(+/-)-3t-(α-hydroxy-isobutyryl)-2,2-dimethyl-cyclopropane-r-carboxylic acid | 713-27-9

• 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: (+/-)-3t-(α-hydroxy-isobutyryl)-2,2-dimethyl-cyclopropane-r-carboxylic acid
• 英文别名: (+/-)-3t-(α-Hydroxy-isobutyryl)-2,2-dimethyl-cyclopropan-r-carbonsaeure；(+/-)-2,2-Dimethyl-3-(1'-oxo-2'-hydroxy-2'-methyl-propyl)-1,3-trans-cyclopropancarbonsaeure-(1), (+/-)-Ketol-chrysanthemsaeure；(+/-)-2,2-Dimethyl-trans-3-(1-oxo-2-hydroxy-2-methyl-propyl)-cyclopropan-1-carbonsaeure, (+/-)-trans-Ketol-chrysanthemsaeure；(+/-)-2,2-Dimethyl-3-(1'-oxo-2'-hydroxy-2'-methyl-propyl)-1,3-trans-cyclopropan-1-carbonsaeure, Ketol-chrysanthemsaeure；(+/-)-2,2-Dimethyl-3-(1'-oxo-2'-hydroxy-2'-methyl-propyl)-1,3-trans-cyclopropancarbonsaeure-(1)；(+/-)-2,2-Dimethyl-3-trans-(1'-oxo-2'-hydroxy-2'-methyl-propyl)-cyclopropan-1-carbonsaeure；(1R,3R)-3-(2-Hydroxy-2-methylpropanoyl)-2,2-dimethylcyclopropane-1-carboxylic acid
• CAS: 713-27-9；2717-17-1；3858-41-1；17779-26-9；92016-17-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: BQOZTZVUESCLBP-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3t-(α-hydroxy-isobutyryl)-2,2-dimethyl-cyclopropane-r-carboxylic acid 在 sodium tetrahydroborate 、 三甲氧基磷 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 31.5h， 生成 methyl (dl)-trans-chrysanthemate
  参考文献：
  名称：

  Novel synthesis of (d,l) trans-chrysanthemic acid involving a β-diketone fragmentation

  摘要：

  Methyl (d,l) trans-chrysanthemate as well as its cis-diastereoisomer have been prepared from dimethyl dimedone, one of their isomers, in a few steps and with complete control of the relative stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01270-4
• 作为产物：
  描述：

  2,2,5,5-四甲基环己烷-1,3-二酮 在 lithium hydroxide 、 potassium tert-butylate 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (+/-)-3t-(α-hydroxy-isobutyryl)-2,2-dimethyl-cyclopropane-r-carboxylic acid
  参考文献：
  名称：

  Novel synthesis of (d,l) trans-chrysanthemic acid involving a β-diketone fragmentation

  摘要：

  Methyl (d,l) trans-chrysanthemate as well as its cis-diastereoisomer have been prepared from dimethyl dimedone, one of their isomers, in a few steps and with complete control of the relative stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01270-4

文献信息

• Cyclopropane cleavage of chrysanthemic acid relatives to santolinyl, artemisyl, and lavandulyl structures: acid-catalysed and biosynthetic experiments
  作者：L. Crombie、Patricia A. Firth、R. P. Houghton、D. A. Whiting、D. K. Woods

  DOI：10.1039/p19720000642

  日期：——

  compounds undergo acid-catalysed 1,2-cyclopropane (santolinyl) scission; on the other hand, 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropylmethanol (chrysanthemyl alcohol) and various similar compounds undergo 1,3-(artemisyl) cleavage. Introduction of functional groups into the methylpropenyl side-chain in chrysanthemic-type structures allows acid-catalysed cleavage by a 2,3-(lavandulyl) pathway. Certain

  3-异丁基-2,2-二甲基环丙基甲醇（二氢菊花烷醇）和相关化合物经历了酸催化的1,2-环丙烷（Santolinyl）裂解；另一方面，2，2-二甲基-3-（2-甲基丙烯基）-环丙基甲醇（菊花醇）和各种类似的化合物经历1，3-（蒿甲酰基）裂解。在菊类结构的甲基丙烯基侧链中引入官能团可通过2，3-（lavandulyl）途径进行酸催化裂解。某些反应对于用不规则无环萜烯单元进行烷基化以及生物合成工作中的特定原子分离而言可能是有用的。
• Matsui et al., Journal of the Agricultural Chemical Society of Japan, 1956, vol. 20, p. 89,91
  作者：Matsui et al.

  DOI：——

  日期：——
• Chemoenzymatic synthesis of enantiopure geminally dimethylated cyclopropane-based C2- and pseudo-C2-symmetric diamines
  作者：Guo-Qiang Feng、De-Xian Wang、Qi-Yu Zheng、Mei-Xiang Wang

  DOI：10.1016/j.tetasy.2006.10.030

  日期：2006.10

  Enantiopure (-)-(1S,3S)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanecarboxamide 2 and (+)-(1R,3R)-2,2-dimethyl-3(2-methylprop-l-enyl)cyclopropanecarboxylic acid 3 were easily obtained from a multigram scale biotransformation of racemic amide or nitrile in the presence of Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions. Coupled with efficient and convenient chemical manipulations, comprising mainly of the Curtius rearrangement, oxidation, and reduction reactions, chiral C-2-symmetric (1S,2S)-3,3-dimethylcyclopropane-1,2-diamine 6 and ((1R,3R)-3-(aminomethyl)-2,2-dimethylcyclopropyl)methanamine 8 and pseudo-C-2-symmetric (1S,3S)-3-(aminomethyl)-2,2-dimethylcyclopropanamine 11 were prepared. These were also transformed into the corresponding chiral salen derivatives 12, 13, and 14, respectively, in almost quantitative yields. (c) 2006 Elsevier Ltd. All rights reserved.