(S)-2-methyl-4-phenyl-1-butanoic acid | 41927-29-1

• 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: (S)-2-methyl-4-phenyl-1-butanoic acid
• 英文别名: (S)-2-methyl-4-phenyl-1-butyric acid；(2S)-2-methyl-4-phenylbutanoic acid；(S)-2-methyl-4-phenylbutiric acid；2-Methyl-4-phenyl-buttersaeure；(S)-2-methyl-4-phenyl-butyric acid；(S)-2-Methyl-4-phenyl-buttersaeure
• CAS: 41927-29-1
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: OCKZHEXBLOOGOC-VIFPVBQESA-N

物化性质

• 沸点：
  298.3±9.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 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

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-4-phenyl-1-butanoic acid 在 硫酸 、 溶剂黄146 、 铂 作用下， 生成 (S)-2-methyl-4-cyclohexyl-butyric acid ethyl ester
  参考文献：
  名称：

  Levene; Marker, Journal of Biological Chemistry, 1935, vol. 110, p. 311,319

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基-1-丁炔 在 palladium diacetate 、 [RuCl2(benzene)]2 甲烷磺酸 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 50.0 ℃ 、10.13 MPa 条件下， 反应 48.0h， 生成 (S)-2-methyl-4-phenyl-1-butanoic acid
  参考文献：
  名称：

  The asymmetric hydrogenation of 2-phenethylacrylic acid as the key step for the enantioselective synthesis of Citralis Nitrile®

  摘要：

  A catalytic approach to the enantio selective synthesis of Citralis Nitrile((R)) (3-methyl-5-phenyl-pentanenitrile, a citrus-type odorant) is described. The key step is the transition-metal catalyzed asymmetric hydrogenation of 2-phenethylacrylic acid. Among the different catalysts tested, the most efficient appears to be the one formed by combining in situ [Ru(benzene)Cl-2](2) with the atropisomeric diphosphine MeOBIPHEP and triethylamine, which allows us to obtain enantiomeric excesses up to 98% under mild conditions. Very good results (ees > 80%) have also been obtained using iridium cationic complexes in combination with a phosphinooxazoline ligand. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.129

文献信息

• Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel‐Catalyzed Cascade Reactions: Facile Synthesis of Profens
  作者：Peng Yang、Yaxin Sun、Kaiyue Fu、Li Zhang、Guang Yang、Jieyu Yue、Yu Ma、Jianrong Steve Zhou、Bo Tang

  DOI：10.1002/anie.202111778

  日期：2022.1.3

  A simple nickel catalyst converts terminal alkynes and formic acid to α-chiral carboxylic acids in high enantioselectivity. The reaction proceeds via the hydrocarboxylation of alkynes and enantioselective transfer hydrogenation of acrylic acids.

  一种简单的镍催化剂以高对映选择性将末端炔烃和甲酸转化为 α-手性羧酸。该反应通过炔烃的加氢羧化和丙烯酸的对映选择性转移氢化进行。
• [EN] MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS<br/>[FR] COMPOSÉS MACROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DU PROTÉASOME
  申请人：UNIV CORNELL

  公开号：WO2019075259A1

  公开（公告）日：2019-04-18

  The compounds of the present invention are represented by the following compounds having Formula I and Formula (I'): where the substituents R1, R2, R2', R3, R4, R5, R', R", X, Y, and Z are as defined herein and where the substituents R1, R2, R3, R4, R5, R', R", X, Y, and Z are as defined herein. These compounds are used in the treatment of bacterial infections, parasite infections, fungal infections, cancer, immunologic disorders, autoimmune disorders, neurodegenerative diseases and disorders, inflammatory disorders, or muscular dystrophy or for providing immunosuppression for transplanted organs or tissues.

  本发明的化合物由具有以下式I和式(I')的化合物表示，其中取代基R1、R2、R2'、R3、R4、R5、R'、R"、X、Y和Z如本文所定义，取代基R1、R2、R3、R4、R5、R'、R"、X、Y和Z如本文所定义。这些化合物用于治疗细菌感染、寄生虫感染、真菌感染、癌症、免疫紊乱、自身免疫性疾病、神经退行性疾病和紊乱、炎症性疾病，或肌肉萎缩症，或用于为移植的器官或组织提供免疫抑制。
• Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid
  作者：Wenlong Ren、Mingzhou Wang、Jianqiong Guo、Jintao Zhou、Jianxiao Chu、Yuan Shi、Yian Shi

  DOI：10.1021/acs.orglett.1c04231

  日期：2022.1.28

  A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

  描述了用 HCOOH 对末端烯烃进行区域选择性 Pd 催化的加氢羧化反应。在温和的反应条件下，可以很容易地获得具有高区域选择性的多种支链羧酸。该反应操作简单，不需要处理有毒 CO。配体和 LiCl 是反应反应性和选择性的重要因素。
• Highly Diastereoselective Preparation of (<i>E</i>)-Alkenylsilanes Bearing an α-Chiral Center
  作者：Sylvie Perrone、Paul Knochel

  DOI：10.1021/ol063097o

  日期：2007.3.1

  The copper(I)-mediated anti-S(N)2' allylic substitution allows a highly stereoselective preparation of alkenylsilanes bearing a chiral center in the alpha-position with high transfer of chirality. These alkenylsilanes were converted into alpha,beta-unsaturated ketones or into the corresponding boronic esters without loss of the chiral information. [reaction: see text]

  铜（I）介导的抗-S（N）2'的烯丙基取代可以高度立体选择性地制备在α-位带有手性中心的烯基硅烷，且手性转移率很高。在不损失手性信息的情况下，将这些烯基硅烷转化为α，β-不饱和酮或相应的硼酸酯。[反应：看文字]
• Enzyme-Inspired Chiral Secondary-Phosphine-Oxide Ligand with Dual Noncovalent Interactions for Asymmetric Hydrogenation
  作者：Caiyou Chen、Zhefan Zhang、Shicheng Jin、Xiangru Fan、Mingyu Geng、Yan Zhou、Songwei Wen、Xinrui Wang、Lung Wa Chung、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1002/anie.201701394

  日期：2017.6.6

  Inspired by the unique character of enzymes, we developed novel chiral SPO (secondary‐phosphine‐oxide) ligand (SPO‐Wudaphos) which can enter into both ion pair and H‐bond noncovalent interactions. The novel chiral SPO‐Wudaphos exhibited excellent results in the asymmetric hydrogenation of α‐methylene‐γ‐keto carboxylic acids, affording the chiral γ‐keto acids with up to over 99 % ee. A series of control

  受酶的独特特性的启发，我们开发了新型手性SPO（仲氧化膦）配体（SPO-Wudaphos），它可以参与离子对和氢键非共价相互作用。新型手性SPO-Wudaphos在α-亚甲基-γ-酮基羧酸的不对称加氢中显示出优异的结果，使手性γ-酮酸的ee高达99％以上 。进行了一系列的控制实验和DFT计算，以说明离子对和氢键非共价相互作用的关键作用。