dimethyl 2-(1-tosyl-1H-indol-2-yl)cyclopropane-1,1-dicarboxylate | 1150306-55-0

• 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: dimethyl 2-(1-tosyl-1H-indol-2-yl)cyclopropane-1,1-dicarboxylate
• 英文别名: Dimethyl 2-[1-(4-methylphenyl)sulfonylindol-2-yl]cyclopropane-1,1-dicarboxylate；dimethyl 2-[1-(4-methylphenyl)sulfonylindol-2-yl]cyclopropane-1,1-dicarboxylate
• CAS: 1150306-55-0
• 化学式: C₂₂H₂₁NO₆S
• 分子量: 427.478
• InChiKey: ZFNKKKPWAAEPJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)烯丙基-三甲基硅烷 、 dimethyl 2-(1-tosyl-1H-indol-2-yl)cyclopropane-1,1-dicarboxylate 在 四氯化钛 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到dimethyl 2-(4-(chloromethyl)-2-(1-tosyl-1H-indol-2-yl)pent-4-enyl)malonate
  参考文献：
  名称：

  Synthesis of Cyclohexanes via [3 + 3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes

  摘要：

  Lewis acid-assisted ring-opening/allylation of 1,1-cyclopropane diesters, followed by base-mediated ring closure, generates functionalized exo-methylenecyclohexanes in good yield. This two-step procedure is highlighted by expedient preparation of a pyrido[1,2-a]indole skeleton common to the chippiine class of Iboga indole alkaloids.

  DOI：

  10.1021/ol900457z
• 作为产物：
  描述：

  dimethyl 2-((1-tosyl-1H-indol-2-yl)methylene)-malonate 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 15.0h， 以84%的产率得到dimethyl 2-(1-tosyl-1H-indol-2-yl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of Cyclohexanes via [3 + 3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes

  摘要：

  Lewis acid-assisted ring-opening/allylation of 1,1-cyclopropane diesters, followed by base-mediated ring closure, generates functionalized exo-methylenecyclohexanes in good yield. This two-step procedure is highlighted by expedient preparation of a pyrido[1,2-a]indole skeleton common to the chippiine class of Iboga indole alkaloids.

  DOI：

  10.1021/ol900457z

文献信息

• Lewis and Brønsted Acid Induced (3 + 2)-Annulation of Donor–Acceptor Cyclopropanes to Alkynes: Indene Assembly
  作者：Eduard R. Rakhmankulov、Konstantin L. Ivanov、Ekaterina M. Budynina、Olga A. Ivanova、Alexey O. Chagarovskiy、Dmitriy A. Skvortsov、Gennadij V. Latyshev、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1021/ol5037562

  日期：2015.2.20

  (3 + 2)-Annulation of donor-acceptor cyclopropanes to alkynes induced by both Lewis and Bronsted acids has been developed. The reaction provides a rapid approach to functionalized indenes displaying intense visible emission (lambda(max) = 430 nm, Phi = 0.28-0.34).

  供体-受体环丙烷与炔烃之间的（3 + 2）环化反应在路易斯酸和布朗斯特酸的共同诱导下实现。该反应提供了一种快速制备功能化吲哚满的方法，这些吲哚满显示出强烈的可见光发射特性（λmax= 430 nm，Φ= 0.28-0.34）。
• Synthesis of Cyclohexanes via [3 + 3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes
  作者：Katarina Sapeta、Michael A. Kerr

  DOI：10.1021/ol900457z

  日期：2009.5.21

  Lewis acid-assisted ring-opening/allylation of 1,1-cyclopropane diesters, followed by base-mediated ring closure, generates functionalized exo-methylenecyclohexanes in good yield. This two-step procedure is highlighted by expedient preparation of a pyrido[1,2-a]indole skeleton common to the chippiine class of Iboga indole alkaloids.