[(R)-1-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-3-(3,4-dimethoxyphenyl)propyl]carbamic acid tert-butyl ester | 1345820-59-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: [(R)-1-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-3-(3,4-dimethoxyphenyl)propyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R,2R)-1-[tert-butyl(dimethyl)silyl]oxy-4-(3,4-dimethoxyphenyl)-1-phenylbutan-2-yl]carbamate
• CAS: 1345820-59-8
• 化学式: C₂₉H₄₅NO₅Si
• 分子量: 515.765
• InChiKey: OEQDUTJHKMLNLM-ZEQKJWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(R)-1-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-3-(3,4-dimethoxyphenyl)propyl]carbamic acid tert-butyl ester 在 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 11.5h， 生成 (1R,2R)-N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-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
• 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 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以93%的产率得到[(R)-1-[(R)-(tert-butyldimethylsilanyloxy)(phenyl)methyl]-3-(3,4-dimethoxyphenyl)propyl]carbamic acid tert-butyl ester
  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

• Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine
  作者：Rajesh Malhotra、Amit Ghosh、Rajib Ghosh、Sagar Chakrabarti、Swarup Dutta、Tushar K. Dey、Subho Roy、Sourav Basu、Saumen Hajra

  DOI：10.1016/j.tetasy.2011.08.014

  日期：2011.7

  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.