Bicyclo<4.1.0>heptane-1-acetic acid | 131469-79-9

• 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: Bicyclo<4.1.0>heptane-1-acetic acid
• 英文别名: 2-bicyclo<4.1.0>heptylacetic acid；2-(1-bicyclo[4.1.0]heptyl)acetic acid；2-(bicyclo[4.1.0]heptan-1-yl)acetic acid；bicyclo[4.1.0]heptylacetic Acid；2-(1-bicyclo[4.1.0]heptanyl)acetic acid
• CAS: 131469-79-9
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: LCHODWLQWHOOQS-UHFFFAOYSA-N

物化性质

• 沸点：
  271.7±8.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Bicyclo<4.1.0>heptane-1-acetic acid 在 磷酸 作用下， 以 苯 为溶剂， 反应 8.0h， 以94%的产率得到6-Methyl-7-oxabicyclo<4.3.0>nonan-8-one
  参考文献：
  名称：

  A Convenient Lactonization of 2- and 3-Cyclopropylalkanoic Acids to γ- and δ-Lactones

  摘要：

  本文介绍了一种制备方法，通过3-环丙基链烷酸的酸催化内酯化反应，可方便地获得2,2,4,5,5-五烷基-γ-戊内酯2a-d或2,2,4,4-四烷基-γ-丁内酯4a-e，以及从双环2-环丙基链烷酸5a-d中获取双环-γ-内酯6a-d。

  DOI：

  10.1055/s-1990-27014
• 作为产物：
  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

文献信息

• Synthesis and Pharmacological In Vitro Investigations of Novel Shikonin Derivatives with a Special Focus on Cyclopropane Bearing Derivatives
  作者：Nadine Kretschmer、Antje Hufner、Christin Durchschein、Katrin Popodi、Beate Rinner、Birgit Lohberger、Rudolf Bauer

  DOI：10.3390/ijms22052774

  日期：——

  activity by synthesis. Therefore, we prepared 31, mainly novel shikonin derivatives and screened them in different melanoma cell lines (WM9, WM164, and MUG-Mel2 cells) using the XTT viability assay. We identified (R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl 2-cyclopropyl-2-oxoacetate as a novel derivative with even higher activity. Furthermore, pharmacological investigations

  黑色素瘤是最致命的皮肤癌形式，约占所有皮肤癌死亡人数的四分之三。尤其是在晚期，其治疗具有挑战性，并且存活率非常低。在先前的研究中，我们显示了Onosma paniculata根的成分以及活性最高的成分的合成衍生物在转移性黑色素瘤细胞系中显示出可喜的结果。在当前的研究中，我们解决了我们是否可以通过合成生成具有优化活性的其他衍生物的问题。因此，我们准备了31种主要是新型的紫草素衍生物，并使用XTT活力测定法在不同的黑色素瘤细胞系（WM9，WM164和MUG-Mel2细胞）中对其进行了筛选。我们确定（[R）-1-（1,4-二氢-5,8-二羟基-1,4-二氧杂萘-2-基）-4-甲基戊-3-烯基2-环丙基-2-氧乙酸酯是具有更高活性的新型衍生物。此外，包括ApoToxGlo TM Triplex分析，LDH分析和细胞周期测量在内的药理研究表明，该化合物可诱导凋亡，并减少G1期的细胞，同时增加G2 /
• 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。
• GRF analogs with increased biological potency
  申请人：Theratechnologies, Inc.

  公开号：US20040171534A1

  公开（公告）日：2004-09-02

  The present invention relates to chimeric fatty body-GRF analogs with increased biological potency, their application as anabolic agents and in the diagnosis and treatment of growth hormone deficiencies. The chimeric fatty body-GRF analogs include an hydrophobic moiety (tail), and can be prepared, either by anchoring at least one hydrophobic tail to the GRF, in the chemical synthesis of GRF. The GRF analogs of the present invention are biodegradable, non-immunogenic and exhibit an improved anabolic potency with a reduced dosage and prolonged activity.

  本发明涉及具有增强生物效力的嵌合脂肪体-GRF类似物，它们的应用作为合成代谢剂以及在生长激素缺乏的诊断和治疗中的应用。嵌合脂肪体-GRF类似物包括一个疏水基团（尾部），可以通过在化学合成GRF时将至少一个疏水尾部锚定到GRF上来制备。本发明的GRF类似物是可生物降解的，非免疫原性的，并且具有改善的合成代谢效力，用量减少和活性延长的特点。
• 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。