(3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]hexanedial | 349449-41-8

• 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,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]hexanedial
• CAS: 349449-41-8
• 化学式: C₁₈H₃₈O₄Si₂
• 分子量: 374.668
• InChiKey: PNLZAEWOCHDTMR-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]hexanedial 在 Cp2Ti(Ph)Cl 三甲基氯硅烷 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以55%的产率得到(1S,2S,4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexane-1,2-diol
  参考文献：
  名称：

  Diastereoselective Inter- and Intramolecular Pinacol Coupling of Aldehydes Promoted by Monomeric Titanocene(III) Complex Cp₂TiPh

  摘要：

  A monomeric titanocene(III) derivative, Cp2TiPh, effectively promoted the pinacol coupling of both an aromatic aldehyde, benzaldehyde, and an aliphatic aldehyde, 3-phenylpropionaldehyde. The same reactive complex was successfully generated by a catalytic amount of a precursor, Cp2Ti-(PH)Cl and its stoichiometric amount of Zn. The Cp2TiPh-catalyzed pinacol coupling of benzaldehyde derivatives and aliphatic aldehydes afforded the corresponding 1,2-diols in high yields with moderate to good three-selectivity. On the other hand, Cp2TiPh-catalyzed pinacol cyclization of dials gave cyclic 1,2-diols with excellent diastereoselectivity. The extension of this protocol to chiral dials demonstrated that the phenyltitanium complex catalytically transmitted an axial chirality or a central chirality of the starting dials to the central chirality of the resultant l,a-diols.

  DOI：

  10.1021/jo001781p
• 作为产物：
  描述：

  (4S,5S)-4,5-dihydroxyocta-1,7-diene 在 4-二甲氨基吡啶 、 氧气 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.67h， 生成 (3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]hexanedial
  参考文献：
  名称：

  Diastereoselective Inter- and Intramolecular Pinacol Coupling of Aldehydes Promoted by Monomeric Titanocene(III) Complex Cp₂TiPh

  摘要：

  A monomeric titanocene(III) derivative, Cp2TiPh, effectively promoted the pinacol coupling of both an aromatic aldehyde, benzaldehyde, and an aliphatic aldehyde, 3-phenylpropionaldehyde. The same reactive complex was successfully generated by a catalytic amount of a precursor, Cp2Ti-(PH)Cl and its stoichiometric amount of Zn. The Cp2TiPh-catalyzed pinacol coupling of benzaldehyde derivatives and aliphatic aldehydes afforded the corresponding 1,2-diols in high yields with moderate to good three-selectivity. On the other hand, Cp2TiPh-catalyzed pinacol cyclization of dials gave cyclic 1,2-diols with excellent diastereoselectivity. The extension of this protocol to chiral dials demonstrated that the phenyltitanium complex catalytically transmitted an axial chirality or a central chirality of the starting dials to the central chirality of the resultant l,a-diols.

  DOI：

  10.1021/jo001781p

文献信息

• Diastereoselective Inter- and Intramolecular Pinacol Coupling of Aldehydes Promoted by Monomeric Titanocene(III) Complex Cp₂TiPh
  作者：Yoshihiko Yamamoto、Reiko Hattori、Takeyuki Miwa、Yu-ichiro Nakagai、Takateru Kubota、Chiyo Yamamoto、Yoshio Okamoto、Kenji Itoh

  DOI：10.1021/jo001781p

  日期：2001.6.1

  A monomeric titanocene(III) derivative, Cp2TiPh, effectively promoted the pinacol coupling of both an aromatic aldehyde, benzaldehyde, and an aliphatic aldehyde, 3-phenylpropionaldehyde. The same reactive complex was successfully generated by a catalytic amount of a precursor, Cp2Ti-(PH)Cl and its stoichiometric amount of Zn. The Cp2TiPh-catalyzed pinacol coupling of benzaldehyde derivatives and aliphatic aldehydes afforded the corresponding 1,2-diols in high yields with moderate to good three-selectivity. On the other hand, Cp2TiPh-catalyzed pinacol cyclization of dials gave cyclic 1,2-diols with excellent diastereoselectivity. The extension of this protocol to chiral dials demonstrated that the phenyltitanium complex catalytically transmitted an axial chirality or a central chirality of the starting dials to the central chirality of the resultant l,a-diols.