(+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl
• 英文别名: [8-(7-Pentanoyloxyquinolin-8-yl)quinolin-7-yl] pentanoate
• 化学式: C₂₈H₂₈N₂O₄
• 分子量: 456.541
• InChiKey: LLSCWENTAPZLOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到8-(7-氧代-1H-喹啉-8-基)-1H-喹啉-7-酮
  参考文献：
  名称：

  Enzymatic Resolution of 7,7‘-Dihydroxy-8,8‘- biquinolyl Dipentanoate and Its Conversion to 2,2‘-Di-tert-butyl-7,7‘-dihydroxy-8,8‘-biquinolyl

  摘要：

  [Graphics]Incubation of (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl (4) with a crude cholesterol esterase preparation (from bovine pancreas) yielded highly enantioenriched unreacted dextrorotatory material, (+)-(alpha R)-4 (46%, >= -99% ee), accompanied by the expected diol product, (-)-(alpha S)-7,7'dihydroxy-8,8'-biquinolyl (1), in modest enantiomeric excess (>= 37%, >= 77% ee). Treatment of scalemic diesters 4 with t-BuLi, followed by saponification in the presence of air, gave 2,2'-di-tert-butyl-7,7'-dihydroxy-8,8'-biquinolyl (2) in enantio enriched form. Biquinolyl 2 is less configurationally stable than 1, racemizing rapidly in CHCl3 (t(1/2)(rac) = 1.9 h, rt), and with a moderate rate in MeOH (t(1/2)(rac) = 30.5 h, rt).

  DOI：

  10.1021/jo701611u
• 作为产物：
  描述：

  8-氯喹啉 在 碘苯二乙酸 、 palladium diacetate 、 三苯基膦 、 sodium bromide 、 nickel dichloride 、 锌 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl
  参考文献：
  名称：

  Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C–H Functionalization of 8,8′-Biquinolyl: Emergence of an Atropos from a Tropos State

  摘要：

  7,7'-Dihydroxy-8,8'-biquinolyl(azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8'-biquinolyl mediated by Phl(OAc)(2), and (4) saponification. During the third step, an axially chiral (atropos type) biaryl molecule was directly generated from an essentially achiral (tropos type) biaryl starting material.

  DOI：

  10.1021/ol201539d

文献信息

• OCTAHYDRO BIQUINOLINE COMPOUND
  申请人：Loh Teck Peng

  公开号：US20120088916A1

  公开（公告）日：2012-04-12

  The present invention relates to an octahydro biquinoline compound. Provided is also a method of separating the octahydro biquinoline compound into enantiomers. The octahydro biquinoline compound is of the general formula (V): In formula (V) R 1 is one of H, a protective group and an aliphatic group, with the aliphatic group having a main chain of a length of 1 to about 10 carbon atoms, comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si. R 2 and R 3 are independent from one another selected from the group consisting of (i) H, (ii) one of an aliphatic, an alicyclic, an aromatic, an arylaliphatic, and an arylalicyclic group comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si, an ester, a carbonate group, a carbamoyl group and a phosphate ester. R 4 and R 5 are independent from one another H, an aliphatic, an alicyclic, an aromatic, an arylaliphatic or an arylalicyclic group comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si.

  本发明涉及一种八氢双喹啉化合物。同时提供了将八氢双喹啉化合物分离成对映异构体的方法。所述八氢双喹啉化合物的通式为（V）：在式（V）中，R1是氢、保护基和脂肪基之一，所述脂肪基具有1至约10个碳原子长度的主链，包括0至约6个选自N、O、S、Se和Si的杂原子。R2和R3独立地选自H、一个脂肪基、一个脂环基、一个芳香基、一个芳基脂肪基和一个芳基脂环基，包括0至约6个选自N、O、S、Se和Si的杂原子，以及一个酯基、一个碳酸酯基、一个氨基甲酰基和一个磷酸酯基。R4和R5独立地是H、一个脂肪基、一个脂环基、一个芳香基、一个芳基脂肪基或一个芳基脂环基，包括0至约6个选自N、O、S、Se和Si的杂原子。
• US8691992B2
  申请人：——

  公开号：US8691992B2

  公开（公告）日：2014-04-08
• Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C–H Functionalization of 8,8′-Biquinolyl: Emergence of an <i>Atropos</i> from a <i>Tropos</i> State
  作者：Chao Wang、Darrin M. Flanigan、Lev N. Zakharov、Paul R. Blakemore

  DOI：10.1021/ol201539d

  日期：2011.8.5

  7,7'-Dihydroxy-8,8'-biquinolyl(azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8'-biquinolyl mediated by Phl(OAc)(2), and (4) saponification. During the third step, an axially chiral (atropos type) biaryl molecule was directly generated from an essentially achiral (tropos type) biaryl starting material.
• Enzymatic Resolution of 7,7‘-Dihydroxy-8,8‘- biquinolyl Dipentanoate and Its Conversion to 2,2‘-Di-<i>tert</i>-butyl-7,7‘-dihydroxy-8,8‘-biquinolyl
  作者：Paul R. Blakemore、Selena D. Milicevic、Lev N. Zakharov

  DOI：10.1021/jo701611u

  日期：2007.11.1

  [Graphics]Incubation of (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl (4) with a crude cholesterol esterase preparation (from bovine pancreas) yielded highly enantioenriched unreacted dextrorotatory material, (+)-(alpha R)-4 (46%, >= -99% ee), accompanied by the expected diol product, (-)-(alpha S)-7,7'dihydroxy-8,8'-biquinolyl (1), in modest enantiomeric excess (>= 37%, >= 77% ee). Treatment of scalemic diesters 4 with t-BuLi, followed by saponification in the presence of air, gave 2,2'-di-tert-butyl-7,7'-dihydroxy-8,8'-biquinolyl (2) in enantio enriched form. Biquinolyl 2 is less configurationally stable than 1, racemizing rapidly in CHCl3 (t(1/2)(rac) = 1.9 h, rt), and with a moderate rate in MeOH (t(1/2)(rac) = 30.5 h, rt).