Oxiranecarboxaldehyde, 3-(4-methylphenyl)-, (2R,3S)-rel- | 97985-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Oxiranecarboxaldehyde, 3-(4-methylphenyl)-, (2R,3S)-rel-
• 英文别名: (2R,3S)-3-(4-methylphenyl)oxirane-2-carbaldehyde
• CAS: 97985-67-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: NEHNWNKOQANMTK-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Oxiranecarboxaldehyde, 3-(4-methylphenyl)-, (2R,3S)-rel- 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 ((2S,3S)-3-(p-tolyl)oxiran-2-yl)methanol
  参考文献：
  名称：

  Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

  摘要：

  The asymmetric epoxidation of alpha,beta-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.009
• 作为产物：
  描述：

  p-Methyl-zimtaldehyd 在 (5R,6R)-6-((tert-butyldiphenylsilyl)oxy)-1-azaspiro[4.4]nonane 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 48.17h， 以96%的产率得到
  参考文献：
  名称：

  Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

  摘要：

  The asymmetric epoxidation of alpha,beta-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.009

文献信息

• Nanosheet-enhanced efficiency in amine-catalyzed asymmetric epoxidation of α, β-unsaturated aldehydes via host-guest synergy
  作者：Hui Liu、Zhe An、Jing He

  DOI：10.1016/j.mcat.2017.09.035

  日期：2017.12

  Amine-catalyzed asymmetric epoxidation of α, β-unsaturated aldehydes has been promoted by attaching the nanosheets of layered double hydroxides (LDHs), a natural and/or synthetic anionic layered compound. 76% of epoxide yield and 93% ee of major diastereomer have been afforded in the asymmetric epoxidation of cinnamaldehyde. The amine sites employed here are the amino group in α-amino acid anion intercalated

  胺催化的α，β不对称环氧化通过附着层状双氢氧化物（LDH）的纳米片（天然和/或合成阴离子层状化合物），可以促进不饱和醛的形成。肉桂醛的不对称环氧化提供了76％的环氧化物收率和93％ee的主要非对映异构体。这里使用的胺位点是插入在LDHs的层间空间中的α-氨基酸阴离子中的氨基。已经揭示出LDHs的纳米片通过提供所需的碱性和通过用作氨基酸的刚性取代基而在催化活性的增强中起关键作用。疏水层间微环境和插层氨基酸阴离子的有序排列另外有助于催化效力。
• Highly Diastereoselective Formation of 1,2,3-Trisubstituted Cyclopropane Derivatives
  作者：Xingang Xie、Guoren Yue、Shouchu Tang、Xing Huo、Qiren Liang、Xuegong She、Xinfu Pan

  DOI：10.1021/ol051653t

  日期：2005.9.1

  A highly diastereoselective formation of cyclopropane derivatives was reported. When the chiral phenylvinyl epoxide reacted with lithiated 2-alkyl-1,3-dithiane or lithiated alkyl carbonanion in the presence of HMPA, cyclopropanes bearing stereochemistry at all three positions on the ring were readily obtained in high yields of 80-97% and high dr values of 68:32-99:1. This reaction was supposed to be

  据报导，环丙烷衍生物具有高度非对映选择性。当在HMPA存在下，手性苯基乙烯基环氧化物与锂化的2-烷基-1,3-二硫杂环丁烷或锂化的烷基碳阴离子反应时，可轻松获得环上所有三个位置均具有立体化学结构的环丙烷，产率高，可达80-97％ dr值为68：32-99：1。该反应被认为是串联共轭加成-环氧打开顺序。[反应：看文字]
• Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals
  作者：Xingwang Wang、Benjamin List

  DOI：10.1002/anie.200704185

  日期：2008.1.25
• Revinskii, I. F.; Tishchenko, I. G.; Burd', V. N., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, p. 637 - 641
  作者：Revinskii, I. F.、Tishchenko, I. G.、Burd', V. N.、Bubel', O. N.

  DOI：——

  日期：——