(2S,3R)-methyl 2-methyl-3-hydroxy-(E)-4-hexenoate | 98244-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3R)-methyl 2-methyl-3-hydroxy-(E)-4-hexenoate
• 英文别名: methyl (E,2S,3R)-3-hydroxy-2-methylhex-4-enoate
• CAS: 98244-11-2
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: JEHGEKPSUMDBCP-LYNIJRAASA-N

物化性质

• 沸点：
  228.9±20.0 °C(predicted)
• 密度：
  1.014±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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

• 作为产物：
  描述：

  (E,2S,3R)-3-hydroxy-1-[(3S,4S)-5-[(E,2S,3R)-3-hydroxy-2-methylhex-4-enoyl]-1,1-dioxo-3,4-diphenyl-1,2,5-thiadiazolidin-2-yl]-2-methylhex-4-en-1-one 在 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-methyl 2-methyl-3-hydroxy-(E)-4-hexenoate
  参考文献：
  名称：

  Asymmetric aldol reactions employing a cyclic sulfamide chiral auxiliary

  摘要：

  DOI：

  10.1016/s0040-4039(00)61012-2

文献信息

• Bornane sultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldols
  作者：Wolfgang Oppolzer、Julian Blagg、Ines Rodriguez、Eric Walther

  DOI：10.1021/ja00163a045

  日期：1990.3

  La configuration absolue est controlee par le choix du centre ion (M=B, Li ou Sn(IV)) de l'enolate des N-acylsultames

  La configuration absolue est controlee par le choix du center ion (M=B, Li ou Sn(IV)) de l'enolate des N-acylsultames
• Asymmetric aldol reactions: a novel model for switching between chelation- and non-chelation-controlled aldol reactions
  作者：Tu Hsin Yan、Chang Wei Tan、Hui Chun Lee、Hua Chi Lo、Tzung Yu Huang

  DOI：10.1021/ja00060a010

  日期：1993.4

  A new camphor-based N-propionyloxazolidinethione provides remarkable levels of asymmetric induction for both chelation-and non-chelation-controlled aldol processes. While the aldol condensation of the derived di-n-butylboryl enolate with various aldehydes affords the 'Evans'' syn aldol with excellent diastereoselectivity, the chlorotitanium enolate gives the ''non-Evans' syn aldol expected from chelation control. Most noteworthy is the observation that the sense of facial selectivity from the chlorotitanium enolate of propionyloxazolidinethione is opposite to that obtained from propionyloxazolidinone. This important finding illustrates the importance of increased chelating potential of the enolate ligand, ring thiocarbonyl, in maximizing the aldol pi-facial discrimination. Final nondestructive chiral auxiliary removal via hydroperoxide-assisted hydrolysis and subsequent esterification provides enantiomerically pure methoxy-carbonyl aldols.
• Generation of (<i>E</i>)-Silylketene Acetals in a Rhodium-DuPhos Catalyzed Two-Step Reductive Aldol Reaction
  作者：Cun-Xiang Zhao、Jonathan Bass、James P. Morken

  DOI：10.1021/ol016279l

  日期：2001.9.1

  [GRAPHICS]Mechanistic studies employing in situ NMR analysis implicate intermediate silicon enolates as reactive intermediates in the Rh-DuPhos catalyzed two-step reductive aldol reaction with Cl2MeSiH. These enolates undergo noncatalyzed reaction with a variety of aldehydes to give the derived syn-aldol adduct in high yields and diastereoselection.
• Enantioselective synthesis of anti-.alpha.-methyl-.beta.-hydroxy esters through titanium tetrachloride-mediated aldol condensation
  作者：Cesare Gennari、Anna Bernardi、Lino Colombo、Carlo Scolastico

  DOI：10.1021/ja00306a045

  日期：1985.10
• OPPOLZER, WOLFGANG;BLAGG, JULIAN;RODRIGUEZ, INES;WALTHER, ERIC, J. AMER. CHEM. SOC., 112,(1990) N, C. 2767-2772
  作者：OPPOLZER, WOLFGANG、BLAGG, JULIAN、RODRIGUEZ, INES、WALTHER, ERIC

  DOI：——

  日期：——