(2R,5R)-1-tert-butoxycarbonyl-2,5-diphenylpiperazine | 148624-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2R,5R)-1-tert-butoxycarbonyl-2,5-diphenylpiperazine
• 英文别名: tert-butyl (2R,5R)-2,5-diphenylpiperazine-1-carboxylate
• CAS: 148624-13-9
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: PSRRPQZKNLSODL-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-tert-butoxycarbonyl-2,5-diphenylpiperazine 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 1,1'-ethylenebis<(2R,5R)-2,5-diphenylpiperazine>
  参考文献：
  名称：

  Chiral Piperazines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes.

  摘要：

  研究了在催化量的手性哌嗪衍生物存在下苯甲醛与二乙基锌的对映选择性乙基化。手性哌嗪在烷基化反应中作为不对称催化剂，产生具有中等对映选择性的 1-苯基丙醇。讨论了哌嗪环的结构变化对不对称诱导的影响及其机制。

  DOI：

  10.1248/cpb.41.1557
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2R,5R)-2,5-bis(phenyl)piperazine 以 二氯甲烷 为溶剂， 反应 1.0h， 以53%的产率得到(2R,5R)-1-tert-butoxycarbonyl-2,5-diphenylpiperazine
  参考文献：
  名称：

  Hydrochloride of chiral piperazine as a chiral proton source

  摘要：

  Asymmetric protonation utilizing hydrochlorides of chiral piperazine derivatives has been investigated. Protonation of the lithium enolate derived from 1-acetoxy-2-benzylcyclohexene with (2R, 5R)-2,5-diphenylpiperazine monohydrochloride (2) resulted in a formation of (S)-2-benzylcyclohexanone in 70% ee. The enantioface-differrentiating protonation with the salts of related chiral piperazine derivatives are also discussed.

  DOI：

  10.1016/s0957-4166(00)82345-9

文献信息

• Polyaza macrocycles containing the piperazine ring as a semi-flexible moiety
  作者：Kaoru Fuji、Kiyosei Takasu、Hisashi Miyamoto、Kiyoshi Tanaka、Tooru Taga

  DOI：10.1016/0040-4039(96)01586-9

  日期：1996.9

  Azamacrocycles 1–4 were synthesized from 9 in 20–30% overall yields. Compounds 1 and 2 extracted some metal ions into organic solvents, but 3 and 4 did not. The crystal structure of the Ag(I) complex of 1 has been determined.

  Azamacrocycles 1-4由9合成，总产率为20-30％。化合物1和2将一些金属离子提取到有机溶剂中，而化合物3和4则没有。Ag（I）配合物1的晶体结构已经确定。
• Asymmetric cis-dihydroxylation of olefins by utilizing chiral bispiperazine
  作者：Kaoru Fuji、Kiyoshi Tanaka、Hisashi Miyamoto

  DOI：10.1016/0040-4039(92)88090-r

  日期：1992.7

  Asymmetric dihydroxylation of a variety of olefins has been achieved by employing the chiral ligands of N,N'-dialkyl bispiperazines having linker arm of two carbons in excellent to good enantioselectivity.
• Facile synthesis of optically active cis-2,5-diphenyl-1,4-diazabicyclo[2.2.2]octane
  作者：Kaoru Fuji、Kiyoshi Tanaka、Kiyosei Takasu、Tooru Taga

  DOI：10.1016/0957-4166(96)00209-1

  日期：1996.6

  Enantiomerically pure (1R,2R,4R,5R)- and (1S,2R,4S,5R)-2,5-diphenyl-1,4-diazabicyclo[2.2.2]octane (2,5-diphenyl-DABCO) have been prepared and their crystal structures studied. Copyright (C) 1996 Elsevier Science Ltd
• Hydrochloride of chiral piperazine as a chiral proton source
  作者：Kaoru Fuji、Kiyoshi Tanaka、Hisashi Miyamoto

  DOI：10.1016/s0957-4166(00)82345-9

  日期：1993.2

  Asymmetric protonation utilizing hydrochlorides of chiral piperazine derivatives has been investigated. Protonation of the lithium enolate derived from 1-acetoxy-2-benzylcyclohexene with (2R, 5R)-2,5-diphenylpiperazine monohydrochloride (2) resulted in a formation of (S)-2-benzylcyclohexanone in 70% ee. The enantioface-differrentiating protonation with the salts of related chiral piperazine derivatives are also discussed.
• Chiral Piperazines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes.
  作者：Kaoru FUJI、Kiyoshi TANAKA、Hisashi MIYAMOTO

  DOI：10.1248/cpb.41.1557

  日期：——

  Enantioselective ethylation of benzaldehyde with diethylzinc in the presence of a catalytic amount of chiral piperazine derivatives was investigated. The chiral piperazine works as an asymmetric catalyst in the alkylation, yielding 1-phenylpropanol with a moderate enantioselectivity. The influence of structural variation of the piperazine ring upon the asymmetric induction and the mechanism involved are discussed.

  研究了在催化量的手性哌嗪衍生物存在下苯甲醛与二乙基锌的对映选择性乙基化。手性哌嗪在烷基化反应中作为不对称催化剂，产生具有中等对映选择性的 1-苯基丙醇。讨论了哌嗪环的结构变化对不对称诱导的影响及其机制。