(1R,5R,6R)-1-methyl-2,3-benzobicyclo[3.3.0]oct-2-ene-6-ol | 351355-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,5R,6R)-1-methyl-2,3-benzobicyclo[3.3.0]oct-2-ene-6-ol
• 英文别名: (3R,3aR,8bR)-8b-methyl-2,3,3a,4-tetrahydro-1H-cyclopenta[a]inden-3-ol
• CAS: 351355-72-1
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: LJVAGBVDPVFOQU-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (1R,5R,6R)-1-methyl-2,3-benzobicyclo[3.3.0]oct-2-ene-6-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到
  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：

  (1R,5R,6R)-1-methyl-2,3-benzobicyclo[3.3.0]oct-2-ene-6-yl-2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 在 甲烷磺酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以66%的产率得到(1R,5R,6R)-1-methyl-2,3-benzobicyclo[3.3.0]oct-2-ene-6-ol
  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