L-苯丙氨酸,N-[(1-甲基乙氧基)羰基]-,甲基酯 | 124947-31-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: L-苯丙氨酸,N-[(1-甲基乙氧基)羰基]-,甲基酯
• 英文名称: N-(isopropoxycarbonyl)-L-phenylalanine methyl ester
• 英文别名: methyl (S)-N-(iso-propoxycarbonyl)-phenylalaninate；methyl (S)-N-(isopropoxycarbonyl)phenylalaninate；methyl (S)-N-(isopropoxycarbonyl)-phenylalaninate；methyl (2S)-3-phenyl-2-(propan-2-yloxycarbonylamino)propanoate
• CAS: 124947-31-5
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: YUWDBOLCDYSGAV-LBPRGKRZSA-N

物化性质

• 沸点：
  396.5±35.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸,N-[(1-甲基乙氧基)羰基]-,甲基酯 在 叔丁基锂 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 生成 4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n
• 作为产物：
  描述：

  氯甲酸异丙酯 在 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以70%的产率得到L-苯丙氨酸,N-[(1-甲基乙氧基)羰基]-,甲基酯
  参考文献：
  名称：

  WO2006/96994

  摘要：

  公开号：

文献信息

• A Practical Synthesis of<i>threo</i>-3-Amino-2-hydroxycarboxylic Acids
  作者：Fuyuhiko Matsuda、Teruyo Matsumoto、Masako Ohsaki、Yoshio Ito、Shiro Terashima

  DOI：10.1246/bcsj.65.360

  日期：1992.2

  An expeditious synthesis of (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid (2) and (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (4), the key components of the renin inhibitor (1) and bestatin (3), respectively, have been accomplished by featuring highly diastereoselective formation of cyanohydrin acetates from α-alkoxycarbonylamino aldehydes under phase-transfer conditions.

  已经通过在相转移条件下，以α-碳氧基氨基醛为起始物，进行高度非对映选择性的氰醇酸乙酯的形成，迅速合成了（2R,3S）-3-氨基-4-环己基-2-羟基丁酸（2）和（2S,3R）-3-氨基-2-羟基-4-苯基丁酸（4），这两者分别是肾素抑制剂（1）和贝斯坦（3）的关键成分。
• A Highly Stereoselective Synthesis of (3S,4S)-Statine and (3S,4S)-Cyclohexylstatine.
  作者：Yoshiji TAKEMOTO、Teruyo MATSUMOTO、Yoshio ITO、Shiro TERASHIMA

  DOI：10.1248/cpb.39.2425

  日期：——

  The title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (S)-leucine and (S)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of O-methyl-O-trimethylsilyl ketene acetal with an (S)-α-amino aldehyde in the presence of titanium(IV) chloride as a key step. Maximum diastereoselectivity of the aldol reaction was found to be more than 95 : 5.

  所述化合物是肾素抑制剂的合成中间体，可以通过在钛(IV)氯化物存在下，利用O-甲基-O-三甲基硅基酮烯醇与(S)-α-氨基醛进行高度立体选择性的醇反应，从(S)-亮氨酸和(S)-苯丙氨酸分别制备而成。醇反应的最大对映选择性达到了95 : 5以上。
• Fluorous Oxazolidinone Chiral Auxiliary Compounds and Methods of Manufacture
  申请人：Hultin Philip Gregory

  公开号：US20090018343A1

  公开（公告）日：2009-01-15

  The present invention relates generally to perfluoroalkyl chiral auxiliary compounds and methods of manufacture. These compounds have the functionality to effectively support the synthesis of chiral compounds in single reactions, high-throughput parallel reactions, or combinatorial reactions The invention relates to two oxazolidinone chiral auxiliaries (1) and (2): wherein R f is a perfluoroalkyl group having the general formula (CH 2 ) x —C y F 2y+1 where x=1-5 and y=4-10 and wherein B is an unfunctionalized aryl, alkyl or arylalkyl group in a preferred embodiment, x=2 and y=6 and B is derived from unfunctionalized amino acids The amino acids may be from either the D- or L-series, and are preferably enantiomerically pure or in very high enantiomeric excess in either configuration.

  本发明涉及全氟烷基手性辅助化合物及其制造方法。这些化合物具有有效支持手性化合物在单反应、高通量并行反应或组合反应中合成的功能。本发明涉及两种噁唑烷手性辅助剂（1）和（2）：其中Rf是具有一般式（CH2）x - CyF2y + 1的全氟烷基，其中x = 1-5，y = 4-10，B是非功能化芳基，烷基或芳基烷基组，在优选实施例中，x = 2，y = 6，B来源于非功能化氨基酸。氨基酸可以来自D-或L系列，并且最好在任何构型中具有对映纯或非常高的对映选择性。
• An expeditious synthesis of (3S,4S)-statine and (3S,4S)cyclohexylstatine
  作者：Yoshiji Takemoto、Teruyo Matsumoto、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)94374-0

  日期：1990.1
• Harada, Hiromu; Iyobe, Akira; Tsubaki, Atsushi, Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2497 - 2500
  作者：Harada, Hiromu、Iyobe, Akira、Tsubaki, Atsushi、Yamaguchi, Toshiaki、Hirata, Kazuma、et al.

  DOI：——

  日期：——