(2R)-trans-(+) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxamide | 134511-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R)-trans-(+) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxamide
• 英文别名: (2R-trans)-3-[2-(8-phenyloctyl)phenyl]oxiranecarboxamide；(2R,3S)-3-[2-(8-phenyloctyl)phenyl]oxirane-2-carboxamide
• CAS: 134511-44-7
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: NIBXDTCADAWHLE-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-巯基丙酸甲酯 、 (2R)-trans-(+) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxamide 生成 *,S^*)>-α-Hydroxy-β-<<2-(methoxycarbonyl)ethyl>thio>-2-(8-phenyloctyl)benzenepropanamide
  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,3S)-(+) methyl 2,3-epoxy-3-<2-(8-phenyloctyl)phenyl>propionate 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(2R)-trans-(+) 3-<2-(8-phenyloctyl)phenyl>oxiranecarboxamide
  参考文献：
  名称：

  1,2-二醇立体定向转化为环氧化物的简化程序

  摘要：

  已经开发出一种简单的“一锅法”程序，用于通过卤代醇酯中间体将邻位二醇转化为环氧化物。该方法可耐受包括酸敏感性官能团在内的多种官能团。变换进行经由环状acetoxonium中间的一个，通常是高度选择性，亲核开口，由环状原乙酸酯和Me产生3用SiCl，乙酰溴或乙酰氯/ NaI分别形成1-乙酰氧基-2-氯化物，1-乙酰氧基-2-溴化物或1-乙酰氧基-2-碘化物中间体。即使有苄基底物也不会发生差向异构。随后的碱介导的甲醇分解以优异的总收率提供了环氧化物。从3- [2-（8-苯基辛基）苯基]丙酸甲酯的高度对映选择性顺式-二羟基化开始，该方法的应用导致白三烯拮抗剂SKF 104353的有效形式合成。

  DOI：

  10.1016/s0040-4020(01)88349-6

文献信息

• 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，以及由该过程制备的中间体，特别是一种能够用作制备医药化合物中间体的非外消旋环氧酯制备过程。
• Chelation control in metal-assisted aldol addition reactions of .alpha.-N-halogenated imide enolates leading to predominantly anti stereoselectivity. An example of a stereocontrolled Darzens reaction
  作者：Lendon N. Pridgen、Ahmed F. Abdel-Magid、I. Lantos、Susan Shilcrat、Drake S. Eggleston

  DOI：10.1021/jo00071a020

  日期：1993.9

  The aldol reaction of enantiopure N-(haloacetyl)-2-oxazolidinone enolates with aromatic aldehydes was studied for conditions that would induce the reaction to yield predominantly anti adducts. It was found herein that the inherent steric and stereoelectronic properties of the aldehyde (R), as well as its chelative ability with the enolate countercation, are crucial in determining which of its enantiotopic faces reacts. Certain metallic enolates (Sn,IV Zn, and Li) are postulated to react through a three-point coordination transition state to yield mainly anti adducts, while others (Sn,II B, Ti) are shown to react via noncoordinated transition states to yield either syn or anti adducts. X-ray crystallography was instrumental in fully defining the absolute stereochemistry of each product, providing insight into the mechanisms of stereocontrol. The major anti producing pathway for reaction of aromatic aldehydes is postulated to proceed via boatlike or a high-energy ''unfavored chair'' transition state (TS). Finally, using our protocol of varying either the enolate countercation or the substitution pattern on the aromatic aldehyde, we demonstrate how one may synthesize three of the four possible stereoisomers available from this aldol-type reaction, the syn Li isomers 7 being the only inaccessible isomer as a major product in this alpha-halo-2-oxazolidinone system. The anti halohydrins were converted stereospecifically to the trans epoxy esters or epoxy amides in high enantiomeric purity.
• Phenylglycidamides useful for preparing alpha-hydroxy-beta-sulfido-arylpropionic acid derivatives
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0403250B1

  公开（公告）日：1994-11-23
• Leukotriene antagonists
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0403249B1

  公开（公告）日：1994-04-27
• JPH0334974A
  申请人：——

  公开号：JPH0334974A

  公开（公告）日：1991-02-14