2-5-chloropyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-5-chloropyridine
• 英文别名: 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine；5-chloro-N,N-bis(trifluoromethanesulfonyl)aminopyridine；N-(5-chloro-2-pyridyl)triflimide；Comins triflimide；N-(6-chloropyridin-2-yl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide
• 化学式: C₇H₃ClF₆N₂O₄S₂
• 分子量: 392.687
• InChiKey: CFXUVIQYZBRSPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 、 2-5-chloropyridine 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到ethyl (Z)-5-phenyl-3-(trifluoromethylsulfonyloxy)pent-2-enoate
  参考文献：
  名称：

  Aromatic farnesyl diphosphate analogues

  摘要：

  A stereocontrolled vinyl triflate-based synthetic route has been used to prepare four analogues of farnesyl diphosphate (FPP) where the terminal isoprene units have been replaced with aromatic moieties. Two of these analogues exhibit no productive interaction with protein farnesyltransferase, but the 2-naphthyl derivative 2 is a modest inhibitor of the enzyme, and the para-biphenyl derivative 4 is a surprisingly effective alternative substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00187-7

文献信息

• High-Pressure Diels−Alder Approach to Natural Kainic Acid
  作者：Sushil K. Pandey、Arturo Orellana、Andrew E. Greene、Jean-François Poisson

  DOI：10.1021/ol062419l

  日期：2006.11.1

  The first Diels-Alder based synthesis of (-)-kainic acid is described. Danishefsky's diene and a vinylogous malonate derived from 4-hydroxyproline combine under high pressure to afford a key bicyclic intermediate with virtually no loss of enantiopurity. This adduct can be converted into the natural product with complete stereocontrol. [reaction: see text].

  描述了第一种基于狄尔斯-阿尔德的（-）-海藻酸合成。Danishefsky的二烯和衍生自4-羟基脯氨酸的乙烯基丙二酸酯在高压下结合，得到了关键的双环中间体，几乎没有对映纯度的损失。该加合物可以通过完全的立体控制转化为天然产物。[反应：请参见文字]。
• Synthesis and biological activity of high-affinity retinoic acid receptor antagonists
  作者：Alan T. Johnson、Liming Wang、Andrew M. Standeven、Maria Escobar、Roshantha A.S. Chandraratna

  DOI：10.1016/s0968-0896(99)00055-3

  日期：1999.7

  This article reports the synthesis and biological activity of new high affinity retinioic acid receptor (RAR) antagonists. The effect of introducing heteroatoms in the bicyclic ring system of the potent dihydronaphthalene RAR antagonist 8, and the variation of the pendant aromatic group on the ability of these compounds to function as RAR antagonists is discussed. The use of binding, transcriptional

  本文报道了新型高亲和力视黄酸受体（RAR）拮抗剂的合成和生物学活性。讨论了在有效的二氢萘RAR拮抗剂8的双环系统中引入杂原子的作用以及芳基侧基的变化对这些化合物充当RAR拮抗剂的能力的影响。结合，转录和体内测定法的使用揭示了2，2-二甲基硫代苯并菲类似物59和2，2-二甲基苯并菲衍生物85在阻断类视色素激动剂诱导的活性中最有效。
• Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine
  作者：Gyoung-Dong Kang、Philip W. Howard、David E. Thurston

  DOI：10.1039/b303274d

  日期：——

  A novel C2-aryl 1,2-unsaturated PBD (14) has been prepared via an enol triflate intermediate (8). The regiochemistry of triflation is dependent upon the point at which the reaction is performed during the synthetic route.

  一种新颖的C2-芳基1,2-不饱和PBD（14）是通过一个烯醇三氟甲磺酸酯中间体（8）制备的。三氟甲磺酸酯化的区域化学取决于在合成路线中进行反应的具体时点。
• Total Synthesis of (±)-Cytisine via the Intramolecular Heck Cyclization of Activated <i>N</i>-Alkyl Glutarimides
  作者：Jotham W. Coe

  DOI：10.1021/ol006765t

  日期：2000.12.1

  [reaction:see text] A synthesis of racemic cytisine 1 has been developed utilizing an intramolecular Heck cyclization to prepare the bridged tricyclic intermediate 2. The cyclization employs activated glutarimide-derived ketene aminals 3 (X = P(O)OEt(2) or SO(2)CF(3)) and represents the first use of such intermediates in metal-catalyzed processes.

  [反应：参见文本]利用分子内Heck环化反应制备了消旋半胱氨酸1的合成，以制备桥接的三环中间体2。环化反应使用了活化的戊二酰亚胺衍生的乙烯酮缩醛3（X = P（O）OEt（2）或SO（2）CF（3）），代表此类中间体在金属催化过程中的首次使用。
• A Ring Expansion Strategy in Antiviral Synthesis: A Novel Approach to TAK‐779
  作者：Terrence L. Smalley

  DOI：10.1081/scc-120037909

  日期：2004.12.31

  Abstract A synthesis of TAK‐779 that relies on construction of a key carboxylic acid intermediate by a ring expansion with TMSCHN2 is described.

  摘要描述了 TAK-779 的合成，该合成依赖于通过 TMSCHN2 扩环来构建关键羧酸中间体。