6-chloro-2-methyl-3-vinylpyridine | 1355205-23-0

• 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: 6-chloro-2-methyl-3-vinylpyridine
• 英文别名: 6-Chloro-2-methyl-3-vinylpyridine；6-chloro-3-ethenyl-2-methylpyridine
• CAS: 1355205-23-0
• 化学式: C₈H₈ClN
• 分子量: 153.611
• InChiKey: QQTMRFUIVVXSMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-2-methyl-3-vinylpyridine 、 二苯基硅烷 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到6-chloro-3-(2-(diphenylsilyl)ethyl)-2-methylpyridine
  参考文献：
  名称：

  Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification

  摘要：

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

  DOI：

  10.1021/ol400977r
• 作为产物：
  描述：

  在 碘 、 sodium methylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.33h， 以69 mg的产率得到6-chloro-2-methyl-3-vinylpyridine
  参考文献：
  名称：

  Single-Pot Access to Bisorganoborinates: Applications in Zweifel Olefination

  摘要：

  Zweifel olefination is a catalyst-free reaction that serves alkene functionalization. While most methods employ commercially available boron pinacol esters, we have assembled a sequence in which the two partners of the formal coupling reaction are installed successively, starting from inexpensive boron alkoxides. The in situ formation of bisorganoborinates was accomplished by consecutive reaction of two different organometallic species. This single-pot procedure represents a great advancement in the generation of organoborinates and their involvement in C-C bond formation.

  DOI：

  10.1021/acs.orglett.9b00493

文献信息

• Tricyclic heterocycles as BET protein inhibitors
  申请人：Incyte Corporation

  公开号：US11091484B2

  公开（公告）日：2021-08-17

  The present invention relates to tricyclic heterocycles which are inhibitors of BET proteins such as BRD2, BRD3, BRD4, and BRD-t and are useful in the treatment of diseases such as cancer.

  本发明涉及三环杂环化合物，它们是 BET 蛋白（如 BRD2、BRD3、BRD4 和 BRD-t）的抑制剂，可用于治疗癌症等疾病。
• Single-Pot Access to Bisorganoborinates: Applications in Zweifel Olefination
  作者：Arif Music、Andreas N. Baumann、Philipp Spieß、Nicolas Hilgert、Martin Köllen、Dorian Didier

  DOI：10.1021/acs.orglett.9b00493

  日期：2019.4.5

  Zweifel olefination is a catalyst-free reaction that serves alkene functionalization. While most methods employ commercially available boron pinacol esters, we have assembled a sequence in which the two partners of the formal coupling reaction are installed successively, starting from inexpensive boron alkoxides. The in situ formation of bisorganoborinates was accomplished by consecutive reaction of two different organometallic species. This single-pot procedure represents a great advancement in the generation of organoborinates and their involvement in C-C bond formation.
• Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification
  作者：Alexey Kuznetsov、Yoshiharu Onishi、Yoshihiro Inamoto、Vladimir Gevorgyan

  DOI：10.1021/ol400977r

  日期：2013.5.17

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.