(S)-3-(tert-butyldimethylsilyloxy)-5-[(R)-1-(tert-butyldimethylsilyloxy)prop-2-ynyl]-5-methylfuran-2(5H)-one | 609842-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-3-(tert-butyldimethylsilyloxy)-5-[(R)-1-(tert-butyldimethylsilyloxy)prop-2-ynyl]-5-methylfuran-2(5H)-one
• 英文别名: (5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyprop-2-ynyl]-5-methylfuran-2-one
• CAS: 609842-76-4
• 化学式: C₂₀H₃₆O₄Si₂
• 分子量: 396.674
• InChiKey: CZQPXKZCOQXESA-UZLBHIALSA-N

物化性质

• 沸点：
  413.0±40.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)-5-[(R)-1-(tert-butyldimethylsilyloxy)prop-2-ynyl]-5-methylfuran-2(5H)-one 在 silver nitrate N-溴代丁二酰亚胺(NBS) 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (S)-5-[(R)-3-bromo-1-hydroxyprop-2-ynyl]-3-hydroxy-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1
• 作为产物：
  描述：

  methyl 2-(tert-butyldimethylsiloxy)-2-(dimethoxyphosphoryl)acetate 、 (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2-methylpent-4-ynal 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(S)-3-(tert-butyldimethylsilyloxy)-5-[(R)-1-(tert-butyldimethylsilyloxy)prop-2-ynyl]-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1

文献信息

• The total synthesis and biological evaluation of nafuredin-γ and its analogues
  作者：Tohru Nagamitsu、Daisuke Takano、Miyuki Seki、Shiho Arima、Masaki Ohtawa、Kazuro Shiomi、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.06.066

  日期：2008.8

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.