(R)-7-Benzyloxy-5-hydroxy-hept-1-en-3-one | 152035-82-0

• 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)-7-Benzyloxy-5-hydroxy-hept-1-en-3-one
• 英文别名: (5R)-5-hydroxy-7-phenylmethoxyhept-1-en-3-one
• CAS: 152035-82-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: FHCGFOQLHQGHKU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-7-Benzyloxy-5-hydroxy-hept-1-en-3-one 在 sodium tetrahydroborate 、 二乙基甲氧基硼烷 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(3R,5R)-7-(benzyloxy)-1-heptene-3,5-diol
  参考文献：
  名称：

  Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction

  摘要：

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).

  DOI：

  10.1016/s0040-4039(00)74050-0
• 作为产物：
  描述：

  (R)-7-Benzyloxy-5-(tetrahydro-pyran-2-yloxy)-hept-1-en-3-ol 在 溶剂黄146 作用下， 生成 (R)-7-Benzyloxy-5-hydroxy-hept-1-en-3-one
  参考文献：
  名称：

  Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction

  摘要：

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).

  DOI：

  10.1016/s0040-4039(00)74050-0

文献信息

• Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction
  作者：Kazutsugu Matsumoto、Masayuki Shimagaki、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)74050-0

  日期：1993.7

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).