3-(1-Methylinden-1-yl)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate | 351355-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-(1-Methylinden-1-yl)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 351355-19-6
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: JIBJFBANEAERMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-Methylinden-1-yl)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 吡啶 、 甲烷磺酸 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 53.5h， 生成
  参考文献：
  名称：

  Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via (−)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation

  摘要：

  By treatment of the racemic 3-(indenyl)alkyl carbamate rac-8 with sec-BuLi-(-)-sparteine, cyclocarbolithiation occurs, which is accompanied by kinetic resolution during the cyclisation step. After addition of electrophiles, the stereohomogeneous optically active benzobicyclo[3.3.0]octenols of type 13 are obtained. Increasing the temperature from - 78 to - 40 degreesC or the application of TMEDA instead of (-)-sparteine yields the formation of the tricyclic cyclopropane 14. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00832-9
• 作为产物：
  描述：

  (3-hydroxypropyl) 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 吡啶 、 正丁基锂 、 鹰爪豆碱 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(1-Methylinden-1-yl)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via (−)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation

  摘要：

  By treatment of the racemic 3-(indenyl)alkyl carbamate rac-8 with sec-BuLi-(-)-sparteine, cyclocarbolithiation occurs, which is accompanied by kinetic resolution during the cyclisation step. After addition of electrophiles, the stereohomogeneous optically active benzobicyclo[3.3.0]octenols of type 13 are obtained. Increasing the temperature from - 78 to - 40 degreesC or the application of TMEDA instead of (-)-sparteine yields the formation of the tricyclic cyclopropane 14. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00832-9

文献信息

• Synthesis of enantioenriched indene-derived bicyclic alcohols and tricyclic cyclopropanes via (−)-sparteine-mediated lithiation of a racemic precursor and kinetic resolution during the cyclocarbolithiation
  作者：H. Laqua、R. Fröhlich、B. Wibbeling、D. Hoppe

  DOI：10.1016/s0022-328x(00)00832-9

  日期：2001.4

  By treatment of the racemic 3-(indenyl)alkyl carbamate rac-8 with sec-BuLi-(-)-sparteine, cyclocarbolithiation occurs, which is accompanied by kinetic resolution during the cyclisation step. After addition of electrophiles, the stereohomogeneous optically active benzobicyclo[3.3.0]octenols of type 13 are obtained. Increasing the temperature from - 78 to - 40 degreesC or the application of TMEDA instead of (-)-sparteine yields the formation of the tricyclic cyclopropane 14. (C) 2001 Elsevier Science B.V. All rights reserved.