(2R-trans)-(2-Naphthalenyl) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxylate | 134915-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R-trans)-(2-Naphthalenyl) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxylate
• 英文别名: (2R-trans)-(2-naphthalenyl) 3-[2(8-phenyloctyl)phenyl]oxiranecarboxylate；(2R-trans)-(2-naphthalenyl) 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate；naphthalen-2-yl (2R,3S)-3-[2-(8-phenyloctyl)phenyl]oxirane-2-carboxylate
• CAS: 134915-57-4
• 化学式: C₃₃H₃₄O₃
• 分子量: 478.631
• InChiKey: QDHBJSHCQYEIOJ-AJQTZOPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R-trans)-(2-Naphthalenyl) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxylate 在 ammonium hydroxide 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以87%的产率得到(2R)-trans-(+) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxamide
  参考文献：
  名称：

  A practical, enantioselective synthesis of SK&F 104353

  摘要：

  A highly efficient and enantioselective (>99.5% ee) synthesis of the title compound has been accomplished. Key steps include (1) epoxidation of unsaturated ketone 7 in the presence of a polyamino acid to afford compound 8 in >95% ee, (2) regioselective Baeyer-Villiger rearrangement of epoxy ketone 8 to afford glycidic ester 9, and (3) regioselective (35:1) opening of lithium glycidate 13 at C-3 with methyl 3-mercaptopropionate. The approach is economical, and all transformations proceed in high yield and are amenable to large-scale preparation.

  DOI：

  10.1021/jo00075a019
• 作为产物：
  描述：

  (2R-trans)-(2-Naphthalenyl) <3-<2-(8-phenyloctyl)phenyl>oxiranyl>methanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 生成 (2R-trans)-(2-Naphthalenyl) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxylate
  参考文献：
  名称：

  Process for preparation of epoxy esters and intermediates prepared

  摘要：

  本发明涉及一种制备环氧酯的过程，以及通过这种过程制备的中间体，特别是一种生产非外消旋环氧酯的过程，这种环氧酯在制备药物化合物的中间体中有用。

  公开号：

  US05110959A1

文献信息

• Process and intermediate for the preparation of
  申请人：SmithKline Beecham Corporation

  公开号：US05693857A1

  公开（公告）日：1997-12-02

  ##STR1## This invention relates to intermediate compounds of formula (VI), wherein: R.sub.1 is (L).sub.a --(CH.sub.2).sub.b --(T).sub.c --B; a is 0 or 1; b is 3 to 14; c is 0 or 1; L and T are independently sulfur, oxygen, CH.dbd.CH, C.tbd.C, or CH.sub.2 ; B is H, C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl unsubstituted or monosubstituted by Br, Cl, CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, methylthio or trifluoromethylthio; R.sub.2 and A are independently selected from H, CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, F, Cl, Br, I, OH, NO.sub.2 or NH.sub.2 ; or, when R.sub.1 and A are H, R.sub.2 is (L).sub.a --(CH.sub.2).sub.b --(T).sub.c --B wherein a, b, c, L, T and B are as defined above; and M is H, Li, Na, K, NH.sub.4 or an organic ammonium cation, and their use in a process for preparing leukotriene antagonists.

  本发明涉及公式（VI）的中间化合物，其中：R.sub.1是（L）.sub.a --（CH.sub.2）.sub.b --（T）.sub.c --B；a为0或1；b为3至14；c为0或1；L和T分别为硫、氧、CH.dbd.CH、C.tbd.C或CH.sub.2；B为H、C.sub.1-4烷基、乙炔基、三氟甲基、异丙烯基、呋喃基、噻吩基、环己基或苯基，未取代或经Br、Cl、CF.sub.3、C.sub.1-4烷氧基、C.sub.1-4烷基、甲硫氧基或三氟甲基硫氧基单取代；R.sub.2和A分别选自H、CF.sub.3、C.sub.1-4烷基、C.sub.1-4烷氧基、F、Cl、Br、I、OH、NO.sub.2或NH.sub.2；或当R.sub.1和A为H时，R.sub.2为（L）.sub.a --（CH.sub.2）.sub.b --（T）.sub.c --B，其中a、b、c、L、T和B如上定义；M为H、Li、Na、K、NH.sub.4或有机铵阳离子，并且它们在制备白三烯拮抗剂的过程中的用途。
• Process for preparation of epoxy esters and intermediates prepared
  申请人：Smithkline Beckman Corp.

  公开号：US05110959A1

  公开（公告）日：1992-05-05

  This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.

  本发明涉及一种制备环氧酯的过程，以及通过这种过程制备的中间体，特别是一种生产非外消旋环氧酯的过程，这种环氧酯在制备药物化合物的中间体中有用。
• Intermediates for preparing epoxy esters
  申请人：SmithKline Beecham Corp.

  公开号：US05208353A1

  公开（公告）日：1993-05-04

  This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.

  本发明涉及一种制备环氧酯的方法，以及由此方法制备的中间体，特别是一种生产非外消旋环氧酯的方法，该方法用于制备制药化合物的中间体。
• PROCESS AND INTERMEDIATE FOR THE PREPARATION OF 2-HYDROXY-3-SULFIDO-3-PHENYL PROPANOIC ACIDS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0541706A1

  公开（公告）日：1993-05-19
• EP0541706A4
  申请人：——

  公开号：EP0541706A4

  公开（公告）日：1993-12-01