(2S,3R,3aS,4aR,6R,8aS)-3-Isopropyl-2,6,9,9-tetramethyl-2-phenylsulfanylmethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one | 634589-07-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3R,3aS,4aR,6R,8aS)-3-Isopropyl-2,6,9,9-tetramethyl-2-phenylsulfanylmethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one
• 英文别名: (1R,3S,4R,5S,9S,12R)-5,8,8,12-tetramethyl-5-(phenylsulfanylmethyl)-4-propan-2-yl-2-oxa-7-azatricyclo[7.4.0.03,7]tridecan-6-one
• CAS: 634589-07-4
• 化学式: C₂₅H₃₇NO₂S
• 分子量: 415.64
• InChiKey: KHSXWOSGJYOXAV-RVQOTRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,3aS,4aR,6R,8aS)-3-Isopropyl-2,6,9,9-tetramethyl-2-phenylsulfanylmethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (3'S,4'R)-8-(3'-methyl-3'-phenylsulfinylmethyl-4'-isopropylpyrrolidinyl)menthol
  参考文献：
  名称：

  Regio- and diastereoselective tandem addition–carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines

  摘要：

  Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.06.003
• 作为产物：
  描述：

  (-)-aminomenthol 在 偶氮二异丁腈 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 (2S,3R,3aS,4aR,6R,8aS)-3-Isopropyl-2,6,9,9-tetramethyl-2-phenylsulfanylmethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one
  参考文献：
  名称：

  Regio- and diastereoselective tandem addition–carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines

  摘要：

  Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.06.003

文献信息

• Regio- and diastereoselective tandem addition–carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines
  作者：Rafael Pedrosa、Celia Andrés、Juan P. Duque-Soladana、Alicia Maestro、Javier Nieto

  DOI：10.1016/j.tetasy.2003.06.003

  日期：2003.10

  Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical. (C) 2003 Elsevier Ltd. All rights reserved.