(R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate | 1225377-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate
• 英文别名: 3-[(4R)-4-methyl-6-oxocyclohexen-1-yl]propyl acetate
• CAS: 1225377-59-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: IPICZOSXAOSDMQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate 在 咪唑 、 正丁基锂 、 magnesium(II) perchlorate 、 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 copper(l) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 70.81h， 生成 (5R,5′R,6S,6′S,14R,14′R,16R,16′R)-1,1′-dibenzyl-11-(tert-butyldimethylsilyl)-16,16′-dimethyl-1,1′,2,2′,3,3′,4,4′,5,5′,6,6′,7,7′,-15,15′,16,16′,17,17′-icosahydro-10,10′-bi(5,10b-propano1,7-phenanthroline)
  参考文献：
  名称：

  Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

  摘要：

  The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycocline core.

  DOI：

  10.1021/jo400695c
• 作为产物：
  描述：

  (5R)-5-甲基-2-(苯硫基)环己酮 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 82.08h， 生成 (R)-3-(4-methyl-6-oxocyclohex-1-en-1-yl)propyl acetate
  参考文献：
  名称：

  Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2 + 2 + 2] Cycloadditions

  摘要：

  The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycocline core.

  DOI：

  10.1021/jo400695c

文献信息

• Asymmetric Total Synthesis and Structure Elucidation of Huperzine H
  作者：Shinya Shiomi、Kaewsri Wilailak、Wataru Soutome、Hiromitsu Takayama、Mariko Kitajima、Hayato Ishikawa

  DOI：10.1021/acs.joc.1c02672

  日期：2022.3.4

  A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The key steps of this synthesis include a highly diastereoselective Mukaiyama–Michael addition reaction of a pyrrole bearing a silyl enol ether and an intramolecular SN2 cyclization reaction with iodinated pyrrole acting as an effective nucleophile for the formation of

  从市售的 (+)-胡芦巴酮中以 12% 的总产率实现了石杉碱 H 的第一个不对称全合成。该合成的关键步骤包括带有甲硅烷基烯醇醚的吡咯的高度非对映选择性 Mukaiyama-Michael 加成反应和分子内 S N 2 环化反应，碘化吡咯作为形成九元环的有效亲核试剂。结果，建立了石杉碱H的相对和绝对立体化学。
• Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2
  作者：Trevor Johnson、Dionicio Siegel

  DOI：10.1016/j.bmcl.2014.05.060

  日期：2014.8

  The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function as a modulator of pain, complanadine A represents a new chemical probe to selectively interrogate the physiological function of MrgprX2 as well as a potential lead for the development of antihyperalgesics for the treatment of persistent pain. While complanadine A possess agonistic activity the related natural product lycodine, representing half of complanadine A, lacks activity providing a cursory description of the structural requirements for agonistic activity. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-Complanadine A, an Inducer of Neurotrophic Factor Excretion
  作者：Changxia Yuan、Chih-Tsung Chang、Abram Axelrod、Dionicio Siegel

  DOI：10.1021/ja101956x

  日期：2010.5.5

  A total synthesis of the Lycopodium alkaloid (+)-complanadine A is described. Complanadine A has been shown to induce the secretion of neurotrophic factors from 1321N1 cells, promoting the differentiation of PC-12 cells. The use of a simplifying metal mediated [2+2+2] + [2+2+2] sequence using a silyl-substituted diyne and 2 equiv of the corresponding alkyne-nitrile has provided rapid access to the natural product.