6-chloro-3a-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one | 115072-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-chloro-3a-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one
• 英文别名: 6-chloro-3a-methyl-3,4-dihydro-2H-pyrrolo[1,2-a]benzimidazol-1-one
• CAS: 115072-98-5
• 化学式: C₁₁H₁₁ClN₂O
• 分子量: 222.674
• InChiKey: UGHLZJRSJACIQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  399.3±42.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  炔丙基脲 、 4-氯-1,2-苯二胺 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 7-chloro-3a-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one 、 6-chloro-3a-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo<1,2-a>benzimidazol-1-one
  参考文献：
  名称：

  Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines

  摘要：

  A process involving gold(I)-catalyzed formal double hydroamination of alkynes, bearing a tethered carboxylic group, for the synthesis of fused dihydrobenzimidazoles and tetrahydroquinazolines has been developed. A series of transition metal catalysts have been screened for this transformation, and a catalyst system consisting of Ph3PAuCl (1 mol %) and AgOTf (1 mol %) was found to be the best. The procedure entails the reaction of easily accessible starting materials such as alkynoic acids and 1,2-diaminobenzenes/2-aminobenzylamines in the presence of the catalyst in 1,2-dichloroethane at 100 degrees C. In the case of alpha-substituted alkynoic acids, the corresponding products were obtained in high diastereoselectivities; the structure of the diastereomers has been unambiguously characterized by NMR techniques. The mechanism of the reaction is discussed, and the origin of the diastereoselectivities is addressed. It was observed that under the microwave irradiation conditions, the reaction time is significantly shortened (0.5 h).

  DOI：

  10.1021/jo1013228

文献信息

• Synthesis and spectroscopic characterizations of both 4b,5-dihydro-4b-methyl-11<i>H</i>-isoindolo[2,1-<i>a</i>]benzimidazol-11-ones and 2,3,3a,4-tetrahydro-3a-methyl-1H-pyrrolo[1,2-<i>a</i>]benzimidazol-1-ones
  作者：Philippe Louvet、FrançOis Thomasson、Cuong Luu-Duc

  DOI：10.1002/jhet.5570310106

  日期：1994.1

  The complete assignment of the 1H and 13C nmr spectra of some derivatives of both 4b,5-dihydro-4b-methyl-11H-isoindolo[2,1-a]benzimidazol-11-one I and 2,3,3a,4-tetrahydro-3a-methyl-1H-pyrrolo[1,2-a]-benzimidazol-1-one II was herein reported by the combined use of one and two-dimensional nmr techniques. Eight compounds, three of which are novel, 2a, 3, 6, were thus prepared. Their uv and ir spectra

  4b，5-dihydro-4b-methyl-11 H -isoindolo [2,1- a ] benzimidazol-11-one I and 2,3,3a的某些衍生物的1 H和13 C nmr光谱的完全分配本文通过一维和二维NMR技术的结合报道了，4-四氢-3a-甲基-1 H-吡咯并[1,2 - a ]-苯并咪唑-1-酮II。由此制备了八种化合物，其中三种是新颖的，即2a，3、6。还获得了它们的紫外光谱和红外光谱。另外，还报道了化合物1、2a，2b，3和6的质谱。
• Chimirri, Alba; Grasso, Silvana; Monforte, Pietro, Heterocycles, 1988, vol. 27, # 1, p. 93 - 100
  作者：Chimirri, Alba、Grasso, Silvana、Monforte, Pietro、Romeo, Giovanni、Zappala, Maria

  DOI：——

  日期：——
• Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Balakrishna Gajula、Balasubramanian Sridhar、Gurava Reddy Pottireddygari、Tadikamalla Prabhakar Rao

  DOI：10.1021/jo1013228

  日期：2010.9.3

  A process involving gold(I)-catalyzed formal double hydroamination of alkynes, bearing a tethered carboxylic group, for the synthesis of fused dihydrobenzimidazoles and tetrahydroquinazolines has been developed. A series of transition metal catalysts have been screened for this transformation, and a catalyst system consisting of Ph3PAuCl (1 mol %) and AgOTf (1 mol %) was found to be the best. The procedure entails the reaction of easily accessible starting materials such as alkynoic acids and 1,2-diaminobenzenes/2-aminobenzylamines in the presence of the catalyst in 1,2-dichloroethane at 100 degrees C. In the case of alpha-substituted alkynoic acids, the corresponding products were obtained in high diastereoselectivities; the structure of the diastereomers has been unambiguously characterized by NMR techniques. The mechanism of the reaction is discussed, and the origin of the diastereoselectivities is addressed. It was observed that under the microwave irradiation conditions, the reaction time is significantly shortened (0.5 h).