N-benzoylcyclohexylalaninal | 126832-06-2

• 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: N-benzoylcyclohexylalaninal
• 英文别名: N-[(2S)-1-cyclohexyl-3-oxopropan-2-yl]benzamide
• CAS: 126832-06-2
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: TUCKNLVZICRRSD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-benzoylcyclohexylalaninal 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-((2S,3S)-O-MTPA-3-hydroxy-1-cyclohexyl-4-pentenyl)benzamide
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r
• 作为产物：
  描述：

  L-环己基丙氨酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 N-benzoylcyclohexylalaninal
  参考文献：
  名称：

  Stereoselective Intramolecular Cyclization of Allyl and Homoallyl Benzamide via π-Allylpalladium Complex Catalyzed by Pd(0)

  摘要：

  The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis of Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same pi-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of beta-amino-alpha-hydroxy acids 1 and gamma-amino-beta-hydroxy acids 2, conveniently protected as oxazoline.

  DOI：

  10.1021/jo991065r

文献信息

• Orally potent human renin inhibitors derived from angiotensinogen transition state: design, synthesis, and mode of interaction
  作者：Kinji Iizuka、Tetsuhide Kamijo、Hiromu Harada、Kenji Akahane、Tetsuhiro Kubota、Hideaki Umeyama、Toshimasa Ishida、Yoshiaki Kiso

  DOI：10.1021/jm00172a005

  日期：1990.10

  (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid, named cyclohexylnorstatine (2a). The optically pure cyclohexylnorstatine was efficiently prepared from Boc-L-cyclohexylalaninol (3), and the stereochemistry of 1a was established by X-ray crystal analysis. The analyses of interaction between 1a and human renin using modeling techniques indicated that (1) the cyclohexyl group of P1 and the naphthyl

  为了合理设计有效的人肾素抑制剂，推导了人肾素复合物和血管紧张素原P1'Val的易裂位点P4 Pro的三维结构。基于这种结构，从血管紧张素原过渡态设计并合成了一种口服有效的人肾素抑制剂（1a）。抑制剂1a包含一个（2R）-3-（吗啉代羰基）-2-（1-萘基甲基）丙酰基残基（P4-P3），具有逆反酰胺键，L-组氨酸和一个新氨基酸（2R， 3S）-3-氨基-4-环己基-2-羟基丁酸，称为环己基去甲他汀（2a）。由Boc-L-环己基丙氨酸（3）有效地制备了光学纯的环己基去甲他汀，并通过X射线晶体分析确定了1a的立体化学。使用建模技术分析1a与人肾素之间的相互作用表明：（1）P1的环己基和P3的萘基分别容纳在较大的疏水性亚位点S1和S3中；（2）将P2 His的咪唑氢键合到Ser-233的侧链OH上，有助于抑制肾素。（3）将环己基去甲他汀异丙酯残基容纳在S1-S1'中。清楚地表明了立体化学在有效和特
• A simple diastereoselective synthesis of cyclohexylnorstatine and allocyclohexylnorstatine.
  作者：Hiromu HARADA、Atsushi TSUBAKI、Tetsuhide KAMIJO、Kinji IIZUKA、Yoshiaki KISO

  DOI：10.1248/cpb.37.2570

  日期：——

  Cyclohexylnorstatine [(2R, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid] (1) and allocyclohexylnorstatine [(2S, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid] (2), designed as key amino acids in renin inhibitors, were synthesized diastereoselectively and simply from Boc-L-phenylalaninol.

  作为肾素抑制剂中的关键氨基酸，环己基鹅掌楸碱[(2R, 3S)-3-氨基-4-环己基-2-羟基丁酸]（1）和异环己基鹅掌楸碱[(2S, 3S)-3-氨基-4-环己基-2-羟基丁酸]（2）由叔丁氧羰基-L-苯丙氨醇非对映选择性地简单合成。
• HARADA, HIROMU;TSUBAKI, ATSUSHI;KAMIJO, TETSUHIDE;IIZUKA, KINJI;KISO, YOS+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2570-2572
  作者：HARADA, HIROMU、TSUBAKI, ATSUSHI、KAMIJO, TETSUHIDE、IIZUKA, KINJI、KISO, YOS+

  DOI：——

  日期：——