6-chloro-3-(3-methylpent-3-en-1-yl)-1H-indole | 596105-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-chloro-3-(3-methylpent-3-en-1-yl)-1H-indole
• 英文别名: 6-chloro-3-(3-methylpent-3-enyl)-1H-indole
• CAS: 596105-57-6
• 化学式: C₁₄H₁₆ClN
• 分子量: 233.741
• InChiKey: AZLLQZRTSRMTFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  6-chloro-3-(3-methylpent-3-en-1-yl)-1H-indole 在 palladium diacetate 烟酸乙酯 、 氧气 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 2-甲基-2-丁醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 33.75h， 生成 6-Chloro-3,4-dimethyl-3-vinyl-1,2,3,4-tetrahydro-cyclopenta[b]indole
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y
• 作为产物：
  描述：

  6-氯吲哚 在 indium(III) chloride 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 6-chloro-3-(3-methylpent-3-en-1-yl)-1H-indole
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y

文献信息

• Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(<scp>ii</scp>)–SPRIX-catalyzed C–H activation
  作者：Mohamed Ahmed Abozeid、Shiho Sairenji、Shinobu Takizawa、Makoto Fujita、Hiroaki Sasai

  DOI：10.1039/c7cc03199h

  日期：——

  conjunction with the chiral spiro bis(isoxazoline) ligand (SPRIX). The presence of an N-allyl substituent on the substrate has a strong impact on both reactivity and selectivity, leading to tricyclic indole products (up to 96% ee) with a chiral quaternary carbon center.

  通过Pd（OCOCF 3）2和手性螺双（异恶唑啉）配体（SPRIX）建立了通过C–H活化的3-烯基吲哚的高对映选择性环化反应。底物上N-烯丙基取代基的存在对反应性和选择性都有很强的影响，导致具有手性季碳中心的三环吲哚产物（至多96％ee）。