(S)-4-chloronicotine | 919079-42-8

• 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: (S)-4-chloronicotine
• 英文别名: Pyridine, 4-chloro-3-[(2S)-1-methyl-2-pyrrolidinyl]-；4-chloro-3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• CAS: 919079-42-8
• 化学式: C₁₀H₁₃ClN₂
• 分子量: 196.68
• InChiKey: SYOVMUHPOYRFAL-JTQLQIEISA-N

物化性质

• 沸点：
  254.0±40.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-chloronicotine 在 trimethylsilylmethyllithium 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.17h， 以80%的产率得到(S)-4-chloro-5-iodonicotine
  参考文献：
  名称：

  Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine

  摘要：

  The synthesis of novel fused-ring bicyclic (4-6) and tricyclic(7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuo, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.

  DOI：

  10.1021/jo9026929
• 作为产物：
  描述：

  烟碱 在 trimethylsilylmethyllithium 、 六氯乙烷 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.5h， 以91%的产率得到(S)-4-chloronicotine
  参考文献：
  名称：

  TMSCH2Li诱导的（S）-尼古丁区域选择性锂化。

  摘要：

  使用TMSCH2Li作为甲苯中的碱性试剂，已经实现了（S）-尼古丁的第一个区域选择性C-4锂化反应。反应在温和的条件下用少量过量的亲电子试剂进行。随后将4-氯衍生物在相同的碱性试剂下于-78℃下于THF中于C-5进行金属化。该方法为（S）-烟碱化学中的功能多样性提供了直接途径。

  DOI：

  10.1039/b612786j

文献信息

• BIARYL PDE4 INHIBITORS FOR TREATING INFLAMMATORY, CARDIOVASCULAR AND CNS DISORDERS
  申请人：Singh Jasbir

  公开号：US20090324569A1

  公开（公告）日：2009-12-31

  The present invention relates to a genus of biaryl compounds containing at least one further ring. The compounds are PDE4 inhibitors useful for the treatment and prevention of stroke, myocardial infarct and cardiovascular inflammatory diseases and disorders. The compounds have general formula I: A particular embodiment is

  本发明涉及一类含有至少一个进一步环的双芳基化合物。这些化合物是PDE4抑制剂，可用于治疗和预防中风、心肌梗塞和心血管炎症性疾病和障碍。这些化合物具有一般式I：其中，一种特定的实施例为：
• Substituted N-methylene derivatives of thienamycin sulfoxide and sulfone and their preparation
  申请人：Merck & Co., Inc.

  公开号：EP0001264A1

  公开（公告）日：1979-04-04

  Disclosed are substituted N-methylene derivatives of thienamycin sulfoxide (1, n=1) and sulfone (I, n=2) which may be represented by the following structural formula: wherein X and Y are selected from the group consisting of hydrogen, R, OR, SR, and NR' R2 wherein, inter alia, R is substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R1 and R2 are hydrogen or R. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明公开了噻喃霉素亚砜（1，n=1）和砜（I，n=2）的取代 N-亚甲基衍生物，其结构式如下： 其中 X 和 Y 选自由氢、R、OR、SR 和 NR' R2 组成的组，其中除其他外，R 是取代或未取代的：烷基、烯基、炔基、环烷基、环烷基烷基、芳基、芳烷基、杂芳基、杂芳基烷基、杂环烷基和杂环烷基；R1 和 R2 是氢或 R。此类化合物及其药学上可接受的盐、醚、酯和酰胺衍生物可用作抗生素。此外，还公开了制备此类化合物的工艺；包含此类化合物的药物组合物；以及治疗方法，包括在需要抗生素效果时施用此类化合物和组合物。
• O-, N- and carboxyl derivatives of thienamycin sulfoxide and sulfone, their preparation and pharmaceuticals containing said compounds
  申请人：Merck & Co., Inc.

  公开号：EP0001265A1

  公开（公告）日：1979-04-04

  Disclosed are O-, N- and substituted carboxyl derivatives of thienamycin sulfoxide (I, n =1) and thienamycin sulfone (I, n=2): wherein n is 1 or 2; R and R are independently selected from hydrogen and acyl; R is, interalia, hydrogen, acyl or alkyl; X is O or NR; and R is, inter alia, hydrogen or a pharmaceutically acceptable salt or ester moiety. Such derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.

  公开了噻吩霉素亚砜（I，n =1）和噻吩霉素砜（I，n =2）的 O-、N-和取代的羧基衍生物： 其中 n 为 1 或 2；R 和 R 独立选自氢和酰基；R 除其他外为氢、酰基或烷基；X 为 O 或 NR；R 除其他外为氢或药学上可接受的盐或酯分子。此类衍生物可用作抗生素。此外，还公开了制备此类衍生物的工艺、包含此类衍生物的药物组合物以及治疗方法，包括在需要抗生素效果时施用此类衍生物和组合物。
• 6-(1'-Hydroxyethyl)-3-substituted amino-1-azabicyclo(3.2.0)-hept-2-en-7-one-2-carboxylic acid
  申请人：Merck & Co., Inc.

  公开号：EP0134301A1

  公开（公告）日：1985-03-20

  Disclosed are 6-(1'-hydroxyethyl)-3-substituted amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acids (I) : wherein R' and R" are independently selected from H, substituted and unsubstituted alkyl and aralkyl groups, or together form a substituted or unsubstituted cyclic group. Such compounds and their O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds and pharmaceutical compositions comprising such compounds.

  公开了 6-(1'-羟乙基)-3-取代氨基-1-氮杂双环[3.2.0]庚-2-烯-7-酮-2-羧酸 (I) ： 其中，R'和 R "独立地选自 H、取代和未取代的烷基和芳烷基，或共同形成取代或未取代的环状基团。此类化合物及其 O-和羧基衍生物可用作抗生素。还公开了制备此类化合物的工艺和包含此类化合物的药物组合物。
• Biaryl PDE4 inhibitors for treating inflammation
  申请人：Decode Genetics EHF

  公开号：EP2674417A2

  公开（公告）日：2013-12-18

  The present invention relates to a genus of biaryl compounds containing at least one further ring. The compounds are PDE4 inhibitors useful for the treatment and prevention of stroke, myocardial infarct and cardiovascular inflammatory diseases and disorders. The compounds have general formula I:

  本发明涉及一种含有至少一个附加环的双芳基化合物。这些化合物是 PDE4 抑制剂，可用于治疗和预防中风、心肌梗塞和心血管炎症性疾病和紊乱。这些化合物具有通式 I：