[(1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-2-yl]methanol | 95630-79-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-2-yl]methanol
• 英文别名: ((1R,2R,3S,4S)-3-aminobicyclo[2.2.1]heptan-2-yl)methanol；[(1R,2R,3S,4S)-3-amino-2-bicyclo[2.2.1]heptanyl]methanol
• CAS: 95630-79-8
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: QGMMKSUHQMVLRO-CWKFCGSDSA-N

物化性质

• 沸点：
  241.0±13.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-2-yl]methanol 在 氢氧化钾 、 碘甲烷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (1R,2R,7S,8S)-5-Oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-(4Z)-ylidene-phenyl-amine
  参考文献：
  名称：

  Sohar, Pal; Stajer, Geza; Szabo, Angela E., Journal of the Chemical Society. Perkin transactions II, 1987, p. 599 - 606

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl di-endo-(1R,2R,3S,4S)-3-aminobicyclo[2.2.1]heptane-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 [(1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-2-yl]methanol
  参考文献：
  名称：

  Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media

  摘要：

  N-Protected racemic di-exo- and di-endo-3-aminobicyclo[2.2.1]heptane-2-methanols and di-exo- and di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanols were resolved through lipase-catalysed O-acylation, using vinyl butyrate in organic solvents. Of the lipases screened most showed a preference for the (2S)-enantiomer. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00093-3

文献信息

• [EN] HEPATITIS B CAPSID ASSEMBLY MODULATORS<br/>[FR] MODULATEURS D'ASSEMBLAGE DE CAPSIDE DE L'HÉPATITE B
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2021119081A1

  公开（公告）日：2021-06-17

  Described herein are hepatitis B capsid assembly modulators and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of hepatitis B.

  本文描述了乙型肝炎壳蛋白组装调节剂和包含该类化合物的药物组合物。这些化合物和组合物对于治疗乙型肝炎是有用的。
• Structures of Saturated 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones Prepared from 4-Oxopentanoic Acid and Cyclic Amino Alcohols
  作者：Henri Kivelä、Karel D. Klika、Angela Szabó、Géza Stájer、Kalevi Pihlaja

  DOI：10.1002/ejoc.200200662

  日期：2003.5

  Saturated heterocycles containing two condensed heterocyclic rings and a carbo(bi)cyclic ring have been prepared by the reaction of 4-oxopentanoic acid (1) with (bi)cyclic amino alcohols. 5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones 2−5 were formed in the reaction of 1 with trans- or cis-2-(hydroxymethyl)cyclohexylamines or -cyclohexenylamines. With di-endo- or di-exo-3-aminobicyclo[2.2.1]hept-2-yl-

  含有两个稠合杂环和一个碳（双）环的饱和杂环已通过 4-氧代戊酸（1）与（双）环氨基醇的反应制备。5H-Pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones 2-5 是在 1 与反式或顺式-2-（羟甲基）环己胺或-环己烯胺的反应中形成的。使用 di-endo- 或 di-exo-3-aminobicyclo[2.2.1]hept-2-yl- 或 -hept-5-en-2-ylmethanols，1 产生了相应的衍生物 6-9，它们在环己烷或环己烯环。合成的立体选择性高；只有 5、7 和 9 两种 C-3a 差向异构体均以可观察的量产生。通过应用标准脉冲技术通过NMR光谱方法建立结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Ring-chain tautomerism and three- to four-component equilibria in fused-ring tetrahydro-1,3-oxazines
  作者：Kalevi Pihiaja、Aija Parkkinen、Ferenc Fülöp、Jonna Mattinen、Gábor Bernath

  DOI：10.1016/s0040-4020(01)86442-5

  日期：1991.1

  aldehydes led to ring-chain tautomeric equilibria between epimeric tetrahydro-1,3-oxazines and open-chain Schiff bases, in all cases the equilibrium mixtures consisted of two epimeric ring forms although the 2-axial epimers of the cyclohexene-fused derivatives had only a minor contribution to the ring-chain tautomeric equilibria. For the norbornane-fused derivatives the ring-chain tautomeric equilibria were

