1-tosyl-2,3,3a,6,7,7a-hexahydro-1H-indole | 1412894-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-tosyl-2,3,3a,6,7,7a-hexahydro-1H-indole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2,3,3a,6,7,7a-hexahydroindole；1-(4-methylphenyl)sulfonyl-2,3,3a,6,7,7a-hexahydroindole
• CAS: 1412894-95-1
• 化学式: C₁₅H₁₉NO₂S
• 分子量: 277.387
• InChiKey: BISVMDOAHHFVGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-iodoethyl)-N-(cyclohex-2-en-1-yl)-4-methylbenzenesulfonamide 在 二氯二茂钛 、 锰 、 三甲基氯硅烷 、 三苯基膦 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到1-tosyl-2,3,3a,6,7,7a-hexahydro-1H-indole
  参考文献：
  名称：

  Water Control over the Chemoselectivity of a Ti/Ni Multimetallic System: Heck- or Reductive-Type Cyclization Reactions of Alkyl Iodides

  摘要：

  A versatile Ti/Ni multimetallic protocol is described for the efficient catalysis of two different reactions, namely a Heck- and reductive-type cyclization of alkyl iodides, in the absence or presence of water, respectively. Noteworthy, the versatility of Ti(III) chemistry allows an oxidative ending step under reductive conditions to give Heck-type products, and the good H-atom transfer capabilities of Ti(III)-aqua complexes ensure reductive-type cyclizations.

  DOI：

  10.1021/ol3028913

文献信息

• Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis
  作者：Alexander R. O. Venning、Megan R. Kwiatkowski、Joan E. Roque Peña、Brendan C. Lainhart、Akil A. Guruparan、Erik J. Alexanian

  DOI：10.1021/jacs.7b06794

  日期：2017.8.23

  carbocyclization of unactivated alkyl bromides with alkenes is described. This approach uses a commercially available bisphosphine ligand and avoids the use of carbon monoxide atmosphere present in prior studies involving alkyl iodides. Detailed mechanistic studies of the transformation are performed, which are consistent with auto-tandem catalysis involving atom-transfer radical cyclization followed by catalytic

  描述了钯催化未活化烷基溴与烯烃碳环化的通用催化系统的开发。这种方法使用市售的双膦配体，并避免使用先前涉及烷基碘的研究中存在的一氧化碳气氛。对转化进行了详细的机理研究，这与涉及原子转移自由基环化和催化脱卤化氢的自动串联催化一致。这些研究还表明，涉及烷基碘的反应可能通过金属引发而非金属催化的自由基链过程进行。
• Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides
  作者：Megan R. Kwiatkowski、Erik J. Alexanian

  DOI：10.1002/anie.201810757

  日期：2018.12.17

  The development of a general, nickel-catalyzed alkyl-Mizoroki-Heck reaction of unactivated alkyl bromides is described. The mild reaction proceeds efficiently using a wide range of primary and secondary alkyl bromides, and examples of intermolecular cross-couplings are provided. Reaction alkene regioselectivity is significantly enhanced over prior carbocyclizations using palladium catalysis. Mechanistic

  描述了未活化烷基溴的一般镍催化烷基-Mizoroki-Heck 反应的发展。使用各种伯烷基溴和仲烷基溴，温和的反应可以有效进行，并提供了分子间交叉偶联的例子。与之前使用钯催化的碳环化反应相比，反应烯烃区域选择性显着增强。与之前用钯催化观察到的自动串联原子转移环化和卤化物消除相反，机理研究与直接碳环化一致。
• Vitamin B₁₂ and a metal–organic framework enable the photocatalytic generation of alkyl radicals
  作者：Krzysztof R. Dworakowski、Artur Chołuj、Michał J. Chmielewski、Dorota Gryko

  DOI：10.1039/d3cc02941g

  日期：——

  A versatile Co-catalyst-vitamin B12 (cobalamin)-can be photochemically reduced to its catalytically active Co(I) form under visible light irradiation, in the presence of MIL-125-NH2(Ti) as a photocatalyst and utilized for the generation of alkyl radicals. The prior reduction of cobalamin to the Co(II) form is not required in this method.

  一种多功能助催化剂 - 维生素 B 12 （钴胺素） - 在 MIL-125-NH 2 (Ti) 作为光催化剂的情况下，在可见光照射下可以光化学还原为其催化活性 Co( I ) 形式，并用于烷基自由基的产生。该方法不需要预先将钴胺素还原成Co( II )形式。
• Water Control over the Chemoselectivity of a Ti/Ni Multimetallic System: Heck- or Reductive-Type Cyclization Reactions of Alkyl Iodides
  作者：Alba Millán、Luis Álvarez de Cienfuegos、Delia Miguel、Araceli G. Campaña、Juan M. Cuerva

  DOI：10.1021/ol3028913

  日期：2012.12.7

  A versatile Ti/Ni multimetallic protocol is described for the efficient catalysis of two different reactions, namely a Heck- and reductive-type cyclization of alkyl iodides, in the absence or presence of water, respectively. Noteworthy, the versatility of Ti(III) chemistry allows an oxidative ending step under reductive conditions to give Heck-type products, and the good H-atom transfer capabilities of Ti(III)-aqua complexes ensure reductive-type cyclizations.