(+/-)-cis-1-[2-(hydroxymethyl)cyclohexyl]-5-bromouracil

• 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: (+/-)-cis-1-[2-(hydroxymethyl)cyclohexyl]-5-bromouracil
• 英文别名: 5-bromo-1-[(1R,2S)-2-(hydroxymethyl)cyclohexyl]pyrimidine-2,4-dione
• 化学式: C₁₁H₁₅BrN₂O₃
• 分子量: 303.156
• InChiKey: DAXDAJDSJAUHFP-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-cis-1-[2-(hydroxymethyl)cyclohexyl]-5-bromouracil 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以38%的产率得到(+/-)-cis-1H,6H-6a,7,8,9,10,10a-hexahydropyrimido[1,6-a][3,1]benzoxazin-1,3-(2H)-dione
  参考文献：
  名称：

  Regioselective synthesis of O2- and O6-cyclopyrimidine nucleoside analogues

  摘要：

  Regioselective synthesis of two new series of cyclonucleoside analogues from the 1,2-carbonucleoside of uracil 1a: O-2 7 '-cyclo-nucleosides (3a-c) and O-6 7 '-cyclonucleosides (4a-c), analogues of pyrimidine (cyclohexane derivatives) is reported. Synthesis Of O-2-cyclo- nucleoside analogues was performed by activation of the hydroxymethyl group of carbocyclic moiety and using the carbonyl group at position 2 of the heterocyclic base as a nucleophile. Synthesis of O-6-cyclonucleoside analogues was achieved by nucleophilic attack of the 7 '-hydroxyl group on the electron-deficient 6-position and subsequently dehydrohalogenation in basic conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.007
• 作为产物：
  描述：

  1-(R)-cis-2-aminocyclohexanemethanol 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.0h， 生成 (+/-)-cis-1-[2-(hydroxymethyl)cyclohexyl]-5-bromouracil
  参考文献：
  名称：

  核苷的 1-[2-(羟甲基)环己基]嘧啶类似物的合成：比较研究

  摘要：

  报道了一系列新的嘧啶（环己烷衍生物）的 1,2-二取代碳核苷类似物的合成。对于尿苷类似物 5a 的合成，在氨基醇 3 的氨基上或在前身 β-内酰胺 1 的酰胺基上构建碱基比碱基与受保护的二醇缩合更有效。5a 的顺式构型通过 X 射线晶体学证实。化合物 5a 在尿嘧啶 5 位被 Cl、Br 和 I 卤化。

  DOI：

  10.1055/s-2004-831224

文献信息

• Synthesis of 1-[2-(Hydroxymethyl)cyclohexyl]pyrimidine Analogues of Nucleosides: A Comparative Study
  作者：Dolores Viña、Lourdes Santana、Eugenio Uriarte、Elías Quezada、Laura Valencia

  DOI：10.1055/s-2004-831224

  日期：——

  carbo-nucleosides analogues of pyrimidine (cyclohexane derivatives) is reported. For the synthesis of the uridine analogue 5a, either construction of the base on the amino group of the amino alcohol 3 or on the amido group of the predecessor β-lactam 1 was more efficient than condensation of the base with a protected diol. The cisconfiguration of 5a was confirmed by X-ray crystallography. Compound 5a was halogenated

  报道了一系列新的嘧啶（环己烷衍生物）的 1,2-二取代碳核苷类似物的合成。对于尿苷类似物 5a 的合成，在氨基醇 3 的氨基上或在前身 β-内酰胺 1 的酰胺基上构建碱基比碱基与受保护的二醇缩合更有效。5a 的顺式构型通过 X 射线晶体学证实。化合物 5a 在尿嘧啶 5 位被 Cl、Br 和 I 卤化。
• Regioselective synthesis of O2- and O6-cyclopyrimidine nucleoside analogues
  作者：Dolores Viña、Elías Quezada、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/j.tet.2006.08.007

  日期：2006.10

  Regioselective synthesis of two new series of cyclonucleoside analogues from the 1,2-carbonucleoside of uracil 1a: O-2 7 '-cyclo-nucleosides (3a-c) and O-6 7 '-cyclonucleosides (4a-c), analogues of pyrimidine (cyclohexane derivatives) is reported. Synthesis Of O-2-cyclo- nucleoside analogues was performed by activation of the hydroxymethyl group of carbocyclic moiety and using the carbonyl group at position 2 of the heterocyclic base as a nucleophile. Synthesis of O-6-cyclonucleoside analogues was achieved by nucleophilic attack of the 7 '-hydroxyl group on the electron-deficient 6-position and subsequently dehydrohalogenation in basic conditions. (c) 2006 Elsevier Ltd. All rights reserved.