(+/-)-erythro-2-methyl-3-phenyl-butyric acid | 19731-91-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+/-)-erythro-2-methyl-3-phenyl-butyric acid
• 英文别名: (+/-)-erythro-2-Methyl-3-phenyl-buttersaeure；threo-α-Methyl-β-phenyl-buttersaeure；threo-2-Methyl-3-phenylbuttersaeure；2-Methyl-3-phenylbuttersaeure；(2R,3R)-2-methyl-3-phenylbutanoic acid
• CAS: 19731-91-0；42879-15-2；42971-03-9；121560-21-2；121560-22-3；121651-46-5
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: NRYIIIVJCVRSSH-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  (+/-)-erythro-2-methyl-3-phenyl-butyric acid 在 氢氟酸 作用下， 生成 trans-3,4-Dimethyl-1,2,3,4-tetrahydro-1-naphthalene
  参考文献：
  名称：

  731.差向异构二氢芳烃：顺式-和反式-1,2-二氢-1,2-二甲基萘和9,10-二氢-9,10-二甲基蒽的立体定向合成

  摘要：

  DOI：

  10.1039/jr9620003776
• 作为产物：
  描述：

  ethyl 2-methyl-3-phenyl-3-butenoate 生成 (+/-)-erythro-2-methyl-3-phenyl-butyric acid
  参考文献：
  名称：

  Lead tetraacetate oxidations of stereoisomeric 2-methyl-3-phenylbutyric acids

  摘要：

  DOI：

  10.1021/jo00916a006

文献信息

• Highly Efficient Enantioselective Synthesis of Optically Active Carboxylic Acids by Ru(OCOCH₃)₂[(<i>S</i>)-H₈-BINAP]
  作者：Toshitsugi Uemura、Xiaoyoung Zhang、Kazuhiko Matsumura、Noboru Sayo、Hidenori Kumobayashi、Tetsuo Ohta、Kyoko Nozaki、Hidemasa Takaya

  DOI：10.1021/jo960426p

  日期：1996.1.1

  In the presence of a catalytic amount of Ru(OCOCH3)(2)[(S)-H-8-BINAP] [HB-BINAP = 2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphtyl], the asymmetric hydrogenation of alpha,beta- and beta,gamma-unsaturated carboxylic acids afforded the corresponding saturated carboxylic acids in higher enantiomeric excesses and at faster reaction rates than those using the Ru(OCOCH3)(2)[(R)-BINAP] catalyst [BINAP = 2,2'-bis(diphenylphosphino)-1, 1'-binaphthyl]. The hydrogenation of (E)-2-alkyl-2-alkenoic acids by the H-8-BINAP catalyst system produced saturated acids in 95-97% ee. 2-Methylcinnamic acid was treated with H-8-BINAP-Ru(II) complex as a catalyst to yield a hydrogenated product in much higher ee than that produced by BINAP-Ru(II) (89 and 30% ee, respectively). This homogeneous catalysis using H-8-BINAP-Ru(II) established a promising synthetic route to (S)-ibuprofen in up to 97% ee. Asymmetric hydrogenation of beta-disubstituted acrylic acids also proceeded smoothly with good enantioselectivities (70-93% ee). In addition, the hydrogenation of trisubstituted acrylic acids (up to 88% ee) was investigated. Hydrogen pressure effect on the sense and level of enantioselection was shown to be substrate dependent. The difference between the H-8-BINAP- and BINAP-Ru(II) complexes was also discussed.
• Enantiomerically Pure <i>trans</i>-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1021/ol9910565

  日期：1999.11.1

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.
• LIEBESKIND, L. S.;WELKER, M. E., TETRAHEDRON LETT., 1985, 26, N 26, 3079-3082
  作者：LIEBESKIND, L. S.、WELKER, M. E.

  DOI：——

  日期：——
• HERPES RIBONUCLEOTIDE REDUCTASE INHIBITORS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP0837845B1

  公开（公告）日：2001-11-28
• US5672586A
  申请人：——

  公开号：US5672586A

  公开（公告）日：1997-09-30