{2-[(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalen-1-yl]phenyl}methanol | 675872-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: {2-[(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalen-1-yl]phenyl}methanol
• 英文别名: {2-[(1S,2R)-6,7-dimethoxy-2-nitro-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl}methanol；[2-[(1S,2R)-6,7-dimethoxy-2-nitro-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]methanol
• CAS: 675872-24-9
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: ROADLVVVWSFMIN-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {2-[(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalen-1-yl]phenyl}methanol 在 盐酸 、 potassium carbonate 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 叔丁醇 为溶剂， 反应 3.67h， 生成 trans-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine
  参考文献：
  名称：

  Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene

  摘要：

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.039
• 作为产物：
  描述：

  1-bromo-2-trityloxymethylbenzene 在 盐酸 、 正丁基锂 、 (1S,2S)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 23.0h， 生成 {2-[(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalen-1-yl]phenyl}methanol
  参考文献：
  名称：

  Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene

  摘要：

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.039

文献信息

• Construction of Arene-Fused-Piperidine Motifs by Asymmetric Addition of 2-Trityloxymethylaryllithiums to Nitroalkenes:  The Asymmetric Synthesis of a Dopamine D1 Full Agonist, A-86929
  作者：Mitsuaki Yamashita、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1021/ja031760n

  日期：2004.2.1

  The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process was highlighted by the first asymmetric synthesis of a dopamine D1 full agonist, A-86929.
• Tetrahedron 2004, 60, 4237-4242
  作者：

  DOI：——

  日期：——
• Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene
  作者：Mitsuaki Yamashita、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2004.03.039

  日期：2004.5

  Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type cyclization, which were the drawback of the previously reported synthesis involving asymmetric conjugate addition of phenyllithium to an enoate, was realized by the newly developed asymmetric reaction. Short and efficient synthetic way gave optically pure dihydrexidine in 45% overall yield via eight steps. Improved synthesis of the best chiral ligand 13 was realized under the Buchwald conditions. (C) 2004 Elsevier Ltd. All rights reserved.