trans-3-t-butylcyclopentanecarboxylic acid

• 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: trans-3-t-butylcyclopentanecarboxylic acid
• 英文别名: (1R,3R)-3-tert-butylcyclopentane-1-carboxylic acid
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD28145570
• 分子量: 170.252
• InChiKey: IXNHRYIEXFPMQW-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  trans-3-t-butylcyclopentanecarboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-(TERT-BUTYL)-1-(MESITYLMETHYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID
  参考文献：
  名称：

  Cooper, Catherine N.; Jenner, Peter J.; Perry, Nigel B., Journal of the Chemical Society. Perkin transactions II, 1982, p. 605 - 612

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(叔丁基)环己酮 在 thallium(III) nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以65%的产率得到trans-3-t-butylcyclopentanecarboxylic acid
  参考文献：
  名称：

  Thallium trinitrate mediated ring contraction of monocyclic ketones: Stereochemical aspects

  摘要：

  The reaction of 3- and 4-alkylcyclohexanones with thallium trinitrate (TTN) leads to the alkylcyclopentanecarboxylic acids in good yields and with high degree of stereoselectivity. The ring contraction of 2-methylcyclohexanone gives poor yields and 2,6-dimethylcyclohexanone does not undergo contraction. The observed diastereoselectivities of the reactions agree with the mechanism proposed by McKillop et al. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00246-3

文献信息

• Gream,G.E. et al., Australian Journal of Chemistry, 1978, vol. 31, p. 835 - 862
  作者：Gream,G.E. et al.

  DOI：——

  日期：——
• Cooper, Catherine N.; Jenner, Peter J.; Perry, Nigel B., Journal of the Chemical Society. Perkin transactions II, 1982, p. 605 - 612
  作者：Cooper, Catherine N.、Jenner, Peter J.、Perry, Nigel B.、Russel-King, Jonquil、Storesund, Hans J.、Whiting, Mark C.

  DOI：——

  日期：——
• Thallium trinitrate mediated ring contraction of monocyclic ketones: Stereochemical aspects
  作者：Helena M.C. Ferraz、Luiz F. Silva

  DOI：10.1016/s0040-4039(97)00246-3

  日期：1997.3

  The reaction of 3- and 4-alkylcyclohexanones with thallium trinitrate (TTN) leads to the alkylcyclopentanecarboxylic acids in good yields and with high degree of stereoselectivity. The ring contraction of 2-methylcyclohexanone gives poor yields and 2,6-dimethylcyclohexanone does not undergo contraction. The observed diastereoselectivities of the reactions agree with the mechanism proposed by McKillop et al. (C) 1997 Elsevier Science Ltd.