(1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol | 180187-46-6

• 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: (1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol
• CAS: 180187-46-6
• 化学式: C₁₃H₂₆O₂Si
• 分子量: 242.434
• InChiKey: KNMQKEDIDHQVIG-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol 在 甲醇 、 sodium hydroxide 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 9-[(1S,2R)-2-(2-Hydroxy-ethyl)-cyclopent-3-enyl]-9H-purin-6-ol
  参考文献：
  名称：

  对映选择性合成2- [5-（9 H-嘌呤-9-基）-2-环戊烯-1-基]-乙醇类似物作为潜在的抗病毒药

  摘要：

  描述了2- [5-（9 H-嘌呤-9-基）-2-环戊烯-1-基]乙醇类似物的对映选择性合成。（1R，5R）-[1-（叔丁基二甲基甲硅烷氧基）乙基] -2-环戊烯-5-醇4a和（1S，5S）-[1-（叔丁基二甲基甲硅烷氧基）乙基] -2-环戊烯-5-醇使用Mitsunobu反应条件将4b与6-氯嘌呤和2-氨基-6-氯嘌呤偶联。测试了化合物6a和b，7a和b，8a和b，9a和b以及10a和b的抗病毒活性。

  DOI：

  10.1016/0040-4020(96)00412-7
• 作为产物：
  描述：

  前列腺素中间体 生成 (1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol
  参考文献：
  名称：

  脂肪酶催化拆分 2-取代的 3-环戊烯-1-醇衍生物

  摘要：

  2-氧杂双环[3.3.0]oct-6-en-3-one是前列腺素合成中的关键中间体，在转化为2-[2-(叔丁基二甲基甲硅烷氧基)后，利用脂肪酶进行了有效的光学拆分乙基]-3-环戊烯-1-基乙酸酯和2-[2-(N,N-二甲基氨基甲酰基)甲基]-3-环戊烯-1-基乙酸酯。

  DOI：

  10.1246/cl.1991.1651

文献信息

• Kinetic Resolution of Racemic 2-Substituted 3-Cyclopenten-1-ols by Lipase-Catalyzed Transesterifications:  A Rational Strategy To Improve Enantioselectivity
  作者：Tadashi Ema、Soichi Maeno、Yusuke Takaya、Takashi Sakai、Masanori Utaka

  DOI：10.1021/jo961144s

  日期：1996.1.1

  The effect of the acyl group of acylating agents on the enantioselectivity in the Pseudomonas cepacia lipase-catalyzed acylations of racemic alcohols has been studied. 2-[(N,N-Dimethylcarbamoyl)methyl]-3-cyclopenten-1-ol (1) and 2-[2-(tert-butyldimethylsilyloxy)ethyl]-3-cyclopenten-1-ol (4) were resolved with a variety of enantioselectivities. In the case of alcohol 1, the enantiomeric ratio (the E value) was increased by changing the acylating agent from vinyl acetate (E = 30) to vinyl butyrate (E = 156) and dropped substantially with longer acyl donors. With vinyl chloroacetate, the reaction rate was fast and the enantioselectivity was high (E = 89), whereas the resolution with vinyl trifluoroacetate resulted in a very poor enantioselectivity (E = 4). The bulky acylating agent, vinyl pivalate, gave a moderate enantioselectivity (E = 15). In the case of alcohol 4, the enantioselectivities were excellent (E > 142) except vinyl pivalate (E = 12). It is indicated that the acyl group transiently attached at the active site of the lipase acts as a stereochemical controller. The solvent effect is also described briefly. A clear correlation was observed between the E values and the log P values of the organic solvents; the smaller the log P value of the solvent, the higher the E value.
• Intramolecular .alpha.-amidoalkylation of an olefin for the synthesis of a useful prostaglandin intermediate
  作者：Tsung-Tee Li、Patricia Lesko、Robert H. Ellison、N. Subramanian、John H. Fried

  DOI：10.1021/jo00314a024

  日期：1981.1