(S)-Butylsuccinic acid | 63163-09-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-Butylsuccinic acid
• 英文别名: (S)-(-)-n-butylsuccinic acid；(S)-(-)-2-butylbutanedioic acid；S-(-)-α-Butylbernsteinsaeure；(2S)-2-butylbutanedioic acid
• CAS: 63163-09-7
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: WOPLHDNLGYOSPG-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-Butylsuccinic acid 、 苯胺 生成 (S)-2-Butyl-N¹,N⁴-diphenyl-succinamide
  参考文献：
  名称：

  SHAO, LIMING;MIYATA, SHIRO;MURAMATSU, HITOSHI;KAWANO, HIROYUKI;ISHII, YOU+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1441-1445

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(+)-3-(nitromethyl)heptanoic acid 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 (S)-Butylsuccinic acid
  参考文献：
  名称：

  A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

  摘要：

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.014

文献信息

• Asymmetric synthesis of (R)- and (S)-4-(substituted benzyl)dihydrofuran-2(3H)-ones: an application of the ruthenium-binap complex-catalysed asymmetric hydrogenation of alkylidenesuccinic acids
  作者：Liming Shao、Shiro Miyata、Hitoshi Muramatsu、Hiroyuki Kawano、Youichi Ishii、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1039/p19900001441

  日期：——

  A concise synthesis of (S)- or (R)-4-(substituted benzyl)dihydrofuran-2(3H)-ones (1) with high enantiomeric purity is presented. (S)- or (R)-(Substituted benzyl)succinic acids (6) 97% enantiomeric excess) were first prepared by Ru2Cl4[(R)- or (S)-binap)]2(NEt3) catalysed asymmetric hydrogenation of (substituted benzylidene)succinic acids. The diacids (6) were converted into (R)- or (S)-2-(substituted

  提出了具有高对映体纯度的（S）-或（R）-4-（取代的苄基）二氢呋喃-2（3 H）-ones（1）的简明合成方法。首先通过Ru 2 Cl 4 [（R）-或（S）-binap）] 2（NEt 3）催化制备（S）-或（R）-（取代的苄基）琥珀酸（6），对映体过量97％）。 （取代的亚苄基）琥珀酸的不对称氢化。将二酸（6）转化为（R）-或（S）-2-（取代的苄基）丁烷-1,4-二醇（9）和随后的RuH 2（PPh 3）4催化的（9）脱氢内酯化反应，得到内酯（1），其手性构型完全保留中心。
• Enantioselective Carbometalation of Cinnamyl Derivatives: New Access to Chiral Disubstituted Cyclopropanes— Configurational Stability of Benzylic Organozinc Halides
  作者：Stephanie Norsikian、Ilan Marek、Sophie Klein、Jean F. Poisson、Jean F. Normant

  DOI：10.1002/(sici)1521-3765(19990702)5:7<2055::aid-chem2055>3.0.co;2-9

  日期：1999.7.2
• Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer’s sultam
  作者：Gary P. Reid、Kieron W. Brear、David J. Robins

  DOI：10.1016/j.tetasy.2003.12.010

  日期：2004.3

  Conjugate addition of Grignard reagents to N,N'-fumaroylbis[(2R)-bornane-10,2-sultam] 1 occurred with moderate to high levels of diastereoselectivity. Diastereomeric excesses were estimated by analysis of the H-1 NMR spectra of the succinamide mixtures and enantiomeric excesses from F-19 NMR spectra of the bis Mosher esters of the diols produced by reductive cleavage of the succinamides. Saponification of the succinamides gave the corresponding (R)-succinic acids with ees up to 92% showing that addition of the Grignard reagents takes place selectively on the re-face of 1. (C) 2003 Elsevier Ltd. All rights reserved.
• ZHOU, BO;XU, YUANYAO, J. ORG. CHEM., 53,(1988) N 18, C. 4419-4421
  作者：ZHOU, BO、XU, YUANYAO

  DOI：——

  日期：——
• Prostaglandin analogues, processes for their preparation and pharmaceutical compositions containing them
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0196380B1

  公开（公告）日：1991-09-18