(3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-5-en-2-one | 791131-37-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-5-en-2-one
• 英文别名: (3S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methylhex-5-en-2-one
• CAS: 791131-37-8
• 化学式: C₁₄H₂₈O₂Si
• 分子量: 256.461
• InChiKey: DIGITFQAADMMMJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol 在 咪唑 、 碘 、 三苯基膦 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 (3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-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

• Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template
  作者：Jeremy Robertson、Jonathan W. P. Dallimore

  DOI：10.1021/ol0520018

  日期：2005.10.1

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.