4,4-dimethyl-1,2,3,4-tetrahydrocarbazole | 666738-15-4

• 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: 4,4-dimethyl-1,2,3,4-tetrahydrocarbazole
• 英文别名: 4,4-Dimethyl-1,2,3,9-tetrahydrocarbazole
• CAS: 666738-15-4
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: IWIGBZPGMCNTMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-1,2,3,4-tetrahydrocarbazole 在 sodium acetate 、 sodium hydride 作用下， 以 乙醇 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 58.0h， 生成
  参考文献：
  名称：

  The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

  摘要：

  To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl- 1,2,3,4,-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.

  DOI：

  10.3987/com-03-s22
• 作为产物：
  描述：

  4,4-dimethyl-1,2,3,4-tetrahydrocarbazol-1-one 在 氢氧化钾 、 一水合肼 作用下， 以 三乙二醇 为溶剂， 反应 4.0h， 以38%的产率得到4,4-dimethyl-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  The Vilsmeier-Haack Reaction on Methyl Homologues of N-Benzyltetrahydrocarbazole (Synthetic Studies on Indoles 52)

  摘要：

  To examine the steric effect in the Vilsmeier-Haack reaction of N-benzyl- 1,2,3,4,-tetrahydrocarbazole (1), the reactions were carried out on three methyl homologues of 1. It was found that 1-methyl- or 4,4-dimethyl group has a large effect on reactivity due to their steric bulkiness. This result shows the importance of an initial attack at the 4a-position for the formation of these products.

  DOI：

  10.3987/com-03-s22

文献信息

• Lewis Acid-Catalyzed Carbofunctionalization of Uncommon <i>C</i>,<i>N</i>-Diacyliminium Ions: Controlling Regio- and Enantioselectivity
  作者：Lisa Marie Gronbach、Alice Voss、Mario Frahm、Alexander Villinger、Jonas Bresien、Dirk Michalik、Malte Brasholz

  DOI：10.1021/acs.orglett.1c02857

  日期：2021.10.15

  precursors to novel and uncommon cyclic C,N-diacyliminium ions 3. We report here the first Lewis acid-catalyzed C–C bond forming reactions of these species with TMSCN and silyl enol ethers as nucleophiles and utilizing TIPSOTf as well as Sc(OTf)3 as catalysts. Employing Sc(OTf)3/pybox complexes as a chiral catalyst system, regio- and enantioselective asymmetric alkylations with silyl enol ethers were achieved

  三环氮杂 [1,2- a ] 吲哚乙酸盐7可通过环庚烷 [ b ] 吲哚1的可见光驱动催化光氧化轻松获得，是新颖和不常见的环状C、N-二酰基亚胺离子3 的方便前体。我们在此报告了这些物种与 TMSCN 和甲硅烷基烯醇醚作为亲核试剂并利用 TIPSOTf 以及 Sc(OTf) 3作为催化剂的首次路易斯酸催化 C-C 键形成反应。使用 Sc(OTf) 3 /pybox 配合物作为手性催化剂体系，实现了与甲硅烷基烯醇醚的区域选择性和对映选择性不对称烷基化。