(4S6R,4S6S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one | 1020850-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S6R,4S6S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one
• 英文别名: (4S,6RS)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one；(4S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one；(4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-methylcyclohex-2-en-1-one
• CAS: 1020850-34-3
• 化学式: C₁₃H₂₄O₂Si
• 分子量: 240.418
• InChiKey: VRTSKDNGIAEZAS-RRKGBCIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S6R,4S6S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one 在 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (1SR,3RS,6RS)-1-hydroxy-7⁽¹⁴⁾,10-bisaboladien-4-one
  参考文献：
  名称：

  Concise Synthesis of an Antifeedant Sesquiterpene againstLocusta migratoria

  摘要：

  从日本柳杉中分离出一种抗蝗虫的物质（1S *，3R *，6R *）-1-羟基-7（14），10-双叶二烯-4-酮，简称“抗蝗虫物质”，它是从4-羟基-2-环己烯酮开始的。

  DOI：

  10.1271/bbb.90878
• 作为产物：
  描述：

  (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以55%的产率得到(4S6R,4S6S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  望远镜式分子内迈克尔/烯化（TIMO）方法制备α-亚烷基-γ-丁内酯：（+）-pa内酯B的合成。

  摘要：

  DOI：

  10.1002/anie.200705329

文献信息

• The Preparation of α-Alkylidene-γ-Butyrolactones Using a Telescoped Intramolecular Michael/Olefination (TIMO) Sequence: Synthesis of (+)-Paeonilactone B
  作者：Michael G. Edwards、Martin N. Kenworthy、Russell R. A. Kitson、Alexis Perry、Mark S. Scott、Adrian C. Whitwood、Richard J. K. Taylor

  DOI：10.1002/ejoc.200800558

  日期：2008.10

  A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to α-alkylidene-γ-butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran-2,5-diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)-paeonilactone B in enantiomerically pure form

  一种新型的分子内迈克尔加成/质子转移/HWE烯化序列已被开发出来，可以快速获得α-亚烷基-γ-丁内酯。这种方法已被应用于制备一系列四氢苯并呋喃-2,5-二酮和相关系统，并且还用于以对映体纯形式合成极短的天然产物 (+)-芍药内酯 B。此外，描述了通过 π-烯丙基中间体进行的钯催化变体的初步实验。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Synthesis, cytotoxicity and inhibition of NO production of ivangustin enantiomer analogues
  作者：Xiang-Yang Qin、Bing-Yang Chen、Jian-Jun Fu、Lei Shan、Xiao-Guang Lei、Wei-Dong Zhang

  DOI：10.1016/j.ejmech.2015.07.051

  日期：2015.9

  The eight novel ivangustin enantiomer analogues possessing alpha-methylene-gamma-butyrolactone moiety have been synthesized using (4S6R, 4S6S)-4-tert-butyldimethylsilyloxy-6-methylcyclohex-2-en-1-one (1) as starting material. These transformations were mainly carried out by aldol condensation reaction and one-pot annelation procedure. The stereochemistry of these synthesized analogues was determined by NOE analysis. Their cytoxicity was evaluated against the human cancer cell lines HCT-116 (colon), HL-60 (leukemia), QGY-7701 (liver), SMMC-7721 (liver), A549 (lung), MCF-7 (breast). The results showed that these analogues were more selective against the cell lines HL-60 and QGY-7701. Analogue 17 exhibited potent cytotoxicity and high selectivity toward HL-60 cell line with IC50 value of 1.02 mu M, which suggested that it might be a promising anti-cancer lead compound. The inhibitory activities against NO production and the cytotoxicities in RAW 264.7 macrophages were determined at the same time. All of the analogues significantly inhibited the NO production with IC50 value in the range of 3.44-6.99 mu M. Analogues 17, 22, 23 and 7 showed higher cytotoxicities, indicated their inhibitory activities against NO production may be influenced by the cytotoxicities. (C) 2015 Elsevier Masson SAS. All rights reserved.