(3R)-1-methoxy-3-methyl-4-phenylmethoxybutan-2-one | 149915-83-3

• 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: (3R)-1-methoxy-3-methyl-4-phenylmethoxybutan-2-one
• CAS: 149915-83-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: XWJOWGADMBDGFG-LLVKDONJSA-N

物化性质

• 沸点：
  328.6±22.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (3R)-1-methoxy-3-methyl-4-phenylmethoxybutan-2-one 在 氯代二环己基硼烷 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 (E)-(2R,3S,4S,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-2,6,8-trimethyl-non-6-ene-3,5-diol
  参考文献：
  名称：

  High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin

  摘要：

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).

  DOI：

  10.1021/jo00068a002
• 作为产物：
  描述：

  methoxymethyllithium 、 Weinreb amide 以 四氢呋喃 为溶剂， 以80%的产率得到(3R)-1-methoxy-3-methyl-4-phenylmethoxybutan-2-one
  参考文献：
  名称：

  High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin

  摘要：

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).

  DOI：

  10.1021/jo00068a002

文献信息

• High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin
  作者：Ian Paterson、Richard D. Tillyer

  DOI：10.1021/jo00068a002

  日期：1993.7

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).