4,4,6-trimethyl-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]-1,3-oxazinane | 391869-91-3

• 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: 4,4,6-trimethyl-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]-1,3-oxazinane
• CAS: 391869-91-3
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: UUVTZIMSKBTJCB-JWIMFUQQSA-N

物化性质

• 沸点：
  427.7±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-色氨酸甲酯 、 4,4,6-trimethyl-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]-1,3-oxazinane 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以35%的产率得到(cis,SR)-methyl-1-(p-tolylsulfinylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines

  摘要：

  2-(p-Tolylsulfinylmethyl)oxazinane, a chiral carbonyl equivalent, has been synthesised and used for the diastereoselective synthesis of tetrahydro-beta-carbolines including intermediates of yohimbine and herman alkaloids. A fair degree of diastereoselectivity, comparable with other approaches, has been achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.062
• 作为产物：
  描述：

  4,4,6-Trimethyl-2-((R)-toluene-4-sulfinylmethyl)-5,6-dihydro-4H-[1,3]oxazine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.0h， 以100%的产率得到4,4,6-trimethyl-2-[[(R)-(4-methylphenyl)sulfinyl]methyl]-1,3-oxazinane
  参考文献：
  名称：

  2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines

  摘要：

  2-(p-Tolylsulfinylmethyl)oxazinane, a chiral carbonyl equivalent, has been synthesised and used for the diastereoselective synthesis of tetrahydro-beta-carbolines including intermediates of yohimbine and herman alkaloids. A fair degree of diastereoselectivity, comparable with other approaches, has been achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.062

文献信息

• 2-Arylsulfinylmethyloxazines: Chiral Carbonyl Equivalents
  作者：Kamaljit Singh、Prasant K. Deb、Sonia Behal

  DOI：10.3987/com-01-9263

  日期：——

  A single pot acid catalysed condensation reaction of 2-arylsulfinylmethyloxazinane - a chiral carbonyl equivalent (derived from the title oxazine by BH4- reduction) with tryptamine and tryptophan esters, furnishes tetrahydro-beta -carbolines and can be subsequently transformed into indole alkaloids.
• 2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines
  作者：Kamaljit Singh、Sonia Behal、Prasant K. Deb

  DOI：10.1016/j.tet.2004.07.062

  日期：2004.10

  2-(p-Tolylsulfinylmethyl)oxazinane, a chiral carbonyl equivalent, has been synthesised and used for the diastereoselective synthesis of tetrahydro-beta-carbolines including intermediates of yohimbine and herman alkaloids. A fair degree of diastereoselectivity, comparable with other approaches, has been achieved. (C) 2004 Elsevier Ltd. All rights reserved.