2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one | 109000-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one
• 英文别名: 2-(4-Methylbenzene-1-sulfonyl)-2-azabicyclo[2.2.1]hept-5-en-3-one；2-(4-methylphenyl)sulfonyl-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 109000-07-9
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: LXJWTEPJMYAFKP-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±55.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以62%的产率得到cis-4-p-toluenesulfonylaminocyclopent-2-enylmethanol
  参考文献：
  名称：

  Synthesis of Nucleosides and Related Compounds. Part XX. Synthesis of Carbocyclic Nucleosides from 2-Azabicyclo(2.2.1)hept-5-en-3-ones: Sodium Borohydride-Mediated Carbon-Nitrogen Bond Cleavage of Five-and Six-Membered Lactams.

  摘要：

  通过利用硼氢化钠介导的C-N键断裂作为关键步骤，从2-氮杂双环[2.2.1]庚-5-烯-3-酮出发，经过少量步骤，立体选择性地合成了多种碳环核糖呋喃糖苷核苷。新型合成前体(±)-4β-羟甲基-1β-脲基环戊烷-2α, 3α-二醇[(±)-碳环核糖呋喃糖苷脲]的易得性，不仅提供了通往碳环核糖呋喃糖苷嘧啶的便捷途径，还提供了另一种途径，即合成相应的环戊胺，(±)-1β-氨基-4β-羟甲基环戊烷-2α, 3α-二醇[(±)-碳环核糖呋喃糖苷胺]，这对于相应嘌呤核苷的合成非常有用。

  DOI：

  10.1248/cpb.39.1112
• 作为产物：
  描述：

  环戊二烯 在 oxonium 、 sodium hydride 作用下， 生成 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one
  参考文献：
  名称：

  .pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir

  摘要：

  Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford pi-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (+/-)-carbovir,(1) from cyclopentadiene in only seven steps and 13% overall yield.

  DOI：

  10.1021/jo00096a006

文献信息

• Synthesis of Nucleosides and Related Compounds. Part XX. Synthesis of Carbocyclic Nucleosides from 2-Azabicyclo(2.2.1)hept-5-en-3-ones: Sodium Borohydride-Mediated Carbon-Nitrogen Bond Cleavage of Five-and Six-Membered Lactams.
  作者：Nobuya KATAGIRI、Makoto MUTO、Masahiro NOMURA、Tohru HIGASHIKAWA、Chikara KANEKO

  DOI：10.1248/cpb.39.1112

  日期：——

  Various carbocyclic ribofuranosyl nucleosides were stereoselectively synthesized through a small number of steps from 2-azabicyclo[2.2.1]hept-5-en-3-ones by the use of sodium borohydride-mediated C-N bond cleavage as a key step. Ready availability of a novel synthetic precursor, (±)-4β-hydroxymethyl-1β-ureidocyclopentane-2α, 3α-diol [(±)-carbocyclic ribofuranosylurea], provides not only facile routes to carbocyclic robofuranosylpyrimidines, but also another route to the corresponding cyclopentylamine, (±)-1β-amino-4β-hydroxymethylcyclopentane-2α, 3α-diol [(±)-carbocyclic ribofuranosylamine], which is useful for the synthesis of the corresponding purine nucleosides.

  通过利用硼氢化钠介导的C-N键断裂作为关键步骤，从2-氮杂双环[2.2.1]庚-5-烯-3-酮出发，经过少量步骤，立体选择性地合成了多种碳环核糖呋喃糖苷核苷。新型合成前体(±)-4β-羟甲基-1β-脲基环戊烷-2α, 3α-二醇[(±)-碳环核糖呋喃糖苷脲]的易得性，不仅提供了通往碳环核糖呋喃糖苷嘧啶的便捷途径，还提供了另一种途径，即合成相应的环戊胺，(±)-1β-氨基-4β-羟甲基环戊烷-2α, 3α-二醇[(±)-碳环核糖呋喃糖苷胺]，这对于相应嘌呤核苷的合成非常有用。
• Stereospecific synthesis of carbocyclic nucleosides from 2-azabicyclo-[2.2.1]heptan-3-ones via sodium borohydride mediated carbon-nitrogen bond cleavage
  作者：Nobuya Katagiri、Makoto Muto、Chikara Kaneko

  DOI：10.1016/s0040-4039(00)99542-x

  日期：1989.1

  synthesized from 2-azabicyclo[2.2.1]hept-5-en-3-one readily available from cyclopentadiene, through introduction of an electron-withdrawing substituent at the 2-position followed by reduction with sodium borohydride.

  通过从2-戊二烯[2.2.1]庚-5-烯-3-酮（可从环戊二烯容易获得）合成新的碳环核苷合成子，方法是在2-位引入吸电子取代基，然后用硼氢化钠还原。
• Cyclopentenecarboxamide derivative, method for preparing the same and bicycloamide derivative used therein
  申请人：KURARAY CO., LTD.

  公开号：EP0775705A2

  公开（公告）日：1997-05-28

  A cyclopentenecarboxamide derivative represented by the formula (I): and a method for preparing the cyclopentencarboxamide derivative. A bicycloamide derivative represented by the formula (II): and a method for preparing the bicycloamide derivative.

  一种由式(I)代表的环戊烯甲酰胺衍生物： 以及制备该环戊烯甲酰胺衍生物的方法。一种由式（II）代表的双环酰胺衍生物： 以及制备该双环酰胺衍生物的方法。
• Bicycloamide derivatives
  申请人：Kuraray Co., Ltd.

  公开号：EP1394163A1

  公开（公告）日：2004-03-03

  Bicycloamide derivatives represented by the formulae (II-1), (II-2) and (II-3) wherein R2, R3, R4 and R5 have the meanings given in the claims are useful intermediates for preparing carbocyclic nucleosides.

  式 (II-1)、(II-2) 和 (II-3) 所代表的双环酰胺衍生物 其中 R2、R3、R4 和 R5 具有权利要求中给出的含义，是制备碳环核苷的有用中间体。
• Palmer, Christopher F.; Parry, Keith P.; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 1021 - 1028
  作者：Palmer, Christopher F.、Parry, Keith P.、Roberts, Stanley M.、Sik, Vladimir

  DOI：——

  日期：——