bicyclo[4.1.0]heptane-7-carboxylic acid | 21448-77-1

• 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: bicyclo[4.1.0]heptane-7-carboxylic acid
• 英文别名: (1α,6α,7α)-bicyclo[4.1.0]heptane-7-carboxylic acid；Bicyclo<4.1.0>heptan-exo-7-carbonsaeure-ethylester；bicyclo<4.1.0>heptane-exo-7-carboxylic acid；exo-bicyclo<4.1.0>heptane-7-carboxylic acid；(1rH.6cH)-norcarane-carboxylic acid-(7c)；(1rH.6cH)-Norcaran-carbonsaeure-(7c)；exo-Bicyco<4.1.0>heptan-7-carboxylic acid
• CAS: 21448-77-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: PNTAWGJKWLLAAW-ZMONIFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  bicyclo[4.1.0]heptane-7-carboxylic acid 以69%的产率得到
  参考文献：
  名称：

  KIRMSE W.; JENDRALLA H., CHEM. BER., 1978, 111, NO 5, 1857-1872

  摘要：

  DOI：
• 作为产物：
  描述：

  exo-(bicyclo[4.1.0]hept-7-yl)(phenyl)methanone 生成 bicyclo[4.1.0]heptane-7-carboxylic acid
  参考文献：
  名称：

  Chemistry of carbanions. XX. Comparison of .alpha.-chloro enolate anions and .alpha.-diazo ketones

  摘要：

  DOI：

  10.1021/jo00821a034

文献信息

• Ring-opening of some radicals containing the cyclopropylmethyl system
  作者：Athelstan L. J. Beckwith、Graeme Moad

  DOI：10.1039/p29800001473

  日期：——

  Mono- and bi-cyclic radicals containing the cyclopropylmethyl system are readily generated by interaction of the appropriate halides with triphenyl- or tributyl-stannane. Each radical studied underwent ring-opening by fission of the more substituted βγ-bond. In the case of the secondary radical (12b) the new double bond was formed preferentially in the trans-configuration. Rate constants, which cannot

  通过适当的卤化物与三苯基或三丁基锡烷的相互作用，容易产生含有环丙基甲基系统的单环和双环基团。每个被研究的基团都通过更取代的βγ键的裂变而开环。在第二自由基（12b）的情况下，优先以反式构型形成新的双键。无法通过此方法高精度确定的速率常数在1×10 7 –3×10 8 s –1的范围内在25°C下。当通过流动方法在esr腔中产生时，α-羟基环丙基甲基自由基经历β裂变，随后进行1,5-氢原子转移以提供烯氧基。与非极性溶剂相比，后者在水中的反应更慢。刚性羟基降三环基自由基（43）可能会由于过渡态的偶极性质而优先发生取代度较低的βγ键的裂变。
• Maclnnes, Iain; Nonhebel, Derek C.; Orszulik, Stefan T., Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2771 - 2776
  作者：Maclnnes, Iain、Nonhebel, Derek C.、Orszulik, Stefan T.、Suckling, Colin J.、Wrigglesworth, Roger

  DOI：——

  日期：——
• Discovery of GS-9669, a Thumb Site II Non-Nucleoside Inhibitor of NS5B for the Treatment of Genotype 1 Chronic Hepatitis C Infection
  作者：Scott E. Lazerwith、Willard Lew、Jennifer Zhang、Philip Morganelli、Qi Liu、Eda Canales、Michael O. Clarke、Edward Doerffler、Daniel Byun、Michael Mertzman、Hong Ye、Lee Chong、Lianhong Xu、Todd Appleby、Xiaowu Chen、Martijn Fenaux、Ahmad Hashash、Stephanie A. Leavitt、Eric Mabery、Mike Matles、Judy W. Mwangi、Yang Tian、Yu-Jen Lee、Jingyu Zhang、Christine Zhu、Bernard P. Murray、William J. Watkins

  DOI：10.1021/jm401420j

  日期：2014.3.13

  Investigation of thiophene-2-carboxylic acid HCV NS5B site II inhibitors, guided by measurement of cell culture medium binding, revealed the structure activity relationships for intrinsic cellular potency. The pharmacokinetic profile was enhanced through incorporation of heterocyclic ethers on the N-alkyl substituent. Hydroxyl groups were incorporated to modulate protein binding. Intrinsic potency was further improved through enantiospecific introduction of an olefin in the N-acyl motif, resulting in the discovery of the phase 2 clinical candidate GS-9669. The unexpected activity of this compound against the clinically relevant NS5B M423T mutant, relative to the wild type, was shown to arise from both the N-alkyl substituent and the N-acyl group.
• Buttinelli, Paolo; Gargaro, Giuseppe; Loreto, M. Antonietta, Gazzetta Chimica Italiana, 1985, vol. 115, # 3, p. 155 - 158
  作者：Buttinelli, Paolo、Gargaro, Giuseppe、Loreto, M. Antonietta、Pellacani, Lucio、Tardella, Paolo A.

  DOI：——

  日期：——
• Kirmse, Wolfgang; Ritzer, Joachim, Chemische Berichte, 1985, vol. 118, # 12, p. 4987 - 4996
  作者：Kirmse, Wolfgang、Ritzer, Joachim

  DOI：——

  日期：——