(6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol | 228114-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol
• 英文别名: {6-[(tert-butyldimethylsilyl)oxy]-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl}methanol；[6-[tert-butyl(dimethyl)silyl]oxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl]methanol
• CAS: 228114-44-1
• 化学式: C₂₀H₃₄O₃Si
• 分子量: 350.574
• InChiKey: KAGOPTSULYPVCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol 在 sodium hydroxide 哌啶 、 盐酸 、 sodium tetrahydroborate 、 N,N-二甲基甘氨酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.25h， 生成 曲格列酮
  参考文献：
  名称：

  Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

  摘要：

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.087
• 作为产物：
  描述：

  6-(tert-butyldimethylsilanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 反应 3.0h， 生成 (6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol
  参考文献：
  名称：

  Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

  摘要：

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.087

文献信息

• Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium
  作者：Yun-Hua Fan、Han Chen、Amarnath Natarajan、Yuhong Guo、Fred Harbinski、Julia Iyasere、William Christ、Huseyin Aktas、Jose A. Halperin

  DOI：10.1016/j.bmcl.2004.02.087

  日期：2004.5

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.