(1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitro-benzenesulfonamide | 1315338-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitro-benzenesulfonamide
• 英文别名: (1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-nitrobenzenesulfonamide；N-((1R,2R)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-nitrobenzenesulfonamide；N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitrobenzenesulfonamide；N-[(1R,2R)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitrobenzenesulfonamide
• CAS: 1315338-44-3
• 化学式: C₂₄H₂₄N₂O₆S
• 分子量: 468.53
• InChiKey: AIWYNWWYIMSZGM-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitro-benzenesulfonamide 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (6aR,12bS)-10,11-dimethoxy-6-(4-nitrobenzenesulfonyl)-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine
  参考文献：
  名称：

  Asymmetric synthesis of the dopamine D1 agonist, dihydrexidine

  摘要：

  A concise asymmetric synthesis of first, high affinity domaine D1 full agonist, dihydrexidine has been accomplished via catalytic enantioselective aziridination and subsequent one-pot Friedel-Crafts cyclization of an in situ generated tethered aziridine with high diastereo- and enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.008
• 作为产物：
  描述：

  [(R)-1-[(R)-(tert-butyldimethylsilanyloxy)phenylmethyl]-3-(3,4-dimethoxyphenyl)allyl]carbamic acid tert-butyl ester 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 9.5h， 生成 (1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-nitro-benzenesulfonamide
  参考文献：
  名称：

  Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine

  摘要：

  A scalable asymmetric synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin 2 and its N-nosyl derivative 12 have been achieved from Garner aldehyde derived from easily available D-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel-Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin 12. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.014

文献信息

• Rhodium‐Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Dihydronitronaphthalenes
  作者：Saumen Hajra、Rajib Ghosh、Sagar Chakrabarti、Amit Ghosh、Swarup Dutta、Tushar K. Dey、Rajesh Malhotra、Sonika Asijaa、Subho Roy、Shantanu Dutta、Sourav Basu

  DOI：10.1002/adsc.201200241

  日期：2012.9.17

  A highly enantioselective (up to 91% ee) rhodium‐catalyzed asymmetric addition of arylboronic acids has been achieved leading to the challenging dihydro‐3‐nitronaphthalenes using one equivalent of phosphoramidite ligand to rhodium catalyst. A concise formal asymmetric synthesis of the dopamine D1 agonist, dihydrexidine was accomplished using the method.

  已经实现了高对映选择性（高达91％ee）的铑催化芳基硼酸的不对称加成反应，导致使用一当量的亚磷酰胺配体与铑催化剂形成具有挑战性的二氢-3-硝基萘。使用该方法完成了多巴胺D1激动剂二氢己定的简明形式不对称合成。
• Divergent asymmetric synthesis of hexahydrobenzophenanthridine dopamine D1 agonists, A-86929, and dihydrexidine
  作者：Rajesh Malhotra、Sagar Chakrabarti、Amit Ghosh、Rajib Ghosh、Tushar K. Dey、Swarup Dutta、Shantanu Dutta、Subho Roy、Sourav Basu、Saumen Hajra

  DOI：10.1016/j.tetasy.2013.02.003

  日期：2013.3

  A divergent and scalable asymmetric synthesis of the dopamine D1 agonists, A-86929, and dihydrexidine with high diastereo- and enantioselectivity was accomplished from Weinreb amide 8 derived from inexpensive and easily available L-serine. The synthesis of A-86929 involves only one chromatographic purification. (C) 2013 Elsevier Ltd. All rights reserved.