1-allylcyclohexanecarboxylic acid tert-butyl ester | 1001379-51-6

• 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-allylcyclohexanecarboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 1-prop-2-enylcyclohexane-1-carboxylate
• CAS: 1001379-51-6
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: ZOHZOCBRHLZVCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allylcyclohexanecarboxylic acid tert-butyl ester 在 臭氧 、 sodium carbonate 、 三甲氧基磷 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 生成 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
• 作为产物：
  描述：

  tert-butyl cyclohexanecarboxylate 、 3-溴丙烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 1-allylcyclohexanecarboxylic 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.