ethyl 2-bicyclo<4.1.0>heptylacetate | 260983-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-bicyclo<4.1.0>heptylacetate
• 英文别名: Ethyl 2-(1-bicyclo[4.1.0]heptanyl)acetate
• CAS: 260983-23-1
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: GSGOMBJQVSVJLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  ethyl 2-bicyclo<4.1.0>heptylacetate 在 氢氧化钾 、 乙醇 作用下， 反应 2.0h， 以92%的产率得到Bicyclo<4.1.0>heptane-1-acetic acid
  参考文献：
  名称：

  Six- vs Seven-Membered Ring Formation from the 1-Bicyclo[4.1.0]heptanylmethyl Radical:  Synthetic and ab Initio Studies

  摘要：

  The viability of utilizing 1-bicyclo[4.1.0]heptanylmethyl radical (3) to serve as a progenitor of seven-membered carbocycles was examined. Rate constants for the rearrangement of this radical to 3-methylenecycloheptyl radical (4) and 2-methylenecyclohexyl-1-methyl radical (6) were measured using the competition method of 3 with thiophenol over the temperature range of -75 to 59 degrees C. Arrhenius functions were calculated for the conversions of 3 to 4 and 3 to 6 and found to be log (k/s(-1)) = (12.38 +/- 0.20) - (5.63 +/- 0.23)/theta and log(k/s(-1)) = (11.54 +/- 0.32) - (5.26 +/- 0.37)/theta, respectively. The rate-constants for these conversions at 25 degrees C are 1.86 x 10(8) s(-1) and 5.11 x 10(7) s(-1), respectively. Hence, the seven-membered ring-expanded carbocycle is formed 3.6 times faster at 25 degrees C than the nonexpanded species. This suggests that the 1-bicyclo[4.1.0]heptanylmethyl radical system may be synthetically useful in seven-membered ring-forming methodology. Preliminary theoretical examination of this radical system qualitatively predicted the experimentally determined energies of activation: PMP4/6-31G*//HF/6-31G* Delta E-a (3 --> 6 - 3 --> 4) = 3.0 kcal/mol with zero point-energy correction. The HF/6-31G* optimized reaction coordinate stationary points suggest cyclopropyl substituent eclipsing interactions play an important role in determining the kinetic outcome of these rearrangements.

  DOI：

  10.1021/jo981708n
• 作为产物：
  描述：

  2-(环己烯-1-基)乙酸乙酯 、 二碘甲烷 在 diethylzinc 作用下， 生成 ethyl 2-bicyclo<4.1.0>heptylacetate
  参考文献：
  名称：

  Six- vs Seven-Membered Ring Formation from the 1-Bicyclo[4.1.0]heptanylmethyl Radical:  Synthetic and ab Initio Studies

  摘要：

  The viability of utilizing 1-bicyclo[4.1.0]heptanylmethyl radical (3) to serve as a progenitor of seven-membered carbocycles was examined. Rate constants for the rearrangement of this radical to 3-methylenecycloheptyl radical (4) and 2-methylenecyclohexyl-1-methyl radical (6) were measured using the competition method of 3 with thiophenol over the temperature range of -75 to 59 degrees C. Arrhenius functions were calculated for the conversions of 3 to 4 and 3 to 6 and found to be log (k/s(-1)) = (12.38 +/- 0.20) - (5.63 +/- 0.23)/theta and log(k/s(-1)) = (11.54 +/- 0.32) - (5.26 +/- 0.37)/theta, respectively. The rate-constants for these conversions at 25 degrees C are 1.86 x 10(8) s(-1) and 5.11 x 10(7) s(-1), respectively. Hence, the seven-membered ring-expanded carbocycle is formed 3.6 times faster at 25 degrees C than the nonexpanded species. This suggests that the 1-bicyclo[4.1.0]heptanylmethyl radical system may be synthetically useful in seven-membered ring-forming methodology. Preliminary theoretical examination of this radical system qualitatively predicted the experimentally determined energies of activation: PMP4/6-31G*//HF/6-31G* Delta E-a (3 --> 6 - 3 --> 4) = 3.0 kcal/mol with zero point-energy correction. The HF/6-31G* optimized reaction coordinate stationary points suggest cyclopropyl substituent eclipsing interactions play an important role in determining the kinetic outcome of these rearrangements.

  DOI：

  10.1021/jo981708n

文献信息

• Inhibitors of Serine Proteases
  申请人：Farmer Luc

  公开号：US20100272681A1

  公开（公告）日：2010-10-28

  The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.

  本发明涉及抑制丝氨酸蛋白酶活性的化合物，特别是针对丙型肝炎病毒NS3-NS4A蛋白酶的活性。这些化合物通过干扰丙型肝炎病毒的生命周期来发挥作用，并且也可用作抗病毒剂。本发明还涉及包含这些化合物的组合物，无论是用于体外使用还是用于治疗患有HCV感染的患者。本发明还涉及通过给患者注射包含本发明化合物的组合物来治疗HCV感染的方法。
• Inhibitors of serine proteases
  申请人：Cottrell M. Kevin

  公开号：US20070179167A1

  公开（公告）日：2007-08-02

  The present invention relates to compounds of formula I: or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

  本发明涉及式I的化合物：或其药物可接受的盐或混合物，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒NS3-NS4A蛋白酶的活性。
• INHIBITORS OF SERINE PROTEASES
  申请人：Cottrell Kevin M.

  公开号：US20110165120A1

  公开（公告）日：2011-07-07

  The present invention relates to compounds of formula I: or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

  本发明涉及式I的化合物：或其药学上可接受的盐或混合物，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒NS3-NS4A蛋白酶的活性。
• Spirocyclic inhibitors of serine proteases for the treatment of hcv infections
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2631238A1

  公开（公告）日：2013-08-28

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

  本发明涉及式（I）化合物或其药学上可接受的盐。这些化合物可抑制丝氨酸蛋白酶，特别是丙型肝炎病毒 NS3-NS4A 蛋白酶。
• US7985762B2
  申请人：——

  公开号：US7985762B2

  公开（公告）日：2011-07-26