(E)-(2S)-1,2-isopropylidene-3-hepten-5-one | 117729-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(2S)-1,2-isopropylidene-3-hepten-5-one
• 英文别名: (E)-1,2,4,5-tetradeoxy-6,7-O-isopropylidene-D-glycero-hept-4-en-3-ulose；(E)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]pent-1-en-3-one
• CAS: 117729-02-9
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: DTVYLYCFYXYFCT-CYNONHLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(2S)-1,2-isopropylidene-3-hepten-5-one 生成 1,2-dideoxy-6,7-O-isopropylidene-D-arabino-9-heptulose
  参考文献：
  名称：

  CUBERO, ISIDORO IZQUIERDO;LOPEZ-ESPINOSA, MARIA T. PLAZA, CARBOHYDR. RES., 173,(1988) N 1, 41-52

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(三苯基膦)-2-丁酮 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 以 二氯甲烷 为溶剂， 反应 48.0h， 以42%的产率得到(E)-(2S)-1,2-isopropylidene-3-hepten-5-one
  参考文献：
  名称：

  Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

  摘要：

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.

  DOI：

  10.1021/jo0488311

文献信息

• Synthesis of 1,2-dideoxy-3-heptulose derivatives
  作者：Isidoro Izquierdo Cubero、Maria T. Plaza López-Espinosa

  DOI：10.1016/s0008-6215(00)90801-2

  日期：1988.2

  -isopropylidene-β- d - arabino -3-heptulo-3,7-pyranose, 1,2-dideoxy-4,5:6,7-di- O -isopropylidene- keto - d - arabino -3-heptulose, and 1,2-dideoxy-3,4:5, 7-di- O -isopropylidene-α- d - xylo -3-heptulo-3,6-furanose. Deacetonation of 5, 7, 9 , and 11 gave 1,2-dideoxy- d - lyxo -, - d - ribo , - d - arabino -, and - d - xylo -3-heptulose, respectively.

  摘要2,3-O-异亚丙基-d-甘油醛与三苯基（丙酰基-亚甲基）膦烷反应生成（Z）-（3）和（E）-1,2,4,5-四脱氧-6，通过色谱法分离的7-O-异亚丙基-d-甘油-庚-4-en-3-ulose（4）。用四氧化将3羟基化，得到1,2-二脱氧-6,7-O-异亚丙基-d-lyxo-（5）和-d-核糖-3-庚糖（7），将其通过柱色谱法分离。类似地，4给出了可以通过色谱法部分拆分的1,2-二脱氧-6,7-O-异亚丙基-d-阿拉伯糖-（9）和-d-木基-3-庚糖（11）的混合物。丙酮化时，5和7得到1,2-二脱氧-4,5-O-异亚丙基-d-lyxo-3-庚七-3,6-呋喃糖和3,7-脱水-1,2-二脱氧-4,5 -O-异亚丙基-β-d-核糖-3-庚-7,6-呋喃糖 而9和11的混合物给出了1,2-二脱氧-3,4：5,6-二-O-异亚丙基-β-d-阿拉伯-3-庚七-3,7-吡喃糖，1,2-二脱氧-
• CUBERO, ISIDORO IZQUIERDO;LOPEZ-ESPINOSA, MARIA T. PLAZA, CARBOHYDR. RES., 173,(1988) N 1, 41-52
  作者：CUBERO, ISIDORO IZQUIERDO、LOPEZ-ESPINOSA, MARIA T. PLAZA

  DOI：——

  日期：——
• Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes
  作者：Eelco Ruijter、Heike Schültingkemper、Ludger A. Wessjohann

  DOI：10.1021/jo0488311

  日期：2005.4.1

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.