trifluoromethanesulfonic acid 2',3'-dihydro-spiro[cyclopent-2-ene-1,3'-[3H]cyclopenta[b]quinoline]-2-yl ester | 1246810-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: trifluoromethanesulfonic acid 2',3'-dihydro-spiro[cyclopent-2-ene-1,3'-[3H]cyclopenta[b]quinoline]-2-yl ester
• 英文别名: Spiro[1,2-dihydrocyclopenta[b]quinoline-3,5'-cyclopentene]-1'-yl trifluoromethanesulfonate
• CAS: 1246810-00-3
• 化学式: C₁₇H₁₄F₃NO₃S
• 分子量: 369.364
• InChiKey: SLSRAYPLQCMQKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 2',3'-dihydro-spiro[cyclopent-2-ene-1,3'-[3H]cyclopenta[b]quinoline]-2-yl ester 、 Diphenylphosphine oxide 在 palladium diacetate 、 N,N-二异丙基乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以85%的产率得到2',3'-dihydro-2-diphenylphosphinylspiro[cyclopent-2-ene-1,3'-[3H]cyclopenta[b]quinoline]
  参考文献：
  名称：

  Synthesis of a new type of P,N-ligand with a spiro skeleton for Ir-catalyzed asymmetric hydrogenations

  摘要：

  A new type of chiral phosphine-quinoline ligand bearing a spiro[4,4]-1,6-nonadiene scaffold was designed and synthesized. Its cationic iridium complex has been characterized by X-ray diffraction analysis and evaluated in the catalytic asymmetric hydrogenation of alkene and imine derivatives, giving the corresponding hydrogenation products with high activity albeit moderate enantioselecitivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.022
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 2',3'-dihydro-1-oxo-spiro[cyclopentane-2,3'-[3H]cyclopenta[b]quinoline] 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.33h， 以96%的产率得到trifluoromethanesulfonic acid 2',3'-dihydro-spiro[cyclopent-2-ene-1,3'-[3H]cyclopenta[b]quinoline]-2-yl ester
  参考文献：
  名称：

  Synthesis of a new type of P,N-ligand with a spiro skeleton for Ir-catalyzed asymmetric hydrogenations

  摘要：

  A new type of chiral phosphine-quinoline ligand bearing a spiro[4,4]-1,6-nonadiene scaffold was designed and synthesized. Its cationic iridium complex has been characterized by X-ray diffraction analysis and evaluated in the catalytic asymmetric hydrogenation of alkene and imine derivatives, giving the corresponding hydrogenation products with high activity albeit moderate enantioselecitivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.022