3S,4S-dimethoxy-pyrrolidine | 596793-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3S,4S-dimethoxy-pyrrolidine
• 英文别名: (3S,4S)-3,4-dimethoxypyrrolidine
• CAS: 596793-29-2
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: CROOPTGQTSCWCM-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3S,4S-dimethoxy-pyrrolidine 在 盐酸 、 4-二甲氨基吡啶 、 copper(l) chloride 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 Phenyl-((3R,4S)-2,3,4-trimethoxy-pyrrolidin-1-yl)-methanone
  参考文献：
  名称：

  Exploratory Synthetic Studies of the α-Methoxylation of Amides via Cuprous Ion-Promoted Decomposition of o-Diazobenzamides

  摘要：

  A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting alpha-amidyl radical. The transformation produces alpha-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (-)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give a-methoxylated amide substrates 19a/ 19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.

  DOI：

  10.1021/jo961529a
• 作为产物：
  描述：

  3S,4S-dimethoxy-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium 10% on activated carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3S,4S-dimethoxy-pyrrolidine
  参考文献：
  名称：

  Indolyl-urea derivatives of thienopyridines useful as antiangiogenic agents, and methods for their use

  摘要：

  这项发明涉及由公式I表示的化合物，以及这些化合物的前药、药学上可接受的盐或溶剂，其中X、R1和R11如本文所定义。该发明还涉及含有公式I化合物的药物组合物，以及通过给予公式I化合物来治疗哺乳动物的过度增殖性疾病的方法。

  公开号：

  US20040019065A1

文献信息

• [EN] AMINOPYRIMIDINE HETEROCYCLIC COMPOUND WITH ADENOSINE RECEPTOR ANTAGONISTIC ACTIVITY<br/>[FR] COMPOSÉ AMINOPYRIMIDINE HÉTÉROCYCLIQUE PRÉSENTANT UNE ACTIVITÉ ANTAGONISTE DU RÉCEPTEUR DE L'ADÉNOSINE
  申请人：SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI

  公开号：WO2017088755A1

  公开（公告）日：2017-06-01

  Disclosed hereinis an aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activity, comprising a compound of the general formula (I), or a pharmaceutically acceptable salt thereof. The aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activitydisclosed herein can be used as an effective adenosine receptor antagonist, and can be used for the treatment or prevention of disorders caused by abnormal level of adenosine.

  本文披露了一种具有腺苷受体拮抗活性的氨基嘧啶杂环化合物，包括一般式(I)的化合物或其药学上可接受的盐。本文披露的具有腺苷受体拮抗活性的氨基嘧啶杂环化合物可用作有效的腺苷受体拮抗剂，并可用于治疗或预防由腺苷水平异常引起的疾病。
• [DE] NEUE 2,5-DISUBSTITUIERTE PYRIMIDINDERIVATE<br/>[EN] NOVEL 2,5-DISUBSTITUTED PYRIMIDINE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE PYRIMIDINE 2,5-DISUBSTITUES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004009589A1

  公开（公告）日：2004-01-29

  Die vorliegende Erfindung betrifft neue 2,5-disubstituierte Pyrimidin-Derivate, welche die lösliche Guanylatcyclase stimulieren, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln, insbesondere von Arzneimittel zur Behandlung von Krankheiten des Zentralnervensystems.

  本发明涉及新的2,5-二取代嘧啶衍生物，可刺激可溶性鸟苷酸环化酶，以及其制备方法和用途，特别是用于制备治疗中枢神经系统疾病的药物。
• 2,5-DISUBSTITUTED PYRIMIDINE DERIVATIVES
  申请人：Feurer Achim

  公开号：US20060167016A1

  公开（公告）日：2006-07-27

  The present invention relates to novel 2,5-disubstituted pyrimidine derivatives which stimulate soluble guanylate cyclase, to processes for the preparation thereof, and to the use thereof for producing medicaments, in particular medicaments for the treatment of central nervous system diseases.

