[(1S,2R,3S,4R)-3-aminobicyclo[2.2.1]hept-2-yl]methanol | 357618-03-2

• 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: [(1S,2R,3S,4R)-3-aminobicyclo[2.2.1]hept-2-yl]methanol
• 英文别名: ((1S,2R,3S,4R)-3-aminobicyclo[2.2.1]heptan-2-yl)methanol；[(1S,2R,3S,4R)-3-amino-2-bicyclo[2.2.1]heptanyl]methanol
• CAS: 357618-03-2
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: QGMMKSUHQMVLRO-OSMVPFSASA-N

物化性质

• 沸点：
  241.0±13.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：

  [(1S,2R,3S,4R)-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
  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-exo-(1S,2R,3S,4R)-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 [(1S,2R,3S,4R)-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。
• Stereochemical studies.<b>58</b>. Saturated heterocycles.<b>39</b>. Preparation and steric structures of dihydro-1,3-oxazines, 1,3-oxazin-2-ones and 1,3-oxazine-2-thiones fused with norbornane and norbornene
  作者：Géza Stájer、Enikö A. Szabó、Ferenc Fülöp、Gábor Bernáth、Pál Sohár

  DOI：10.1002/jhet.5570200509

  日期：1983.9

  reduced with lithium aluminum hydride to the aminoalcohols 2 and 4; the latter were cyclized by means of arylimino ethers to methylene-bridged tetrahydro- (6a-c) and hexahydro-3,1-benzoxazines (7b-d), respectively. The endo (2) and exo (4) aminoalcohols were converted to methylene-bridged tetrahydro-3,1-benzoxazin-2-one (9) and hexahydro-3,1-benzoxazin-2-one (12) with ethyl chloroformate and sodium methoxide;

  3-内氨基双环[2.2.1]庚-5-烯-2-内羧酸（1），由内降冰片烯5-烯-2,3-二羧酸酐和类似的饱和顺式-外氨基酸（3）用氢化铝锂还原成氨基醇2和4 ; 后者通过芳胺基醚环化成亚甲基桥连的四氢-（6a-c）和六氢-3,1-苯并恶嗪（7b-d）。的内（2）和外（4）用氯甲酸乙酯和甲醇钠将氨基醇转化为亚甲基桥连的四氢-3,1-苯并恶嗪-2-酮（9）和六氢-3,1-苯并恶嗪-2-酮（12）；用二硫化碳对醇进行处理，通过二硫代氨基甲酸酯得到相应的2-硫酮（11、13）。结构通过红外光谱和核磁共振谱证实。
• 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。