(E)-(R)-3-Hydroxy-2,2-dimethyl-9-oxo-dec-7-enoic acid benzyl ester | 404890-57-9

• 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)-(R)-3-Hydroxy-2,2-dimethyl-9-oxo-dec-7-enoic acid benzyl ester
• CAS: 404890-57-9
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: KBTHJTXCQYZKLV-DKISHCGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-(R)-3-Hydroxy-2,2-dimethyl-9-oxo-dec-7-enoic acid benzyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以90%的产率得到2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u
• 作为产物：
  描述：

  (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester 在 Grubbs catalyst first generation 、 nickel dichloride 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 (E)-(R)-3-Hydroxy-2,2-dimethyl-9-oxo-dec-7-enoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u