  本发明涉及新型的2,5-二取代嘧啶衍生物，其可以刺激可溶性鸟苷酸环化酶的活性，以及其制备方法和用于制备药物的用途，特别是用于治疗中枢神经系统疾病的药物。
• VLA-4 INHIBITORY DRUG
  申请人：Machinaga Nobuo

  公开号：US20090233901A1

  公开（公告）日：2009-09-17

  There is provided a VLA-4 inhibitory drug having good oral absorbability and exhibiting sufficient anti-inflammatory effects when administered orally. A compound represented by the following formula (I): wherein R 1 represents a hydrogen atom or a C1-8 alkyl group; R 2 represents a hydrogen atom, a halogen atom, a C1-8 alkoxy group, or a benzyloxy group which may be substituted; Q represents a monocyclic or bicyclic nitrogen-containing heterocyclic group which may be substituted, and has a nitrogen atom as the bonding site; Y represents an oxygen atom or CH 2 ; W represents a bicyclic aromatic hydrocarbon ring group which may be substituted, or a bicyclic aromatic heterocyclic group which may be substituted; R 3a , R 3b and R 3c each independently represent a hydrogen atom, a halogen atom, a C1-8 alkoxy group or a C1-8 alkyl group; and A 1 represents a nitrogen atom or C—R 3d (wherein R 3d represents a hydrogen atom, a halogen atom, a C1-8 alkoxy group or a C1-8 alkyl group), or a salt thereof, or a VLA-4 inhibitory drug comprising the compound or the salt as an active ingredient.

  提供了一种VLA-4抑制剂药物，具有良好的口服吸收性，并在口服给药时表现出足够的抗炎效果。其中，化合物的表示式如下（I）：其中，R1表示氢原子或C1-8烷基；R2表示氢原子、卤素原子、C1-8烷氧基或可取代的苄氧基；Q表示可取代的单环或双环含氮杂环基团，并具有氮原子作为键合位点；Y表示氧原子或CH2；W表示可取代的双环芳香烃环基团或可取代的双环芳香杂环基团；R3a、R3b和R3c分别独立地表示氢原子、卤素原子、C1-8烷氧基或C1-8烷基；A1表示氮原子或C-R3d（其中，R3d表示氢原子、卤素原子、C1-8烷氧基或C1-8烷基），或其盐，或包含该化合物或其盐作为活性成分的VLA-4抑制剂药物。
• VLA-4 inhibitory drug
  申请人：Machinaga Nobuo

  公开号：US20130065882A1

  公开（公告）日：2013-03-14

  This invention relates to a VLA-4 inhibitory drug, having good oral absorbability and exhibiting sufficient anti-inflammatory effects when administered orally, wherein an active ingredient is represented by formula (I), or a salt thereof: Q represents an optionally-substituted monocyclic or bicyclic nitrogen-containing heterocyclic group having a nitrogen atom as the bonding site; Y represents an oxygen atom or CH 2 ; W represents an optionally-substituted bicyclic aromatic hydrocarbon ring group or an optionally-substituted bicyclic aromatic heterocyclic group; A 1 represents a nitrogen atom or C—R 3d wherein R 3d represents a hydrogen atom, a halogen atom, a C1-8 alkoxy group or a C1-8 alkyl group; R 1 represents H or a C1-8 alkyl group; R 2 represents H, a halogen, a C1-8 alkoxy

  本发明涉及一种VLA-4抑制剂药物，具有良好的口服吸收性，并在口服给药时展现足够的抗炎效果，其中活性成分由公式（I）或其盐表示： Q代表一个可选取代的含氮杂环基团，其为单环或双环结构，其中氮原子为键合位点； Y代表一个氧原子或CH2； W代表一个可选取代的双环芳香烃环基团或可选取代的双环芳香杂环基团； A1代表一个氮原子或C-R3d，其中R3d代表氢原子、卤素原子、C1-8烷氧基团或C1-8烷基团； R1代表氢原子或C1-8烷基团； R2代表氢原子、卤素原子、C1-8烷氧基团或C1-8烷基团。