(Z,2S)-1-cyclohexyl-6-methylhept-3-en-2-amine | 773041-38-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z,2S)-1-cyclohexyl-6-methylhept-3-en-2-amine
• CAS: 773041-38-6
• 化学式: C₁₄H₂₇N
• 分子量: 209.375
• InChiKey: ISVFOHLAZAGUDV-LBIZBFCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z,2S)-1-cyclohexyl-6-methylhept-3-en-2-amine 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates

  摘要：

  The stereochemistry of the osmium-catalyzed dihydroxylation of a series of chiral allylic amides and carbamates has been studies. The diastereoselectivity of these reactions was found to be dependent upon the solvent and the nitrogen protecting group as well as the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcohols, osmylations of the allylic amides and carbamates in this study were threo selective. Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined.

  DOI：

  10.1016/0957-4166(94)80024-3
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 盐酸 、 potassium tert-butylate 作用下， 以 溶剂黄146 为溶剂， 反应 7.5h， 生成 (Z,2S)-1-cyclohexyl-6-methylhept-3-en-2-amine
  参考文献：
  名称：

  Diastereoselectivity in the osmium-catalyzed dihydroxylation of allylic amides and carbamates

  摘要：

  The stereochemistry of the osmium-catalyzed dihydroxylation of a series of chiral allylic amides and carbamates has been studies. The diastereoselectivity of these reactions was found to be dependent upon the solvent and the nitrogen protecting group as well as the geometry and substitution pattern of the olefin substrate. In contrast to the erythro selectivity observed with allylic alcohols, osmylations of the allylic amides and carbamates in this study were threo selective. Stoichiometric osmylations were consistently more selective than the corresponding catalytic reactions. Control experiments suggest this is due to the presence of a second catalytic cycle based upon an osmium glycolate catalyst which accumulates as the reaction proceeds to completion. Double diastereoselective dihydroxylations of allylic carbamates were also briefly examined.

  DOI：

  10.1016/0957-4166(94)80024-3

文献信息

• Discovery of a Series of Cyclohexylethylamine-Containing Protein Farnesyltransferase Inhibitors Exhibiting Potent Cellular Activity
  作者：Kenneth J. Henry,、James Wasicak、Andrew S. Tasker、Jerome Cohen、Patricia Ewing、Michael Mitten、John J. Larsen、Douglas M. Kalvin、Rolf Swenson、Shi-Chung Ng、Badr Saeed、Sajeev Cherian、Hing Sham、Saul H. Rosenberg

  DOI：10.1021/jm990335v

  日期：1999.11.1

  Sebti-Hamilton type peptidomimetic farnesyltransferase (FTase) inhibitor FTI-276 (1) led to the identification of 6 as a potent enzyme inhibitor (IC(50) of 8 nM) which lacked the problematic thiol residue which had been a common theme in many of the more important FTase inhibitors reported to date. It has previously been disclosed that addition of o-tolyl substitution to FTase inhibitors of the general description

  基于Sebti-Hamilton型拟肽法呢基转移酶（FTase）抑制剂FTI-276（1）的仲苄基胺文库的合成导致6被鉴定为有效的酶抑制剂（IC（50）为8 nM），缺乏有问题的硫醇残基，这是迄今为止报道的许多更重要的FTase抑制剂的常见主题。先前已经公开了在一般描述2的FTase抑制剂中添加邻甲苯基取代对整个细胞中的FTase抑制和Ras异戊二烯基化抑制均具有有益的作用。这两个观察结果的结合使我们合成了7种有效的FTase抑制剂，其在体外抑制FTase的IC（50）为0.16 nM，而在抑制全细胞Ras异戊二烯化时的EC（50）为190 nM。通过经典药物化学对7的修饰导致发现了一系列有效的FTase抑制剂，最终鉴定出25个，其IC（50）为0.20 nM，EC（50）为4.4 nM。在人胰腺癌裸鼠异种移植模型（MiaPaCa细胞）中进行的体内测试显示，口服25剂量可显着减弱这种侵袭性肿瘤细胞系的生长。