(R)-2-(3-butoxy-4-methoxybenzyl)-3-methylbutanoic acid | 1421821-94-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-2-(3-butoxy-4-methoxybenzyl)-3-methylbutanoic acid
• 英文别名: (2R)-2-[(3-butoxy-4-methoxyphenyl)methyl]-3-methylbutanoic acid
• CAS: 1421821-94-4
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: KYOSZEVNBPGPBU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-2-(3-butoxy-4-methoxybenzylidene)-3-methylbutanoic acid 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 13-[2-(12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yloxy)-1,2-bis(1,4-dioxaspiro[4.5]decan-3-yl)ethoxy]-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、3.45 MPa 条件下， 反应 24.0h， 以75%的产率得到
  参考文献：
  名称：

  Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes

  摘要：

  A novel catalytic system for the hydrogenation of dimethyl itaconate has been developed by using rhodium-diphosphite complexes. These chiral diphosphite ligands were derived from glucopyranoside, D-mannitol derivatives, and binaphthyl or H-8-binaphthyl phosphochloridites. The ligands based on the methyl 3,6-anhydro-alpha-D-glucopyranoside backbone and (R)- and (S)-binaphthol and/or (R)- and (S)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthol gave almost complete conversion of the dimethyl itaconate and both enantiomers of dimethyl 2-methylsuccinate with excellent enantioselectivities. The stereochemically matched combination of methyl 3,6-anhydro-alpha-D-glucopyranoside and H-8-(S)-binaphthyl in ligand 2,4-bis{[(S)-1,1'-H-8-binaphthyl-2,2'-diyl]-phosphite} methyl 3,6-anhydro-alpha-D-glucopyranoside was essential to afford dimethyl 2-methylsuccinate with up to 98% ee. The sense of the enantioselectivity of products was predominantly determined by the configuration of the biaryl moieties of the ligands. An initial screening of [Rh(cod)(2)]BF4 with these ligands in the hydrogenation of (E)-2-(3-butoxy-4-methoxybenzylidene)-3-methylbutanoic acid was carried out. Good enantioselectivity (75% ee) and low yield for (R)-2-(3-butoxy-4-methoxybenzyl)-3-methylbutanoic acid were obtained. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.001