(R)-3-Acryloyloxy-2,2-dimethyl-hex-5-enoic acid benzyl ester | 404890-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-Acryloyloxy-2,2-dimethyl-hex-5-enoic acid benzyl ester
• 英文别名: benzyl (3R)-2,2-dimethyl-3-prop-2-enoyloxyhex-5-enoate
• CAS: 404890-50-2
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: KGTNUXQSJQCRFN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-Acryloyloxy-2,2-dimethyl-hex-5-enoic acid benzyl ester 在 Grubbs catalyst first generation 、 nickel dichloride sodium tetrahydroborate 、 氯代二环己基硼烷 、 potassium tert-butylate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 37.17h， 生成 2-{(2R,6S)-6-[(4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-4-hydroxy-5-methyl-2-oxo-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-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：

  2-甲酰基-2-甲基丙酸苄酯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-3-Acryloyloxy-2,2-dimethyl-hex-5-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

文献信息

• Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448
  作者：Ashoke Bhattacharjee、Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol016938u

  日期：2002.2.1

  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.