(1S,2R)-(-)-2-ethyl-5,8-dimethyl-1,2-dihydronaphth-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R)-(-)-2-ethyl-5,8-dimethyl-1,2-dihydronaphth-1-ol
• 英文别名: (-)-(1S,2R)-2-ethyl-5,8-dimethyl-1,2-dihydro-1-naphthol；(1S,2R)-2-ethyl-5,8-dimethyl-1,2-dihydronaphthalen-1-ol
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: ANXKMZQJKWJSSJ-RISCZKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  diethylzinc 、 5,8-dimethyl-1,4-epoxy-1,4-dihydronaphthalene 在 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以90%的产率得到(1S,2R)-(-)-2-ethyl-5,8-dimethyl-1,2-dihydronaphth-1-ol
  参考文献：
  名称：

  Copper Phosphoramidite Catalyzed Enantioselective Ring-Opening of Oxabicyclic Alkenes:  Remarkable Reversal of Stereocontrol

  摘要：

  [GRAPHICS]An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of ant stereoselectlvity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).

  DOI：

  10.1021/ol026220u

文献信息

• Copper-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Grignard Reagents
  作者：Wei Zhang、Li-Xin Wang、Wen-Jian Shi、Qi-Lin Zhou

  DOI：10.1021/jo050015l

  日期：2005.4.1

  Simple Grignard reagents were applied in copper-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadiene derivatives using spiro phosphoramidite ligands. Excellent anti-stereoselectivities and good enantioselectivities were achieved.

  使用螺旋亚磷酰胺配体，将简单的格氏试剂用于铜催化的草酰苯并降冰片二烯衍生物的不对称开环反应中。获得了优异的抗立体选择性和良好的对映选择性。
• Copper Phosphoramidite Catalyzed Enantioselective Ring-Opening of Oxabicyclic Alkenes:  Remarkable Reversal of Stereocontrol
  作者：Fabio Bertozzi、Mauro Pineschi、Franco Macchia、Leggy A. Arnold、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/ol026220u

  日期：2002.8.1

  [GRAPHICS]An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of ant stereoselectlvity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).