3-[(benzyloxy)methyl]-5-methyl-1-[(1S,5S,8S)-3-oxo-2-azabicyclo[3.3.1]nonan-8-yl]pyrimidine-2,4(1H,3H)-dione | 221300-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-[(benzyloxy)methyl]-5-methyl-1-[(1S,5S,8S)-3-oxo-2-azabicyclo[3.3.1]nonan-8-yl]pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(S,S,S)-8-azabicyclo[3.3.1]nonan-7-on-2-yl]-3-[(benzyloxy)methyl]thymine；5-methyl-1-[(1S,5S,8S)-3-oxo-2-azabicyclo[3.3.1]nonan-8-yl]-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 221300-97-6
• 化学式: C₂₁H₂₅N₃O₄
• 分子量: 383.447
• InChiKey: PSCAMHGVLIMSNG-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(benzyloxy)methyl]-5-methyl-1-[(1S,5S,8S)-3-oxo-2-azabicyclo[3.3.1]nonan-8-yl]pyrimidine-2,4(1H,3H)-dione 在 4-二甲氨基吡啶 、 lithium hydroxide 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.75h， 生成 (1S,3S,4S)-4-{3-[(benzyloxy)methyl]-1,2,3,4-tetrahydro-5-methyl-2,4-dioxopyrimidin-1-yl}-3-{[(tert-butoxy)carbonyl]amino}cyclohexane acetic acid
  参考文献：
  名称：

  摘要：

  Cyclic nucreo-delta-amino acids that constitute monomers of a conformationally constrained nucleo-delta-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective epsilon-iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through S(N)2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.

  DOI：

  10.1002/1522-2675(20000607)83:6<1049::aid-hlca1049>3.0.co;2-1
• 作为产物：
  描述：

  (1S)-cyclohex-3-eneacetonitril 在 4-二甲氨基吡啶 、 Raney-Cu 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 148.58h， 生成 3-[(benzyloxy)methyl]-5-methyl-1-[(1S,5S,8S)-3-oxo-2-azabicyclo[3.3.1]nonan-8-yl]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  摘要：

  Cyclic nucreo-delta-amino acids that constitute monomers of a conformationally constrained nucleo-delta-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective epsilon-iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through S(N)2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.

  DOI：

  10.1002/1522-2675(20000607)83:6<1049::aid-hlca1049>3.0.co;2-1

文献信息

• Supramolecular pairing system, its preparation and use
  申请人：Nanogen Recognomics GmbH

  公开号：US06689884B1

  公开（公告）日：2004-02-10

  The invention relates to a compound of formula (I), wherein R1 is NR3R4, OR3 or SR3 with R3 and R4 being H or CnH2n+1 independently of each other and being the same or different, n being a whole number from 1 to 12; R2 is equal to CmH2m—C(X)—Y with X being ═O, ═S or ═N, Y being equal to OR3, NR3R4 or SR3, R3 and R4 having the same meaning given above, and m being a whole number from 1 to 4; or R2 is equal to CmH2m—Z—Y′ with Z being a sulfonyl, phosphonyl, ether or amine group, Y′ being equal to H, CnH2n+1, OR3, NR3R4 or SR3 then Z is sulphonyl or phosphonyl group, n, R3 and R4 having the meaning given above, and Y′ being equal to CnH2n+1 when Z is an ether or an amine group; A, B, and D are the same or different and mean CR5R6, O, NR7 ou S independently of each other with R5, R6 and R7 being H or CnH2n+1, independently of each other, n having the meaning given above; and C is equal to CR8 or N with R8 having the meaning of R5 independently, A—B, B—C or C—D not being two identical heteroatoms; and nucleobase means thymine, uracile, adenine, cytosine, guanine, isocytosine, isoguanine, xanthine or hypoxanthine. The invention also relates to a method for producing these derivatives and to their use in pairing and/or testing systems.

  本发明涉及一种式为(I)的化合物，其中R1是NR3R4，OR3或SR3，其中R3和R4分别独立地为H或CnH2n+1，且相同或不同，n是1至12的整数；R2等于CmH2m-C(X)-Y，其中X是O、S或N，Y等于OR3、NR3R4或SR3，其中R3和R4具有上述相同的含义，m是1至4的整数；或R2等于CmH2m-Z-Y'，其中Z是磺酰基、膦酰基、醚基或胺基，Y'等于H、CnH2n+1、OR3、NR3R4或SR3，然后Z是磺酰基或膦酰基，n、R3和R4具有上述含义，当Z是醚基或胺基时，Y'等于CnH2n+1；A、B和D相同或不同，分别表示CR5R6、O、NR7或S，其中R5、R6和R7相互独立，且均为H或CnH2n+1，n具有上述含义；C等于CR8或N，其中R8具有与R5相同的含义，A-B、B-C或C-D不是两个相同的杂原子；核碱基表示胸腺嘧啶、尿嘧啶、腺嘌呤、胞嘧啶、鸟嘌呤、异胞嘧啶、异鸟嘌呤、黄嘌呤或次黄嘌呤。本发明还涉及一种生产这些衍生物的方法以及它们在配对和/或测试系统中的使用。
• US6689884B1
  申请人：——

  公开号：US6689884B1

  公开（公告）日：2004-02-10
• US7439345B2
  申请人：——

  公开号：US7439345B2

  公开（公告）日：2008-10-21
• ——
  作者：Gunter Karig、Andreas Fuchs、Arne Büsing、Tilmann Brandstetter、Stefan Scherer、Jan W. Bats、Albert Eschenmoser、Gerhard Quinkert

  DOI：10.1002/1522-2675(20000607)83:6<1049::aid-hlca1049>3.0.co;2-1

  日期：2000.6.7

  Cyclic nucreo-delta-amino acids that constitute monomers of a conformationally constrained nucleo-delta-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective epsilon-iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through S(N)2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.