  的缩合- （1）和-2-羟甲基-4-环己烯基-1-胺（2）和2,3- - （3）和2,3- -3- hydroxymethylbicyclo [2.2.1]庚胺（ 4）与8种不同的芳族醛导致差向异构四氢-1,3-恶嗪和开链席夫碱之间的环链互变异构平衡，在所有情况下，平衡混合物均由两种差向异构环形式组成，尽管环己烯稠合的衍生物对环链互变异构平衡的贡献很小。对于降冰片烷稠合的衍生物，取环链互变异构平衡为等于环形式之和与开环形式的E-异构体之比，在这种情况下，简单方程为log K X =0.76σ + +日志K对于每个研究的系统，X = H最近在1,3-恶嗪中普遍用于环链互变异构。
• Application of t-2-benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid for the preparation of saturated isoindole-fused heterocyclesDedicated to Professor András Messmer on the occasion of his 80th birthday.
  作者：Géza Stájer、Angela E. Szabó、Ferenc Csende、Gyula Argay、Pál Sohár

  DOI：10.1039/b107293p

  日期：2002.2.25

  t-2-Benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid 1 reacts with cis-2-aminocyclohexanemethanol to give the saturated cis-isoindolo[2,1-a][3,1]benzoxazine 2. Reaction of 1 with trans-2-aminocyclohex-4-enemethanol yields three diastereomeric isoindolo derivatives 3a–c. Cyclization of 1 with 1,3-diaminopropane results in a diastereomeric mixture of cis-pyrimido[1,2-a]isoindolones 4a,b. With di-endo-norbornane aminoalcohol, 1 reacts to yield a mixture of cis- and trans-annelated diastereomers 5 and 6. In its reactions with di-exo-norbornane and norbornene aminoalcohols, 1 isomerizes to give cis-condensed isoindolo derivatives 7–10. After isolation, the structures were established by 1H and 13C NMR spectroscopy, with up-to-date measuring techniques such as NOEDIF, DEPT, HMQC, 2D-NOESY, 2D-COSY and HMBC and, for 10, X-ray measurements. The results show that, with two exceptions, the trans acid 1 undergoes isomerization to give cis-condensed products.

  t-2-苯甲酰-t-5-苯基环己烷-r-1-羧酸1与顺-2-氨基环己醇反应，生成饱和的顺-异吲哚并[2,1-a][3,1]苯并噁唑啉2。1与反-2-氨基环己-4-烯醇反应生成三个非对映异构体的异吲哚衍生物3a–c。1与1,3-二氨基丙烷环化反应生成一种非对映异构体混合物的顺-吡咯并[1,2-a]异吲哚酮4a,b。与二-内环诺烷氨醇反应，1生成顺-和反-环状非对映异构体的混合物5和6。在与二-外环诺烷和诺烯氨醇的反应中，1异构化生成顺-缩合异吲哚衍生物7–10。经过分离后，利用1H和13C NMR光谱法以及最新的测量技术如NOEDIF、DEPT、HMQC、2D-NOESY、2D-COSY和HMBC，以及对于10的X射线测量确定了结构。结果表明，除了两个例外，转酸1发生异构化，生成顺缩合产物。
• Pharmaceutically active pyrrolidine derivatives as bax inhibitors
  申请人：——

  公开号：US20030171309A1

  公开（公告）日：2003-09-11

  The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating-up to an inhibitory-activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CR<6>R<7>, NOR<6>, NNR<6>R<7>; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO2-, —SO2NH—; —CH2-; B is either a group —(C═O)—NR<8>R<9> or represents a heterocyclic residue having the formula (II) wherein Q is NR<10>, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.

  本发明涉及新的取代吡咯烷衍生物的化学式(I)。所述化合物通常用作药用活性化合物。具体来说，化学式(I)的吡咯烷衍生物在治疗和/或预防神经退行性疾病、与多谷氨酸氨基酸序列相关的疾病、癫痫、缺血、不孕症、心血管疾病、肾脏缺氧、肝炎和艾滋病方面具有用处。所述吡咯烷衍生物显示出对细胞死亡促进子Bax和/或导致Bax激活途径的调节作用，最显著地是下调至抑制活性，并因此允许阻止细胞色素(c)的释放。本发明还涉及新的具有药用活性的取代吡咯烷衍生物，以及它们的制备方法，其中X选自O、S、CR<6>R<7>、NOR<6>、NNR<6>R<7>组成的群；A选自—(C═O)—、—(C═O)—O—、—C(═NH)—、—(C═O)—NH—、—(C═S)—NH、—SO2-、—SO2NH—；—CH2-；B是一个群—(C═O)—NR<8>R<9>或代表具有化学式(II)的杂环残基，其中Q是NR<10>、O或S；n是选自0、1或2的整数；Y、Z和E与它们连接的两个碳共同形成一个5-6成员芳香族或杂芳族环。