(S)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one | 182356-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (3S)-3-[4-(4-bromophenyl)phenyl]-3,4-dihydro-2H-naphthalen-1-one
• CAS: 182356-08-7
• 化学式: C₂₂H₁₇BrO
• 分子量: 377.28
• InChiKey: ZBXFXJMMCQYFJR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-羟基香豆素 、 (S)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 作用下， 生成 3R-(4'-bromobiphenyl-4-yl)-1S-(4-hydroxycoumarin-3-yl)-1,2,3,4-tetrahydronaphthalene 、 (3-[(1R,3R)-3-[4-(4-bromophenyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-yl]-4-hydroxychromen-2-one)
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of the Four Diastereomers of Diphenacoum and Brodifacoum

  摘要：

  A highly stereo- and enantio-selective approach to the four stereoisomers of the rodenticides, diphenacoum and brodifacoum, is described. The key step involves the stereospecific formation of one of the crucial bonds in the molecular backbone, and is based on asymmetric organocopper 1,4-addition to chiral imides. Intramolecular cyclization of the resulting butanoate and coupling with 4-hydroxycoumarin, afford the title compounds. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00254-8
• 作为产物：
  描述：

  (4R,5S)-1-[(3S)-3-[4-(4-bromophenyl)phenyl]-4-phenylbutanoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one 在 三氟甲磺酸 作用下， 以 苯 为溶剂， 以79%的产率得到(S)-3-(4'-Bromo-biphenyl-4-yl)-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of the Four Diastereomers of Diphenacoum and Brodifacoum

  摘要：

  A highly stereo- and enantio-selective approach to the four stereoisomers of the rodenticides, diphenacoum and brodifacoum, is described. The key step involves the stereospecific formation of one of the crucial bonds in the molecular backbone, and is based on asymmetric organocopper 1,4-addition to chiral imides. Intramolecular cyclization of the resulting butanoate and coupling with 4-hydroxycoumarin, afford the title compounds. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00254-8

文献信息

• Efficient Asymmetric Synthesis of the Four Diastereomers of Diphenacoum and Brodifacoum
  作者：Pieter S. van Heerden、Barend C.B. Bezuidenhoudt、Daneel Ferreira

  DOI：10.1016/s0040-4020(97)00254-8

  日期：1997.4

  A highly stereo- and enantio-selective approach to the four stereoisomers of the rodenticides, diphenacoum and brodifacoum, is described. The key step involves the stereospecific formation of one of the crucial bonds in the molecular backbone, and is based on asymmetric organocopper 1,4-addition to chiral imides. Intramolecular cyclization of the resulting butanoate and coupling with 4-hydroxycoumarin, afford the title compounds. (C) 1997 Elsevier Science Ltd.