(1R,3R)-1,3-bis(1-bromo-2-naphthoxy)-1,3-diphenylpropane | 188955-95-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R,3R)-1,3-bis(1-bromo-2-naphthoxy)-1,3-diphenylpropane
• 英文别名: 1-bromo-2-[(1R,3R)-3-(1-bromonaphthalen-2-yl)oxy-1,3-diphenylpropoxy]naphthalene
• CAS: 188955-95-5
• 化学式: C₃₅H₂₆Br₂O₂
• 分子量: 638.398
• InChiKey: OYCWKNZLWPHEQA-CZNDPXEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3R)-1,3-bis(1-bromo-2-naphthoxy)-1,3-diphenylpropane 在 正丁基锂 、 氧气 作用下， 生成 (13R,15R)-13,15-diphenyl-12,16-dioxapentacyclo[15.8.0.02,11.03,8.020,25]pentacosa-1(17),2(11),3,5,7,9,18,20,22,24-decaene
  参考文献：
  名称：

  Axial chirality control by 2,4-pentanediol or its analogue as a simple chiral linking bridge. Highly diastereodifferentiating homocoupling of a 1-lithio-2-naphthyl ether

  摘要：

  Diastereodifferentiating oxidative homocoupling of 1-lithio-2-naphthyl ether linked by optically active 2,4-pentanediol or 1,3-diphenyl-1,3-propanediol gave 2,2'-binaphthyl ether of over 99% diastereomeric excess. By elimination of the chiral auxiliary from the product, enantiomerically pure binaphthol was obtained in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00022-0
• 作为产物：
  描述：

  1-溴-2-萘酚 、 (1S,3S)-1,3-diphenylpropane-1,3-diol 在 三丁基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以84.8%的产率得到(1R,3R)-1,3-bis(1-bromo-2-naphthoxy)-1,3-diphenylpropane
  参考文献：
  名称：

  Axial chirality control by 2,4-pentanediol or its analogue as a simple chiral linking bridge. Highly diastereodifferentiating homocoupling of a 1-lithio-2-naphthyl ether

  摘要：

  Diastereodifferentiating oxidative homocoupling of 1-lithio-2-naphthyl ether linked by optically active 2,4-pentanediol or 1,3-diphenyl-1,3-propanediol gave 2,2'-binaphthyl ether of over 99% diastereomeric excess. By elimination of the chiral auxiliary from the product, enantiomerically pure binaphthol was obtained in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00022-0

文献信息

• Axial chirality control by 2,4-pentanediol or its analogue as a simple chiral linking bridge. Highly diastereodifferentiating homocoupling of a 1-lithio-2-naphthyl ether
  作者：Takashi Sugimura、Hideyuki Yamada、Shintaro Inoue、Akira Tai

  DOI：10.1016/s0957-4166(97)00022-0

  日期：1997.2

  Diastereodifferentiating oxidative homocoupling of 1-lithio-2-naphthyl ether linked by optically active 2,4-pentanediol or 1,3-diphenyl-1,3-propanediol gave 2,2'-binaphthyl ether of over 99% diastereomeric excess. By elimination of the chiral auxiliary from the product, enantiomerically pure binaphthol was obtained in good yield. (C) 1997 Elsevier Science Ltd.