(S)-3-phenylbutyric acid tert-butyl ester | 67217-41-8

• 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)-3-phenylbutyric acid tert-butyl ester
• 英文别名: (S)-tert-butyl 3-phenylbutanoate；tert-butyl (S)-3-phenylbutanoate；tert-butyl (S)-phenylbutanoate；(S)-t-butyl 3-phenylbutanoate；tert-butyl (3S)-3-phenylbutanoate
• CAS: 67217-41-8
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: WBQGPKOCUYDNGK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-phenylbutyric acid tert-butyl ester 在 六甲基磷酰三胺 、 氯化亚砜 、 sodium azide 、 四丁基溴化铵 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  New Chiral Ligands with Nonstereogenic Chirotopic Centers for Asymmetric Synthesis

  摘要：

  Pseudo-C2 -symmetrical ligands have been prepared efficiently: The attachment of the chiral alkyl group to the heteroatom (P or N) through a nonstereogenic, chirotopic carbon center facilitates their synthesis as the configuration at this carbon atom no longer needs to be controlled. Two such ligands were combined, for example, in the base 1, which is especially useful for asymmetric deprotonation of prochiral ketones [Eq. (a)].

  DOI：

  10.1002/(sici)1521-3773(19981116)37:21<3014::aid-anie3014>3.0.co;2-6
• 作为产物：
  描述：

  tert-butyl (E)-3-phenylbut-2-enoate 在 乙二醇二甲醚溴化镍 、 indium 、 水 、 四丁基碘化铵 、 溶剂黄146 、 (-)-1,2-双[(2R,5R)-2,5-二甲基磷]苯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到(S)-3-phenylbutyric acid tert-butyl ester
  参考文献：
  名称：

  镍催化烯烃的不对称Umpolung加氢和氘代。

  摘要：

  使用乙酸或水作为氢源，铟粉作为电子给体，镍催化几种烯烃的不对称氢化反应以高对映选择性进行。本文中烯烃的范围包括α，β-不饱和酯，腈和酮以及烯丙醇。α，β-不饱和酯的不对称氘化也可以通过氘水（最便宜的氘源）实现。

  DOI：

  10.1021/acs.orglett.0c00112

文献信息

• Highly Enantioselective Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions of Arylboronic Acids to Acyclic α,β-Unsaturated Compounds: The Formal Synthesis of (−)-Indatraline
  作者：Wei-Ting Wei、Jiann-Yih Yeh、Ting-Shen Kuo、Hsyueh-Liang Wu

  DOI：10.1002/chem.201102073

  日期：2011.10.4

  were synthesized from (−)‐5‐oxobornyl acetate and utilized in the asymmetric 1,4‐addition reaction of arylboronic acids with acyclic α,β‐unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (−)‐indatraline.

  是做二烯就是做的：稳定的手性双环[2.2.1]二烯配体是由（-）-5-氧代冰片乙酸酯合成的，用于芳基硼酸与无环α，β-不饱和化合物的不对称1,4加成反应。由1和[RhCl（C 2 H 4）2 } 2 ]原位生成的络合物的低催化负载量提供了良好至优异收率和优异对映选择性的加合物。该方法用于（-）-茚达林的正式全合成。
• Asymmetric Conjugate Reduction of α,β-Unsaturated Esters with Chiral Rhodium(bisoxazolinylphenyl) Catalysts
  作者：Hisao Nishiyama、Yasunori Tsuchiya、Yoshinori Kanazawa、Takushi Shiomi、Kazuki Kobayashi

  DOI：10.1055/s-2004-834791

  日期：——

  Chiral rhodium(bisoxazolinylphenyl) complexes reduced α,β-unsaturated esters in high enantioselectivity up to 97-98% ee in the combination of alkoxyhydrosilanes.

  手性铑（双恶唑啉基苯基）配合物在烷氧基氢硅烷的组合中以高对映选择性还原 α,β-不饱和酯，ee 高达 97-98%。
• Nickel-catalyzed asymmetric transfer hydrogenation of conjugated olefins
  作者：Siyu Guo、Peng Yang、Jianrong (Steve) Zhou

  DOI：10.1039/c5cc01632k

  日期：——

  Asymmetric transfer hydrogenation of electron-deficient olefins is realized with nickel catalysts supported by strongly [sigma]-donating bisphosphines. Deuterium labeling experiments points to a reaction sequence of formate decarboxylation, asymmetric hydride insertion...

  缺电子的烯烃的不对称转移氢化是由强σ供体双膦负载的镍催化剂实现的。氘标记实验指出甲酸脱羧，不对称氢化物插入的反应顺序...
• Chiral ferrocenyl phosphine-phosphoramidite ligands for Cu-catalyzed asymmetric conjugate reduction of α,β-unsaturated esters
  作者：Chuan-Jin Hou、Wei-Lei Guo、Xiang-Ping Hu、Jun Deng、Zhuo Zheng

  DOI：10.1016/j.tetasy.2011.01.022

  日期：2011.1

  Unsymmetrical hybrid chiral ferrocenyl phosphine-phosphoramidite ligands have been applied for the first time in the Cu-catalyzed asymmetric 1,4-reduction of β-aryl substituted α,β-unsaturated esters. The results show that the ligand bearing (Sc)-central, (Rp)-planar, and (Ra)-axial chiralities gave the best performance. The present catalytic system proved to be highly substrate-dependent, catalyzing

  不对称杂化手性二茂铁基二茂铁膦-亚磷酰胺配体已首次应用在Cu催化的β-芳基取代的α，β-不饱和酯的1，对称的1,4-还原中。结果表明，具有（S c）-中心，（R p）-平面和（R a）-轴向手性的配体具有最佳性能。本催化体系证明是高度依赖底物的，以中等至极好的对映选择性催化α，β-不饱和酯的共轭还原。
• New Homochiral Ligands Bearing Nonstereogenic Chirotopic Centers. Lithiated <i>N</i>,<i>N</i><i>‘</i>-Dialkylureas as Chiral Bases and Sterically Crowded Phosphines for Asymmetric Catalysis
  作者：Claus-Dieter Graf、Christophe Malan、Klaus Harms、Paul Knochel

  DOI：10.1021/jo990412u

  日期：1999.7.1

  The synthesis of new homochiral pseudo-C-2-symmetrical ligands of type 1 bearing a nonstereogenic chirotopic center is reported. Two such structural units are combined in the ureas 2 and 10, which proved to be useful for enantioselective deprotonation and alkylation of ketones (up to 88% ee). The monophosphine 3 induced a high enantiomeric excess in the Pd-catalyzed allylation of dimethyl malonate (up to 73% ee). Furthermore, we have shown that the achiral sterically crowded alkyl diphosphine 23 efficiently stabilized Pd(0) at high temperatures.