(+/-)-cis-1-carbomethoxy-2-methylcyclopentane | 80926-05-2

• 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: (+/-)-cis-1-carbomethoxy-2-methylcyclopentane
• 英文别名: methyl (1S,2R)-2-methylcyclopentane-1-carboxylate
• CAS: 80926-05-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: GGIOAOSNSKGXRW-RQJHMYQMSA-N

物化性质

• 沸点：
  172.3±8.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (+/-)-cis-1-carbomethoxy-2-methylcyclopentane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 816.0h， 生成 methyl trans-2-methylcyclopentanecarboxylate
  参考文献：
  名称：

  Structural effects on rates and equilibriums. 23. Effect of .alpha.-amino substituents on rates of formation sp2-hybridized carbanions

  摘要：

  DOI：

  10.1021/jo00348a028
• 作为产物：
  描述：

  cyclopentane-cis-1,2-dicarboxylic acid anhydride 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 β-烟酰胺腺嘌呤二核苷酸 、 氢溴酸 、 三正丁基氢锡 、 聚甘氨酸 、 2,6-蒽二酚 作用下， 以 苯 为溶剂， 反应 100.0h， 生成 (+/-)-cis-1-carbomethoxy-2-methylcyclopentane
  参考文献：
  名称：

  Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols

  摘要：

  DOI：

  10.1021/ja00381a024

文献信息

• DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
  申请人：ALTENBURGER Jean-Michel

  公开号：US20110294788A1

  公开（公告）日：2011-12-01

  The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.

  本发明涉及新型取代二氢吡唑酮衍生物，其制备以及作为转录因子HIF激活剂的治疗用途。
• Heterobicyclic metalloprotease inhibitors
  申请人：Bluhm Harald

  公开号：US20080221092A1

  公开（公告）日：2008-09-11

  The present invention relates generally to amide containing heterobicyclic containing pharmaceutical agents, and in particular, to amide containing heterobicyclic metalloprotease inhibiting compounds. More particularly, the present invention provides a new class of heterobicyclic MMP-3 and/or MMP-13 inhibiting compounds that exhibit an increased potency and selectivity in relation to currently known MMP-13 and MMP-3 inhibitors.

  本发明通常涉及含有酰胺的杂双环含有药物作用的化合物，特别地，涉及含有酰胺的杂双环金属蛋白酶抑制剂。更具体地，本发明提供了一类新型的杂双环MMP-3和/或MMP-13抑制剂化合物，相对于目前已知的MMP-13和MMP-3抑制剂，这些化合物表现出更高的效力和选择性。
• A Model Study of Intramolecular Asymmetric Radical Cyclizations of α-Ester and α-Amide Radicals
  作者：Ru-Long Yeh、Weir-Tom Jiaang、Yeun-Min Tsai

  DOI：10.1002/jccs.199700039

  日期：1997.6

  AbstractStarting from malonate, a practical route was developed for the synthesis of α‐phenylthio acid 3. Several chiral compounds including (‐)‐menthol, (‐)‐8‐pbenylmenthol and a camphor based oxazolidinone 8 reacted with 3 to give α‐phenylthio esters or amide. These sulfides cyclized efficiently when reacted with tributyltin hydride. Among the chiral auxiliaries used, 8‐phenylmenthyl group displayed moderate asymmetric induction (64% ee for cis‐product and 40% ee for trans‐product). Based on this results, a transition state model was proposed to explain the observed stereoselectivity. In this model, due to π,π‐orbital overlap of the phenyl ring and the carbonyl, the si‐face of the most stable conformer of the radical was shielded. This controlled the carbon‐carbon bond formation to occur from the re‐face.
• Canonne, P.; Plamondon, J., Canadian Journal of Chemistry, 1989, vol. 67, p. 555 - 564
  作者：Canonne, P.、Plamondon, J.

  DOI：——

  日期：——
• Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase.
  作者：Eric J. Toone、J.Bryan Jones

  DOI：10.1016/s0957-4166(00)82360-5

  日期：1991.1

  Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of greater-than-or-equal-to 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexane acids being of the opposite absolute configuration types, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22% ee. This stereoselectivity reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.