(E)-ethyl 3-((4R,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate | 914366-84-0

• 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)-ethyl 3-((4R,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate
• CAS: 914366-84-0
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: CCCMYNJKRJVAEB-JVVNSHGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-((4R,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以98%的产率得到(E,4R,5R)-ethyl 5-hydroxy-4-methylhex-2-enoate
  参考文献：
  名称：

  De Novo Synthesis of 2-Substituted syn-1,3-Diols via an Iterative Asymmetric Hydration Strategy

  摘要：

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

  DOI：

  10.1021/jo061200h
• 作为产物：
  描述：

  ethyl (2E,4E)-4-methylhexa-2,4-dienoate 在 甲基磺酰胺 、 potassium carbonate 吡啶 、 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 0.08h， 生成 (E)-ethyl 3-((4R,5R)-4,5-dimethyl-2-oxo-1,3-dioxolan-4-yl)acrylate
  参考文献：
  名称：

  De Novo Synthesis of 2-Substituted syn-1,3-Diols via an Iterative Asymmetric Hydration Strategy

  摘要：

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

  DOI：

  10.1021/jo061200h

文献信息

• Asymmetric - Hydroxylation via Epoxidation-Carboxylation: A Formal Synthesis of (+)-Citreoviral
  作者：Barry M Trost、John K Lynch、Steven R Angle

  DOI：10.1016/s0040-4039(00)95732-0

  日期：1987.1

  Asymmetric epoxidation of tiglyl alcohol combined with Pd(0) catalyzed conversion to the vicinal diol with retention of configuration provides an efficient asymmetric synthesis of a key intermediate to (+)-citreoviral and related compounds.

  tiglyl醇的不对称环氧化与Pd（0）催化的邻位二醇的转化并保留构型，为（+）-柠檬病毒和相关化合物的关键中间体提供了有效的不对称合成。