(1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde | 871468-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde
• 英文别名: Cyclopentanecarboxaldehyde, 2-(2-oxo-2-phenylethyl)-, (1S,2S)-；(1S,2S)-2-phenacylcyclopentane-1-carbaldehyde
• CAS: 871468-89-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: SNBLDCSKJDOITF-QWHCGFSZSA-N

物化性质

• 沸点：
  344.3±15.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 0.17h， 生成 (1R,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarboxylic acid
  参考文献：
  名称：

  Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction

  摘要：

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.

  DOI：

  10.1021/ja055740s
• 作为产物：
  描述：

  1,6-己二醇 在 碳酸氢钠 吡啶 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 (4R)-N-(naphthyl)-2,2-Me₂-thiazolidine-4-carboxamide trifluoroacetate 、 乙酸酐 、 对甲苯磺酸 、 potassium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 79.0h， 生成 (1S,2S)-2-(2-oxo-2-phenylethyl)-cyclopentanecarbaldehyde
  参考文献：
  名称：

  Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction

  摘要：

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.

  DOI：

  10.1021/ja055740s

文献信息

• Asymmetric Intramolecular Michael Reaction Catalyzed by Proline-Derived Small Anilides
  作者：Hisao Nishiyama、Makoto Kikuchi、Tomohiko Inagaki

  DOI：10.1055/s-2007-977421

  日期：2007.4

  Simple proline-derived anilide-catalyzed asymmetric -intramolecular Michael reaction was described. Chiral cyclic keto-aldehydes were obtained from acyclic formyl enones in excellent yields with good stereoselectivity. The reaction proceeded in exceptionally fast with a commercially available proline anilide. On the other hand, the longer reaction time conduced toward the higher -diastereoselectivity

  描述了简单的脯氨酸衍生的苯胺催化的不对称分子内迈克尔反应。手性环状酮醛是从无环甲酰基烯酮以优异的收率和良好的立体选择性获得的。使用市售的脯氨酸苯胺，反应进行得异常快。另一方面，通过环状酮醛的有利异构化，较长的反应时间有助于更高的非对映选择性。
• Catalytic Asymmetric Reductive Michael Cyclization
  作者：Jung Woon Yang、Maria T. Hechavarria Fonseca、Benjamin List

  DOI：10.1021/ja055735o

  日期：2005.11.1

  reduction-Michael cyclization of enal enones has been developed. Accordingly, treating the enal enone with a Hantzsch dihydropyridine in the presence of a catalytic amount of an imidazolidinone organocatalyst provides cyclic keto aldehydes in high yields and enantiomeric excesses. The reaction works well with aliphatic and aromatic substrates in the synthesis of five- and six-membered carbacyclic derivatives.

  已经开发了一种高效的化学、区域、非对映选择性和对映选择性有机催化串联共轭还原 - 烯酮的迈克尔环化。因此，在催化量的咪唑啉酮有机催化剂存在下用Hantzsch二氢吡啶处理烯醛以高产率和对映体过量提供环状酮醛。在合成五元和六元碳环衍生物时，该反应与脂肪族和芳香族底物反应良好。
• Cysteine-Derived Organocatalyst in a Highly Enantioselective Intramolecular Michael Reaction
  作者：Yujiro Hayashi、Hiroaki Gotoh、Tomohiro Tamura、Hirofumi Yamaguchi、Ryouhei Masui、Mitsuru Shoji

  DOI：10.1021/ja055740s

  日期：2005.11.23

  Asymmetric intramolecular Michael reaction catalyzed by an organocatalyst derived from cysteine has been developed for the synthesis of chiral bicyclo[4.3.0]nonene and cis-disubstituted cyclopentane skeletons with a creation of three or two contiguous chiral centers in good yield with high diastereo- and excellent enantioselectivities.