2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol | 928618-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol
• 英文别名: 4-[(tertbutydimethylsilyl)oxy]-2-(hydroxymethyl)cyclohex-2-ene-1-one
• CAS: 928618-21-7
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: IWERTSFOQDMLCE-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 四丁基氟化铵 、 氯化二乙基铝 、 tetraethyl-ammonium, trichloride 、 lithium carbonate 、 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.67h， 生成 (1R,4aR,10aS)-4a-(chloromethyl)-1-hydroxy-1,2,4a,5,6,7,8,9,10,10a-decahydrophenanthren-9-one
  参考文献：
  名称：

  A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures

  摘要：

  A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.

  DOI：

  10.1021/ol500265v
• 作为产物：
  描述：

  聚合甲醛 、 (+/-)-4-(tert-butyl(dimethyl)silyloxy)-2-cyclohexen-1-one 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol
  参考文献：
  名称：

  The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties

  摘要：

  The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A. are described. The target structures were selected in order to probe the influence of several key structural parameters on in vitro anti-cancer bioactivity. The results of a cytotoxicity bioassay of the compounds against non-small-cell lung cancer cell lines A549 and H460 are reported. The biological data provides useful information, which will help guide the future design of compounds in this class with enhanced anti-cancer activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.072

文献信息

• Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties
  作者：Claire L. Arthurs、Natasha S. Wind、Roger C. Whitehead、Ian J. Stratford

  DOI：10.1016/j.bmcl.2006.09.072

  日期：2007.1

  The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented. (c) 2006 Published by Elsevier Ltd.