2-(2-Hydroxy-ethyl)-cyclopent-3-enol | 587875-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-Hydroxy-ethyl)-cyclopent-3-enol
• 英文别名: 2-(2-Hydroxyethyl)cyclopent-3-en-1-ol
• CAS: 587875-02-3
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: UPMJCBJKDZVWNI-UHFFFAOYSA-N

物化性质

• 沸点：
  245.1±15.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Hydroxy-ethyl)-cyclopent-3-enol 在 咪唑 、 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.5h， 生成 [2-(5-Benzyloxy-cyclopent-2-enyl)-ethoxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  3-烷基-1,2-环戊二酮的不对称氧化。第3部分：3-羟乙基-1,2-环戊二酮的氧化环裂解：α-羟基-γ-内酯酸和螺-γ-二内酯的合成

  摘要：

  Ti（O i Pr）4 /酒石酸二乙酯/ t BuOOH络合物将3-羟乙基-1,2-环戊二酮氧化，生成羟基化/环裂解产物-高对映选择性（至多95％ee）的内酯酸，收率良好（高达75％）。这些化合物以良好的产率转化为手性螺-γ-二内酯。

  DOI：

  10.1016/s0957-4166(03)00452-x

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.
• Bicyclic sulfonamide derivatives
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0226346B1

  公开（公告）日：1991-08-14
• US3933892A
  申请人：——

  公开号：US3933892A

  公开（公告）日：1976-01-20
• US4115452A
  申请人：——

  公开号：US4115452A

  公开（公告）日：1978-09-19
• US4127736A
  申请人：——

  公开号：US4127736A

  公开（公告）日：1978-11-28