(R)-13-[2-(3,4-dimethoxyphenyl)ethyl]-8,9,12,13,14,15,17,18-octahydro-11H-dinaphtho[1,2-p:1,2-n][1,4,10,13,7]tetraoxazacycloheptadecine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-13-[2-(3,4-dimethoxyphenyl)ethyl]-8,9,12,13,14,15,17,18-octahydro-11H-dinaphtho[1,2-p:1,2-n][1,4,10,13,7]tetraoxazacycloheptadecine
• 英文别名: 18-[2-(3,4-Dimethoxyphenyl)ethyl]-12,15,21,24-tetraoxa-18-azapentacyclo[23.8.0.02,11.03,8.028,33]tritriaconta-1(25),2(11),3,5,7,9,26,28,30,32-decaene
• 化学式: C₃₈H₄₁NO₆
• 分子量: 607.747
• InChiKey: UGJIYKJTVXZBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-2,2'-bis[2-(2-iodoethoxy)ethoxy]-1,1'-binaphthyl 、 3,4-二甲氧基苯乙胺 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以13%的产率得到(R)-13-[2-(3,4-dimethoxyphenyl)ethyl]-8,9,12,13,14,15,17,18-octahydro-11H-dinaphtho[1,2-p:1,2-n][1,4,10,13,7]tetraoxazacycloheptadecine
  参考文献：
  名称：

  BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of α-aminophosphonates

  摘要：

  Several novel 1.1'-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.002
• 作为试剂：
  描述：

  diethyl (((diphenylmethylene)amino)methyl)phosphonate 、 甲基丙烯腈 在 (R)-13-[2-(3,4-dimethoxyphenyl)ethyl]-8,9,12,13,14,15,17,18-octahydro-11H-dinaphtho[1,2-p:1,2-n][1,4,10,13,7]tetraoxazacycloheptadecine 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 [1S-(benzhydrylidene-amino)-3R-cyano-3-methyl-propyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of α-aminophosphonates

  摘要：

  Several novel 1.1'-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.002

文献信息

• BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of α-aminophosphonates
  作者：Truong Son Pham、János B. Czirok、László Balázs、Krisztina Pál、Miklós Kubinyi、István Bitter、Zsuzsa Jászay

  DOI：10.1016/j.tetasy.2011.02.002

  日期：2011.2

  Several novel 1.1'-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra. (C) 2011 Elsevier Ltd. All rights reserved.