2-trimethylsilyl-3-furanmethanol | 101822-35-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-trimethylsilyl-3-furanmethanol
• 英文别名: 3-(2-trimethylsilyl)furylmethanol；[2-(trimethylsilyl)furan-3-yl]methanol；3-Furanmethanol, 2-(trimethylsilyl)-；(2-trimethylsilylfuran-3-yl)methanol
• CAS: 101822-35-9
• 化学式: C₈H₁₄O₂Si
• 分子量: 170.283
• InChiKey: HJSQDOWWTFLSNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-trimethylsilyl-3-furanmethanol 在 四丁基氟化铵 、 三溴化磷 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 夏至草素
  参考文献：
  名称：

  Marrubiin 和相关拉丹丹二萜内酯的全合成

  摘要：

  描述了拉丹二萜内酯 marrubiin、marrulibacetal、desertine、marrulibacetal A、marrubasch F、cylenine C、marrulanic acid 和 marrulactone 的全合成。这些分子的反式萘烷部分是通过 Pauson-Khand 反应以立体选择性方式构建的，所得环戊烯酮被氧化裂解形成内酯环。C9 侧链的延长是通过与各种亲核试剂的环氧化物开环反应实现的，官能团操作完成了这些天然产物的合成。沙漠的立体化学可以通过转化来建立。

  DOI：

  10.3390/molecules25071610
• 作为产物：
  描述：

  2-Trimethylsilyl-3-furancarboxylic acid 在 lithium aluminium tetrahydride 作用下， 生成 2-trimethylsilyl-3-furanmethanol
  参考文献：
  名称：

  共轭二烯酮与呋喃的环烷基化

  摘要：

  使用基于呋喃的环烷基化策略制备具有愈创木酚内酯和假愈创木瓜内酯显着特征的熔融三环化合物。

  DOI：

  10.1016/s0040-4039(00)73274-6

文献信息

• The inhibitory mechanism of bovine pancreatic phospholipase A2 by aldehyde terpenoids
  作者：Katsunori Tanaka、Mitsunobu Kamatani、Hajime Mori、Shinobu Fujii、Kiyoshi Ikeda、Miki Hisada、Yasuhiro Itagaki、Shigeo Katsumura

  DOI：10.1016/s0040-4020(98)01197-1

  日期：1999.2

  We established the stereoselective synthesis of (E)-3-methoxycarbonyl-2,4,6-trienal compound A and discovered that the compound A showed more powerful inhibitory activity toward phospholipase A2(PLA2) from bovine pancreas than manoalide which is a typical PLA2 inhibitor. As the inhibitory mechanism of PLA2 by A, the irreversible formation of dihydropyridine derivative resulting from the reaction of

  我们建立了（E）-3-甲氧基羰基-2,4,6-三烯醛化合物A的立体选择性合成方法，发现该化合物A对牛胰腺中磷脂酶A 2（PLA 2）的抑制作用比对作为主体的MAnoalide具有更强的抑制作用。典型的PLA 2抑制剂。作为PLA的抑制机构2由甲，二氢吡啶衍生物由此而来从反应不可逆地形成甲与PLA赖氨酸残基2是基于模型的反应方案。此外，A 通过MALDI-TOF-MS肽图分析发现，Lys56被选择性地修饰了包括在该酶的界面识别位点中的Lys56。
• The regiospecific formation and reactions of 4-lithio-2-(t-butyldimethylsilyl)- 3-(hydroxymethyl)furan: An approach to 3,4-disubstituted furans.
  作者：Edward J. Bures、Brian A. Keay

  DOI：10.1016/s0040-4039(00)80267-1

  日期：1988.1

  4-Lithio-2-(t-butyldimethylsilyl)-3-(hydroxymethyl)furan, generated by treating 2-(t-butyldimethylsilyl)-3-(hydroxymethyl)furan with 2.2 equivalents of n-butyllithium (DME/0°C/15 min), is trapped by a variety of electrophiles to produce, after desilylation, 3,4-disubstituted furans in good to moderate yields.

  通过用2.2当量的正丁基锂（DME / 0°C /在15分钟内）被各种亲电试剂捕获，去甲硅烷基化后可产生3,4-二取代的呋喃，产率中等至中等。
• Regiospecific synthesis of γ-hydroxybutenolide. Photosensitized oxygenation of substituted 2-trimethylsilylfuran
  作者：Shigeo Katsumura、Keiko Hori、Shinya Fujiwara、Sachihiko Isoe

  DOI：10.1016/s0040-4039(00)98769-0

  日期：——

  Regiospecific synthesis of substituted γ-hydroxybutenolide was accomplished by photosensitized oxygenation of 2-trimethylsilyl-furan derivatives, and chemoselective oxidation of furan ring having tri- and tetra-substituted olefins in the side chain was also achieved.

  通过对2-三甲基甲硅烷基-呋喃衍生物进行光敏氧化来完成取代的γ-羟基丁烯内酯的区域特异性合成，并且还实现了在侧链具有三和四取代的烯烃的呋喃环的化学选择性氧化。
• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2.¹ Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
  作者：Edward Bures、James A. Nieman、Shuyuan Yu、Patrick G. Spinazzé、Jean-Louis J. Bontront、Ian R. Hunt、Arvi Rauk、Brian A. Keay

  DOI：10.1021/jo971098b

  日期：1997.12.1

  A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.
• Dong, Jia-Qiang; Wong, Henry N. C., Angewandte Chemie - International Edition, 2009, vol. 48, p. 2351 - 2354
  作者：Dong, Jia-Qiang、Wong, Henry N. C.

  DOI：——

  日期：——