(2S)-2-(3-methoxyphenyl)propanal

• 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: (2S)-2-(3-methoxyphenyl)propanal
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: FMKPGKIYGGLNNJ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methoxy-α-methylstyrene oxide 在 (S)-6,6'-bis(2,4,6-triisopropylphenyl)-1,1'-spirobiindan-yl-7,7'-diylhydrogen-N-triflyl phosphoramide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 以37%的产率得到
  参考文献：
  名称：

  手性布朗斯台德酸催化外消旋环氧化物的不对称重排†

  摘要：

  本文描述了一种手性布朗斯台德酸通过氢转移工艺催化外消旋环氧化物的不对称1,2-重排合成手性醛，然后进行还原反应，可以以适度的收率提供各种旋光性醇，高达50％ee。特别地，还已经实现了通过连续的环氧化，重排和还原直接从简单的烯烃简单地一锅法合成手性醇。

  DOI：

  10.1039/c3ob27285k

文献信息

• Enantioselective Hydroformylation by a Rh-Catalyst Entrapped in a Supramolecular Metallocage
  作者：Cristina García-Simón、Rafael Gramage-Doria、Saeed Raoufmoghaddam、Teodor Parella、Miquel Costas、Xavi Ribas、Joost N. H. Reek

  DOI：10.1021/ja512637k

  日期：2015.2.25

  Regio- and enantioselective hydroformylation of styrenes is attained upon embedding a chiral Rh complex in a nonchiral supramolecular cage formed from coordination-driven self-assembly of macrocyclic dipalladium complexes and tetracarboxylate zinc porphyrins. The resulting supramolecular catalyst converts styrene derivatives into aldehyde products with much higher chiral induction in comparison to the nonencapsulated Rh catalyst. Spectroscopic analysis shows that encapsulation does not change the electronic properties of the catalyst nor its first coordination sphere. Instead, enhanced enantioselectivity is rationalized by the modification of the second coordination sphere occurring upon catalyst inclusion inside the cage, being one of the few examples in achieving an enantioselective outcome via indirect through-space control of the chirality around the catalyst center. This effect resembles those taking place in enzymatic sites, where structural constraints imposed by the enzyme cavity can impart stereoselectivities that cannot be attained in bulk. These results are a showcase for the future development of asymmetric catalysis by using size-tunable supramolecular capsules.