑制剂或肾素抑制剂的前药的用途。
• sGC STIMULATORS
  申请人：IRONWOOD PHARMACEUTICALS, INC.

  公开号：US20160031903A1

  公开（公告）日：2016-02-04

  Compounds of Formulae I′ and I are described, which are useful as stimulators of sGC, particularly NO-independent, heme-dependent stimulators. These compounds are also useful for treating, preventing or managing various disorders that are herein disclosed.

  本文描述了化学式I'和I的化合物，它们可用作sGC的刺激剂，特别是NO独立，血红素依赖性的刺激剂。这些化合物还可用于治疗、预防或管理本文中披露的各种疾病。
• sGC stimulators
  申请人：Ironwood Pharmaceuticals, Inc.

  公开号：US10183021B2

  公开（公告）日：2019-01-22

  Compounds of Formulae I′ and I are described, which are useful as stimulators of sGC, particularly NO-independent, heme-dependent stimulators. These compounds are also useful for treating, preventing or managing various disorders that are herein disclosed.

  本文描述了式 I′ 和 I 的化合物，它们可用作 sGC 的刺激剂，特别是 NO 依赖性、血红素依赖性刺激剂。这些化合物还可用于治疗、预防或控制本文公开的各种疾病。
• [EN] SGC STIMULATORS<br/>[FR] STIMULATEURS DE SGC
  申请人：NAKAI TAKASHI

  公开号：WO2014144100A3

  公开（公告）日：2014-11-06
• Synthesis, Crystal Structures, and Modelling ofβ-Oligopeptides Consisting of 1-(Aminomethyl)cyclopropanecarboxylic Acid: Ribbon-Type Arrangement of Eight-Membered H-Bonded Rings
  作者：Stefan Abele、Paul Seiler、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1559::aid-hlca1559>3.0.co;2-a

  日期：1999.10.6

  Partially and fully protected, and unprotected beta-oligopeptides (3-9) were prepared from 1-(aminomethyl)cyclopropanecarboxylic acid, which, in turn, is readily available from cyanoacetate and dibromoethane. N-Boc and C-OMe protection were applied for the fragment-coupling (1-hydroxy-1H-benzotriazole (HOBt)/1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC)) solution synthesis. X-Ray crystal structures of the dimer (3), trimer (5), and tetramer (6) are described, and compared with those of the Boc-protected building blocks (2) and of the corresponding trimer (10) consisting of 1-(aminomethyl)cyclohexanecarbonyl residues (cf. Figs. 1 and 2). While the cyclohexane derivative forms ten-membered hydrogen-bonded rings, the characteristic secondary-structural motif in the cyclopropane derivatives is an eight-membered ring with H-bonding between next neighbors (Fig. 1). All cyclopropanecarbonyl moieties in the reported structures have the - generally more stable - s-cis ('bisected') conformation of the C=O groups on the three-membered rings (not preferred with the cyclohexane analog, the exocyclic CO group of which may be in an s-trans, a perpendicular, an axial, or an equatorial position). The bisecting effect and the large exocyclic bond angle (120 degrees) in the cyclopropane units are proposed to provide the 'ordering' elements - on top of the staggering effect of the C(2)-C(3) ethane bond in all beta-peptides - which lead to the observed substituent-induced turn formation. A high degree of intramolecular H-bonding is evident also from IR spectroscopy (Fig. 3), and concentration- and temperature-dependent NMR measurements (Fig. 4) of CHCl3 and CD2Cl2 solutions, indicating that the boat-type arrangement of the eight-membered rings with their unusual H-bonding geometry (Fig. 1, f) is also present in solution. A possible structure of a poly[1-(aminomethyl)cyclopropane-carboxylic acid] consisting of a flight of stairs formed by folded H-bonded eight-membered rings is modelled. using the oligomer X-ray data (Fig. 5). The type of secondary structure found in the solid state of the beta(2.2)-peptides reported here is unprecedented in the realm of alpha-peptides and proteins.