(5R,6S)-6-Phenyl-7-(toluene-4-sulfonyl)-1-oxa-7-aza-spiro[4.5]deca-3,9-diene | 335151-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5R,6S)-6-Phenyl-7-(toluene-4-sulfonyl)-1-oxa-7-aza-spiro[4.5]deca-3,9-diene
• 英文别名: (5R,10S)-9-(4-methylphenyl)sulfonyl-10-phenyl-1-oxa-9-azaspiro[4.5]deca-3,6-diene
• CAS: 335151-04-7
• 化学式: C₂₁H₂₁NO₃S
• 分子量: 367.469
• InChiKey: LIFRQZCUXBBQSD-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6S)-6-Phenyl-7-(toluene-4-sulfonyl)-1-oxa-7-aza-spiro[4.5]deca-3,9-diene 在 palladium dihydroxide 、 三乙胺 、 lithium chloride palladium diacetate 、 四丁基氯化铵 、 氢气 、 potassium formate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 2-[(3R,5R,6S)-6-Phenyl-7-(toluene-4-sulfonyl)-1-oxa-7-aza-spiro[4.5]dec-3-yl]-4-trifluoromethoxy-phenol
  参考文献：
  名称：

  A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists

  摘要：

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

  DOI：

  10.1021/ol006958g
• 作为产物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 在 N,N-二甲基丙烯基脲 、 cerium(III) chloride 、 (bis(tricyclohexyl)phosphine)ruthenium(II) dichloride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 22.0h， 生成 (5R,6S)-6-Phenyl-7-(toluene-4-sulfonyl)-1-oxa-7-aza-spiro[4.5]deca-3,9-diene
  参考文献：
  名称：

  A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists

  摘要：

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

  DOI：

  10.1021/ol006958g

文献信息

• Use of Commercially Available Ruthenium Fischer-Type Carbenes for Ring-Closing Metathesis Reactions: Scope and Limitations of an<i>in situ</i>Activation Procedure
  作者：Debra J. Wallace

  DOI：10.1002/adsc.200900301

  日期：2009.10

  An evaluation of two commercially available Fischer-type ruthenium carbenes in a range of ring-closing diene and enyne metathesis reactions has been carried out. A method to activate such catalysts for ring-closing reactions is presented.

  在闭环二烯和烯炔复分解反应的范围内，已经对两种市售的菲舍尔型钌碳烯进行了评价。提出了一种活化此类催化剂以进行闭环反应的方法。
• On the mechanism of a double ring-closing metathesis reaction
  作者：Debra J. Wallace

  DOI：10.1016/j.tetlet.2004.11.149

  日期：2005.1

  A detailed study of the steps involved in the double ring-closing metathesis reaction of 2 to 3 has been carried out. Both the selectivity and mechanism were affected by choice of catalyst.

  已对2至3的双环复分解反应所涉及的步骤进行了详细研究。选择性和机理均受催化剂选择的影响。
• A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists
  作者：Debra J. Wallace、Jonathan M. Goodman、Derek J. Kennedy、Antony J. Davies、Cameron J. Cowden、Michael S. Ashwood、Ian F. Cottrell、Ulf-H. Dolling、Paul J. Reider

  DOI：10.1021/ol006958g

  日期：2001.3.1

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.