(+/-)-2-<2-Hydroxy-2-methyl-propyl>-3,3-dimethyl-cyclopropancarbonsaeure; ((+/-)-trans-Dihydro-hydroxy-chrysanthemumsaeure)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-2-<2-Hydroxy-2-methyl-propyl>-3,3-dimethyl-cyclopropancarbonsaeure; ((+/-)-trans-Dihydro-hydroxy-chrysanthemumsaeure)
• 英文别名: (+/-)-trans-Dihydro-2'-hydroxy-chrysanthemsaeure；(+/-)-3t-(β-hydroxy-isobutyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid；(+/-)-3t-(β-Hydroxy-isobutyl)-2,2-dimethyl-cyclopropan-r-carbonsaeure；(1R,3R)-3-(2-hydroxy-2-methylpropyl)-2,2-dimethylcyclopropane-1-carboxylic acid
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: YFMRCDOGWGYUGF-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-<2-Hydroxy-2-methyl-propyl>-3,3-dimethyl-cyclopropancarbonsaeure; ((+/-)-trans-Dihydro-hydroxy-chrysanthemumsaeure) 在 对甲苯磺酸 作用下， 生成 (+)-反式-菊酸
  参考文献：
  名称：

  Matsui; Miyano, Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 159

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-二氢-5,5-二甲基-4-(2-甲基-1-丙烯基)呋喃-2(3H)-酮 生成 (+/-)-2-<2-Hydroxy-2-methyl-propyl>-3,3-dimethyl-cyclopropancarbonsaeure; ((+/-)-trans-Dihydro-hydroxy-chrysanthemumsaeure)
  参考文献：
  名称：

  Julia,M. et al., Bulletin de la Societe Chimique de France, 1965, p. 1014 - 1019

  摘要：

  DOI：

文献信息

• 948. Synthesis, absolute configuration, and ring-fission of cis- and trans-homocaronic acid: their configurative relation to natural terpenes
  作者：L. Crombie、J. Crossley、D. A. Mitchard

  DOI：10.1039/jr9630004957

  日期：——
• The chrysanthemumcarboxylic acids. V.—hydration of the chrysanthemic acids
  作者：S. H. Harper、R. A. Thompson

  DOI：10.1002/jsfa.2740030508

  日期：1952.5

  AbstractIn boiling dilute sulphuric acid hydration of (±)‐trans‐chrysanthemic acid occurs to give the crystalline (±)‐trans‐δ‐hydroxydihydrochrysanthemic acid. In like manner (+)‐and (‐)‐trans‐chrysanthemic acids yield the crystalline (‐)‐ and (+)‐trans‐δ‐hydroxy‐dihydrochrysanthemic acids respectively. No racemization occurs as the recovered ( + )‐and ( ‐ )‐trans‐chrysanthemic acids have unchanged specific rotation.The lactonization of (±)‐cis‐chrysanthemic acid to (±)‐cis‐dihydrochrysanthemo‐δ‐lactone in boiling dilute sulphuric acid is shown to be reversible and to constitute an example of lacto‐enoic tautomerism. ( + )‐ and ( ‐ )‐cis‐Chrysanthemic acids are similarly lactonized to the crystalline (+)‐ and (‐)‐cis‐dihydrochrysanthemo‐δ‐lactones. The latter lactone is not identical with (‐)‐pyrocin, whose structure is confirmed as (‐)‐β‐isobutenyliso‐hexano‐γ‐lactone.
• XONDA, TOSIKO;ITATANI, NOBUSIGEH;XORIUTI, TADAU;XIGO, AKIO
  作者：XONDA, TOSIKO、ITATANI, NOBUSIGEH、XORIUTI, TADAU、XIGO, AKIO

  DOI：——

  日期：——
• Julia,M. et al., Bulletin de la Societe Chimique de France, 1965, p. 1014 - 1019
  作者：Julia,M. et al.

  DOI：——

  日期：——
• Matsui; Miyano, Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 159
  作者：Matsui、Miyano

  DOI：——

  日期：——