cis-N-(Carbobenzyloxy)-2,6-dimethylpiperidine | 91083-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-N-(Carbobenzyloxy)-2,6-dimethylpiperidine
• 英文别名: benzyl (2R,6S)-2,6-dimethylpiperidine-1-carboxylate
• CAS: 91083-66-8
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: OWDOUERXHFTHJS-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-N-(Carbobenzyloxy)-2,6-dimethylpiperidine 在 fungus Beauveria bassiana ATCC 7159 、 水 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以5%的产率得到(2S,4S,6R)-4-Hydroxy-2,6-dimethyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159

  摘要：

  与真菌 Beauveria bassiana ATCC 7159 培养时，受 N-苄氧羰基（Cbz）保护的哌啶会发生羟基化反应，其区域选择性要高于相应的 N-苯甲酰基类似物。Cbz 保护的哌啶 1-3、5-7 通过这种真菌的生长细胞悬浮液进行生物转化，主要产生 4-羟基化产物，收率高达 48%。羟基化的区域特异性仅在 N-苄氧羰基-3-甲基哌啶 3 和 N-苄氧羰基-2-甲基哌啶 4 中受到明显影响，羟基化发生在 3 和 4 位。

  DOI：

  10.1039/a805800h
• 作为产物：
  描述：

  benzyl hept-6-en-2-ylcarbamate 在 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基氢氧化铵 、 mercury(II) trifluoroacetate 、 三氟乙酸 作用下， 生成 cis-N-(Carbobenzyloxy)-2,6-dimethylpiperidine
  参考文献：
  名称：

  Applications of intramolecular amidomercuration. 3. Stereoselectivity in intramolecular amidomercuration. Kinetic vs. thermodynamic control

  摘要：

  DOI：

  10.1021/jo00189a048

文献信息

• Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159
  作者：Suzanne J. Aitken、Gideon Grogan、Cathy S.-Y. Chow、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1039/a805800h

  日期：——

  N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues when incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protected piperidines 1–3, 5–7, have been biotransformed by growing cell suspensions of this fungus to yield predominantly 4-hydroxylated products in up to 48% yield. The regiospecificity of hydroxylation was only compromised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-methylpiperidine 4 where hydroxylation occurred in both the 3 and 4 positions.

  与真菌 Beauveria bassiana ATCC 7159 培养时，受 N-苄氧羰基（Cbz）保护的哌啶会发生羟基化反应，其区域选择性要高于相应的 N-苯甲酰基类似物。Cbz 保护的哌啶 1-3、5-7 通过这种真菌的生长细胞悬浮液进行生物转化，主要产生 4-羟基化产物，收率高达 48%。羟基化的区域特异性仅在 N-苄氧羰基-3-甲基哌啶 3 和 N-苄氧羰基-2-甲基哌啶 4 中受到明显影响，羟基化发生在 3 和 4 位。
• Biohydroxylation Reactions Catalyzed by Enzymes and Whole-Cell Systems
  作者：Sabine L. Flitsch、Suzanne J. Aitken、Cathy S.-Y. Chow、Gideon Grogan、Adam Staines

  DOI：10.1006/bioo.1999.1135

  日期：1999.4

  The biohydroxylation of a number of cyclic substrates (3-24) containing aromatic side chains was used to compare substrate specificity and selectivity of hydroxylation using microbial enzymes and whole-cell biocatalysts. In general, the regioselectivity of reaction was remarkably similar between the different catalysts in that little aromatic or benzylic, but significant aliphatic hydroxylation was observed. However, a more detailed investigation of isolated products showed complementary substrate specificity, functional group compatibility, and regioselectivity of hydroxylation. Substrate specificity and regioselectivity could be further modulated by small changes to the nature of the aromatic side chain, which appears to play an important role in substrate recognition, (C) 1999 Academic Press.
• Applications of intramolecular amidomercuration. 3. Stereoselectivity in intramolecular amidomercuration. Kinetic vs. thermodynamic control
  作者：Kenn E. Harding、Thomas H. Marman

  DOI：10.1021/jo00189a048

  日期：1984.7