1-(2-oxo-ethyl)cyclohexanecarboxylic acid tert-butyl ester | 1001379-53-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(2-oxo-ethyl)cyclohexanecarboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 1-(2-oxoethyl)cyclohexane-1-carboxylate
• CAS: 1001379-53-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: NFZAHBRULVGQSR-UHFFFAOYSA-N

物化性质

• 沸点：
  297.6±13.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-oxo-ethyl)cyclohexanecarboxylic acid tert-butyl ester 、 (4aR,8S,8aR)-8-methyl-6-oxo-octahydroisoquinoline-2-carboxylic acid tert-butyl ester 、 4-(三氟甲基)苯肼 在 硫酸 、 三乙酰氧基硼氢化钠 作用下， 以 1,4-二氧六环 、 水 、 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-[2-((4aR,11R,11aS)-11-methyl-9-trifluoromethyl-2,3,4,4a,5,6,11,11a-octahydropyrido[4,3-b]carbazol-2-yl)ethyl]cyclohexanecarboxylic acid tert-butyl ester 、 tert-butyl 1-[2-[(4aR,5S,11cS)-5-methyl-10-(trifluoromethyl)-1,2,4,4a,5,6,7,11c-octahydropyrido[3,4-c]carbazol-3-yl]ethyl]cyclohexane-1-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of a MCHr1 Antagonist

  摘要：

  [GRAPHICS]Melanin-concentrating hormone (MCH) is implicated in the feeding behavior in mammals affording a potential target to control overeating in people. Compound 1 (AMG 076) has been identified as a potent MCHr1 antagonist for the treatment of obesity. A synthesis suitable for the large-scale preparation of this lead candidate was developed to support preclinical studies. A Robinson annulation of benzylpiperidone and resolution of the desired enone from a mixture of the diastereomers afforded key intermediate 6 after a stereoselective hydrogenation. Subsequent Fischer indole synthesis with hydrazine 5 then provided the advanced intermediate, indole 2. Two complementary reductive amination strategies employing either aldehyde 3 or lactol 4 led to the synthesis of title compound 1.

  DOI：

  10.1021/jo701894v
• 作为产物：
  描述：

  tert-butyl 1-[(E)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclohexyl]but-2-enyl]cyclohexane-1-carboxylate 在 臭氧 、 三甲氧基磷 作用下， 以85%的产率得到1-(2-oxo-ethyl)cyclohexanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of a MCHr1 Antagonist

  摘要：

  [GRAPHICS]Melanin-concentrating hormone (MCH) is implicated in the feeding behavior in mammals affording a potential target to control overeating in people. Compound 1 (AMG 076) has been identified as a potent MCHr1 antagonist for the treatment of obesity. A synthesis suitable for the large-scale preparation of this lead candidate was developed to support preclinical studies. A Robinson annulation of benzylpiperidone and resolution of the desired enone from a mixture of the diastereomers afforded key intermediate 6 after a stereoselective hydrogenation. Subsequent Fischer indole synthesis with hydrazine 5 then provided the advanced intermediate, indole 2. Two complementary reductive amination strategies employing either aldehyde 3 or lactol 4 led to the synthesis of title compound 1.

  DOI：

  10.1021/jo701894v

文献信息

• Stereoselective Synthesis of a MCHr1 Antagonist
  作者：Denise Andersen、Thomas Storz、Pingli Liu、Xin Wang、Leping Li、Pingchen Fan、Xiaoqi Chen、Alan Allgeier、Alain Burgos、Jason Tedrow、Jean Baum、Ying Chen、Rich Crockett、Liang Huang、Rashid Syed、Robert D. Larsen、Mike Martinelli

  DOI：10.1021/jo701894v

  日期：2007.12.1

  [GRAPHICS]Melanin-concentrating hormone (MCH) is implicated in the feeding behavior in mammals affording a potential target to control overeating in people. Compound 1 (AMG 076) has been identified as a potent MCHr1 antagonist for the treatment of obesity. A synthesis suitable for the large-scale preparation of this lead candidate was developed to support preclinical studies. A Robinson annulation of benzylpiperidone and resolution of the desired enone from a mixture of the diastereomers afforded key intermediate 6 after a stereoselective hydrogenation. Subsequent Fischer indole synthesis with hydrazine 5 then provided the advanced intermediate, indole 2. Two complementary reductive amination strategies employing either aldehyde 3 or lactol 4 led to the synthesis of title compound 1.