2-ethyl-3-methyl-2,3-dihydroindole | 50837-62-2

• 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: 2-ethyl-3-methyl-2,3-dihydroindole
• 英文别名: cis-2-ethyl-3-methylindoline；(2S,3S)-2-ethyl-3-methyl-2,3-dihydro-1H-indole
• CAS: 50837-62-2；142612-84-8
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: QXMTXARTSNIIBT-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-methyl-2,3-dihydroindole 在 dirhodium tetraacetate 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 为溶剂， 生成 1-acetyl-4-ethyl-2-hydroxy-5-methyl-4,5-dihydropyrrolo<3,2,1-hi>indole
  参考文献：
  名称：

  Dirhodium tetraacetate catalyzed carbon-hydrogen insertion reaction in N-substituted .alpha.-carbomethoxy-.alpha.-diazoacetanilides and structural analogs. Substituent and conformational effects

  摘要：

  A series of acyclic alpha-carbomethoxy-alpha-diazoacetanilides with different N-substituents, 5a-k, was prepared and the rhodium(II) acetate catalyzed reactions studied. It was found that the rhodium carbenoid reaction with these compounds occurred only at the N-substituent; when the N-substituent is a propargyl group, rhodium carbenoid addition to the triple bond is favored, resulting, ultimately, in the formation of a bicyclic furan derivative 8. With an N-(tert-butyloxycarbonyl)methyl substituent, interception of the rhodium carbenoid by the ester carbonyl oxygen occurred preferentially to give, eventually, 1,4-oxazine derivatives 9 and 9'. For N-alkyl substituents, rhodium carbenoid carbon-hydrogen (C-H) insertion into the alkyl group to give 2-azetidinone and/or 2-pyrrolidinone derivatives was observed. The chemoselectivity of the rhodium carbenoid C-H insertion can be altered by the use of the alpha-acetyl and alpha-phenylsulfonyl substituents. In these cases, exclusive C-H insertion at the N-aryl moiety resulted to give 2(3H)-indolinone products. However, the alpha-substituent effect on the chemoselectivity of the insertion reaction is easily overridden by conformational effects about the amide N-C(O) bond as revealed by the insertion reactions of the conformationally rigid compounds 20a-c. The alpha-substituent effects are reestablished when conformational rigidity is removed, as exemplified by the rhodium carbenoid insertion reactions of compounds 29a,b.

  DOI：

  10.1021/jo00042a018
• 作为产物：
  描述：

  2-乙基-3-甲基-1H-吲哚 在 高氯酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以46%的产率得到2-ethyl-3-methyl-2,3-dihydroindole
  参考文献：
  名称：

  化学酶法立体选择性合成2,3-二取代的吲哚啉非对映异构体

  摘要：

  通过Fischer吲哚化已有效制备了外消旋二氢吲哚，包括各种结构基序，例如C-2和C-3取代（烷基或芳基），顺/反相对立体化学和芳香环（氟，甲基或甲氧基）的官能化以及随后的非保护吲哚的非对映选择性还原。的组合南极假丝酵母脂肪酶A型和烯丙基3-甲氧基苯基碳酸酯已经被鉴定为对他们的动力学拆分最好串联，观察对于大多数所测试的二氢吲哚的优良stereodiscriminations。

  DOI：

  10.1021/jo301307q

文献信息

• Direct Asymmetric Hydrosilylation of Indoles: Combined Lewis Base and Brønsted Acid Activation
  作者：You-Cai Xiao、Chao Wang、Yuan Yao、Jian Sun、Ying-Chun Chen

  DOI：10.1002/anie.201105341

  日期：2011.11.4

  Quite a pair: The first organocatalytic direct asymmetric reduction of unprotected 1H‐indoles to chiral indolines has been developed. The reaction proceeds through the generation of electrophilic indolenium ions by a Brønsted acid, and then chiral Lewis base (1) mediated enantioselective hydride transfer with HSiCl3. A variety of chiral indolines were obtained with moderate to excellent enantioselectivity

  相当一对：已开发出第一个有机催化将未保护的1 H吲哚直接不对称还原为手性二氢吲哚。反应通过布朗斯台德酸生成亲电吲哚离子进行，然后手性Lewis碱（1）与HSiCl 3介导对映选择性氢化物转移。获得各种具有中等至优异对映选择性的手性二氢吲哚。MOM ＝甲氧基甲基。