tert-butyl 2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)-1,3-dioxan-5-ylcarbamate | 1427308-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)-1,3-dioxan-5-ylcarbamate
• 英文别名: tert-butyl N-[2,2-dimethyl-5-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]-1,3-dioxan-5-yl]carbamate
• CAS: 1427308-22-2
• 化学式: C₂₅H₄₀BNO₆
• 分子量: 461.407
• InChiKey: MZXHOKVNYKFXHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)-1,3-dioxan-5-ylcarbamate 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 2-氨基-2-[2-(4-辛基苯基)乙基]-1,3-丙二醇
  参考文献：
  名称：

  Suzuki coupling based synthesis and in vitro cytotoxic evaluation of Fingolimod and analogues

  摘要：

  A concise synthesis of Fingolimod (FTY720) and its analogues was described. The key step involved Suzuki coupling of arylboronate 11 with different bromides. In addition, the newly synthesized Fingolimod analogues (5a-i and 6a-c) were evaluated for their in vitro cytotoxicity against SMCC-7721 and HL-60 cell lines. The preliminary SAR was discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.030
• 作为产物：
  描述：

  (5-甲酰基-2,2-二甲基-1,3-二氧六环-5-基)氨基甲酸叔丁酯 在 亚硝酸特丁酯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 tert-butyl 2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)-1,3-dioxan-5-ylcarbamate
  参考文献：
  名称：

  Suzuki coupling based synthesis and in vitro cytotoxic evaluation of Fingolimod and analogues

  摘要：

  A concise synthesis of Fingolimod (FTY720) and its analogues was described. The key step involved Suzuki coupling of arylboronate 11 with different bromides. In addition, the newly synthesized Fingolimod analogues (5a-i and 6a-c) were evaluated for their in vitro cytotoxicity against SMCC-7721 and HL-60 cell lines. The preliminary SAR was discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.030

文献信息

• Suzuki coupling based synthesis and in vitro cytotoxic evaluation of Fingolimod and analogues
  作者：Tie-Wen Mei、Yu Luo、Xiang-Jun Feng、Wei Lu、Bo Yang

  DOI：10.1016/j.tet.2013.02.030

  日期：2013.4

  A concise synthesis of Fingolimod (FTY720) and its analogues was described. The key step involved Suzuki coupling of arylboronate 11 with different bromides. In addition, the newly synthesized Fingolimod analogues (5a-i and 6a-c) were evaluated for their in vitro cytotoxicity against SMCC-7721 and HL-60 cell lines. The preliminary SAR was discussed. (C) 2013 Elsevier Ltd. All rights reserved.