(3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methyl-2-(trimethylsilanyloxy)hexa-1,5-diene | 869631-51-6

• 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-methyl-2-(trimethylsilanyloxy)hexa-1,5-diene
• 英文别名: tert-butyl-dimethyl-[(4S)-4-methyl-2-methylidene-5-trimethylsilyloxyhex-5-enoxy]silane
• CAS: 869631-51-6
• 化学式: C₁₇H₃₆O₂Si₂
• 分子量: 328.643
• InChiKey: BTBYETMERPUFGK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  18.5
• 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-methyl-2-(trimethylsilanyloxy)hexa-1,5-diene 在 氢氟酸 、 溴化锡 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 C₃₉H₅₆O₆Si
  参考文献：
  名称：

  Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template

  摘要：

  [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.

  DOI：

  10.1021/ol0520018
• 作为产物：
  描述：

  三甲基氯硅烷 、 (3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-5-en-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以100%的产率得到(3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methyl-2-(trimethylsilanyloxy)hexa-1,5-diene
  参考文献：
  名称：

  Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template

  摘要：

  [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.

  DOI：

  10.1021/ol0520018

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.