(-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol | 82425-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol
• 英文别名: (1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-1-(2-hydroxyethyl)cyclopropane；1-((1S,3R)-3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl)propan-2-one；1-[(1S,2R)-2-(2-hydroxyethyl)-3,3-dimethylcyclopropyl]propan-2-one；2,2-dimethyl-3-(2-hydroxyethyl)-1-(2-oxopropyl)-cis-cyclopropane；1-[(1S,3R)-3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl]propan-2-one
• CAS: 82425-89-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: DJDGXAJVJZDSHK-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  (-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol 在 吡啶 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 96.0h， 生成 (1R,13R,15S,29S)-14,14,17,27,30,30-hexamethyl-4,10-dioxa-18,19,25,26-tetraazatricyclo[27.1.0.013,15]-triaconta-17,26-diene-5,9,20,24-tetraone
  参考文献：
  名称：

  Synthesis of macrocyclic azino and dihydrazido diesters by consecutive [2 + 1]- and [1 + 1]-condensations

  摘要：

  Efficient procedures for the synthesis of 21-24- and 28-31-membered macrocyclic azino diesters and dihydrazido diesters were developed starting from L-menthol, Delta(3)-carene, (+)-alpha-pinene, tetrahydropyran, and 4-methyltetrahydropyran. The key steps in these syntheses were consecutive [2 + 1]- and [1 + 1]-condensations. The 31-membered dihydrazido diester exhibited strong antibacterial activity.

  DOI：

  10.1134/s1070428011090260
• 作为产物：
  描述：

  (1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯 在 lithium aluminium tetrahydride 、 吡啶盐酸盐 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 (-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol
  参考文献：
  名称：

  Baker's yeast-induced asymmetric reduction of the keto group activated by the cyclopropane unit.

  摘要：

  Certain cis-3-substituted 2,2-dimethyl-1-(2-oxopropyl)-cyclopropanes are effectively reduced by baker's yeast to give predominantly (s)-isomers of the corresponding 2-hydroxypropyl derivatives. Reduction of the 2-oxopropyl group proceeds more rapidly (ca. 3.5 times) and with higher stereoselectivity [(S):(R) = 98:2] when the group is attached to the (s)-carbon of the cyclopropane unit than of the keto group attached to the (R)-carbon [(S):(R) = (88):(12)]. Yeast reduction of the keto derivatives is effectively carried out when substituents at C-3 are as follows: CH2COOCH3, -CH2COCH3, -CN, -CH2CN, -CH2CH2OH, and the relative rates of reduction are 36:36:15:13:7. No reduction occurs when substituents at C-3 are propyl, 2-methyl-2-hydroxypropyl or 2-methyl-1,3-dioxolan-2-yl methyl groups.

  DOI：

  10.1016/s0957-4166(00)82103-5

文献信息

• SELECTIVE HYDROGENATION OF ALDEHYDE WITH RU/BIDENTATE LIGANDS COMPLEXES
  申请人：FIRMENICH SA

  公开号：US20140243526A1

  公开（公告）日：2014-08-28

  The present invention relates to processes for the reduction by hydrogenation, using molecular H 2 , of a C 5 -C 20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N 2 P 2 O 2 , wherein the coordinating atoms N 2 are provided by a first bidentate ligand, the coordinating atoms P 2 are provided by a second bidentate ligand and the coordinating atoms O 2 are provided by two non-linear carboxylate ligands; and —optionally of an acidic additive.

  本发明涉及利用分子H2对含有一个或两个醛基官能团的C5-C20底物进行加氢还原的过程，将其转化为相应的醇或二醇，其特征在于所述过程在以下条件下进行：—至少一种催化剂或前驱体存在，其形式为具有N2P2O2配位球的钌配合物，其中配位原子N2由第一双齿配体提供，配位原子P2由第二双齿配体提供，配位原子O2由两个非线性羧酸盐配体提供；和—可选地加入酸性添加剂。
• Ruthenium-Catalyzed Highly Chemoselective Hydrogenation of Aldehydes
  作者：Lucia Bonomo、Laurent Kermorvan、Philippe Dupau

  DOI：10.1002/cctc.201500006

  日期：2015.3

  [dppe=1,2‐bis(diphenylphosphino)ethane] complex under base‐free conditions allowed highly efficient and selective hydrogenation of aldehydes in the presence of ketones in addition to olefins. Even in the case of highly sensitive 1,6‐ketoaldehydes, the desired ketoalcohols were obtained in high yields with 94–99 % overall selectivity at complete aldehyde conversion with a TON up to 30 000. The lack of requirement

  在无碱条件下使用[（乙二胺）（dppe）Ru（OCO t Bu）2 ] [dppe = 1,2-双（二苯基膦基）乙烷]配合物可以在存在下列条件的情况下对醛进行高效和选择性的加氢除烯烃外的酮。即使在高度敏感的1,6-酮醛的情况下，也可以在高醛的情况下以高达30000 TON的总醛转化率获得高产率，94-99％的总选择性的酮醇。对强碱性助催化剂的需求不足极性溶剂和质子传递溶剂还可以有效且高度化学选择性地还原带有其他官能团的醛，例如环氧化物，羧酸，酯，酰胺和腈，从而强调了催化剂的潜在合成用途。
• Selective hydrogenation of aldehyde with ru/bidentate ligands complexes
  申请人：FIRMENICH SA

  公开号：US09090534B2

  公开（公告）日：2015-07-28

  The present invention relates to processes for the reduction by hydrogenation, using molecular H2, of a C5-C20 substrate containing one or two aldehydes functional groups into the corresponding alcohol or diol, characterized in that said process is carried out in the presence of —at least one catalyst or pre-catalyst in the form of a ruthenium complex having a coordination sphere of the N2P2O2, wherein the coordinating atoms N2 are provided by a first bidentate ligand, the coordinating atoms P2 are provided by a second bidentate ligand and the coordinating atoms O2 are provided by two non-linear carboxylate ligands; and—optionally of an acidic additive.

  本发明涉及使用分子氢进行还原的C5-C20底物的过程，该底物含有一个或两个醛官能团，并转化为相应的醇或二元醇。其特征在于，在至少一种催化剂或前催化剂的存在下进行该过程，所述催化剂或前催化剂以N2P2O2的配位球形形式存在，其中协同原子N2由第一双齿配体提供，协同原子P2由第二双齿配体提供，协同原子O2由两个非线性羧酸盐配体提供；以及可选的酸性添加剂。
• Satoh, Tsuyoshi; Kaneko, Youhei; Okuda, Teruyoshi, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 9, p. 3452 - 3460
  作者：Satoh, Tsuyoshi、Kaneko, Youhei、Okuda, Teruyoshi、Uwaya, Satoru、Yamakawa, Koji

  DOI：——

  日期：——
• Kula, J.; Sikora, M., Polish Journal of Chemistry, 1994, vol. 68, # 9, p. 1699 - 1706
  作者：Kula, J.、Sikora, M.

  DOI：——

  日期：——