E-(S)-ethyl 4-hydroxy-3-methyl-pent-2-enoate | 167936-74-5

• 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: E-(S)-ethyl 4-hydroxy-3-methyl-pent-2-enoate
• 英文别名: Ethyl (4S,E)-4-hydroxy-3-methylpent-2-enoate；ethyl 4-hydroxy-3-methylpent-2-enoate；ethyl (E,4S)-4-hydroxy-3-methylpent-2-enoate
• CAS: 167936-74-5
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HYDMODAHOUGOTB-XPPMVYLVSA-N

物化性质

• 沸点：
  242.0±23.0 °C(predicted)
• 密度：
  1.018±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  E-(S)-ethyl 4-hydroxy-3-methyl-pent-2-enoate 在 臭氧 、 sodium sulfite 作用下， 生成 (S)-acetoin
  参考文献：
  名称：

  Koul, Surinder; Crout, David H. G.; Errington, William, Journal of the Chemical Society. Perkin transactions I, 1995, # 23, p. 2969 - 2988

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (E,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylpent-2-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到E-(S)-ethyl 4-hydroxy-3-methyl-pent-2-enoate
  参考文献：
  名称：

  Aldol-Type Chirons from Asymmetric Hydrogenations of Trisubstituted Alkenes

  摘要：

  Catalyst control dominates in the asymmetric hydrogenations of largely unfunctionalized trisubstituted alkenes formed from lactic acid and glyceraldehyde, affording syn- and ant aldol products of the type shown above.

  DOI：

  10.1021/ol900308w

文献信息

• Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids and of α,β-Unsaturated γ-Amino Acids. SN2- vs. SN2’-Dichotomy of the Mitsunobu Amination of Allylic Alcohols
  作者：Johann Mulzer、Günther Funk

  DOI：10.1055/s-1995-3847

  日期：1995.1

  Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean SN2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities.

  本文描述了从（R）-异丙叉甘油醛和乙基（S）-乳酸分别合成光学纯的β,γ-不饱和α-氨基酸和α,β-不饱和γ-氨基酸的新颖且高效的方法（总步骤为6-9步，总收率为10-30%）。关键步骤是手性仲烯丙醇与酞酰亚胺作为亲核试剂的 Mitsunobu 反应，首次观察到α,γ 烯丙基重排现象。研究了结构-α,γ 比例关系以及烯丙基重排的立体化学。α-取代过程通过干净的 SN2 反转进行，而γ-取代对应于亲核试剂的（E）-反向攻击，具有不同的立体选择性。
• Determination of the absolute configuration of the diterpene tonantzitlolone B
  作者：Torsten Busch、Hannah Schuster、Andreas Kirschning

  DOI：10.1016/j.tetlet.2008.06.105

  日期：2008.9

  work synthetic and semi-synthetic studies toward the antitumor active natural product tonantzitlolone B are described, starting with an advanced intermediate obtained from the total synthesis of tonantzitlolone and a natural sample of this compound, respectively. The unknown absolute configuration of the stereogenic center in the side chain was elucidated to be (R).

  在这项工作中，描述了对抗肿瘤活性天然产物tontzitlolone B的合成和半合成研究，分别从从tonttzitlolone和该化合物的天然样品的总合成中获得的高级中间体开始。侧链中立体异构中心的未知的绝对构型被阐明为（R）。
• Highly Stereoselective Epoxidation of α-Methyl-γ-hydroxy-α,β-unsaturated Esters:  Rationalization and Synthetic Applications
  作者：Irakusne López、Santiago Rodríguez、Javier Izquierdo、Florenci V. González

  DOI：10.1021/jo0709955

  日期：2007.8.1

  The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha, beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.
• Aldol-Type Chirons from Asymmetric Hydrogenations of Trisubstituted Alkenes
  作者：Jian Zhao、Kevin Burgess

  DOI：10.1021/ol900308w

  日期：2009.5.21

  Catalyst control dominates in the asymmetric hydrogenations of largely unfunctionalized trisubstituted alkenes formed from lactic acid and glyceraldehyde, affording syn- and ant aldol products of the type shown above.
• Koul, Surinder; Crout, David H. G.; Errington, William, Journal of the Chemical Society. Perkin transactions I, 1995, # 23, p. 2969 - 2988
  作者：Koul, Surinder、Crout, David H. G.、Errington, William、Tax, Jiri

  DOI：——

  日期：——