(S)-5-Hydroxymethyl-3-methyl-hex-5-en-2-one | 791131-38-9

• 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: (S)-5-Hydroxymethyl-3-methyl-hex-5-en-2-one
• 英文别名: (3S)-5-(hydroxymethyl)-3-methylhex-5-en-2-one
• CAS: 791131-38-9
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: COCOLDKUUJMKAN-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-Hydroxymethyl-3-methyl-hex-5-en-2-one 在 4-二甲氨基吡啶 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2,5-dioxo-hexyl ester
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x
• 作为产物：
  描述：

  (3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-5-en-2-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以65%的产率得到(S)-5-Hydroxymethyl-3-methyl-hex-5-en-2-one
  参考文献：
  名称：

  Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C

  摘要：

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

  DOI：

  10.1021/ol048396x

文献信息

• Syntheses of the C(1−6) and C(19−24) Fragments of Lituarines A, B, and C
  作者：Jeremy Robertson、Jonathan W. P. Dallimore、Paul Meo

  DOI：10.1021/ol048396x

  日期：2004.10.1

  Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.