2-methyl-5-(3-oxoprop-1-en-2-yl)cyclopentanecarbaldehyde | 60478-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-methyl-5-(3-oxoprop-1-en-2-yl)cyclopentanecarbaldehyde
• 英文别名: dolichodial cis-trans；Dolichodial；(1R,2S,5S)-2-methyl-5-(3-oxoprop-1-en-2-yl)cyclopentane-1-carbaldehyde
• CAS: 60478-52-6；1198-22-7；5951-57-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: BORBLDJNKYHVJP-FXBDTBDDSA-N

物化性质

• 沸点：
  94-96 °C(Press: 2 Torr)
• 密度：
  1.051±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 盐酸 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 393.25h， 生成 2-methyl-5-(3-oxoprop-1-en-2-yl)cyclopentanecarbaldehyde
  参考文献：
  名称：

  Synthése du (±)-dolichodial trans-cis

  摘要：

  DOI：

  10.1016/0031-9422(80)80215-9

文献信息

• Resolution and Utilization of Ethyl 5-Hydroxycyclopent-1-enecarboxylate: Enantioselective Synthesis of (+)-Mitsugashiwalactone and (-)-Dolichodial
  作者：Takahiro Yamane、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1055/s-1995-3930

  日期：1995.4

  Optically pure ethyl 5-hydroxycyclopent-1-enecarboxylate has been obtained with its acetate in both enantiomeric forms in excellent optical yields from racemic ethyl 5-hydroxycyclopent-1-enecarboxylate by lipase-mediated kinetic resolution. The optically pure (R)-enantiomer thus obtained has been transformed into two naturally occurring iridoid monoterpenes, (+)-mitsugashiwalactone and (-)-dolichodial.

  光学纯的乙基5-羟基环戊-1-烯羧酸酯已通过脂肪酶介导的动力学分辨率，从外消旋乙基5-羟基环戊-1-烯羧酸酯中以优异的光学产率获得其醋酸酯的两种对映异构体。因此获得的光学纯（R）对映体已转化为两种天然存在的紫杉醇单萜，(+)-三叶紫杉醇内酯和(-)-多利克醛。
• Application of Cp₂TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes
  作者：Hina P. A. Khan、Dipendu Das、Tushar Kanti Chakraborty

  DOI：10.1021/acs.joc.8b00752

  日期：2018.6.1

  An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (−)-isoiridomyrmecin, (+)-7-epi-boschnialactone, (+)-teucriumlactone, and (−)-dolichodial in chirally pure forms starting from readily available (+)-β-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cyclization for the construction of the core

  一种简便的手性纯净形式的统一合成（+）-iridomyrmecin，（-）-isoiridomyrmecin，（+）-7- epi -boschnialactone，（+）- teucriumlactone和（-）-dolichodial的统一总合成方法结合了步骤经济性和简便性来描述可利用的（+）-β-香茅烯。亮点包括Ti（III）介导的还原性环氧开放环化反应，用于构建环烯醚酮内酯的核心环戊环[ c ]吡喃骨架，并且对新创建的桥头型立体中心具有完全的非对映选择性。随后的转化有利于短距离访问（+）-四氢内酯和（-）-二齿二元，并正式访问可能的其他虹彩。
• A Divergent Approach to the Diastereoselective Synthesis of Several Ant-Associated Iridoids
  作者：Joel S. Beckett、James D. Beckett、John E. Hofferberth

  DOI：10.1021/ol100077z

  日期：2010.4.2

  The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the Individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.
• [EN] COMPOUNDS WITH SEMIOCHEMICAL PROPERTIES AND BIOSENSORS<br/>[FR] COMPOSÉS AYANT DES PROPRIÉTÉS SÉMIOCHIMIQUES ET BIOCAPTEURS
  申请人：[en]ROTHAMSTED RESEARCH LIMITED

  公开号：WO2022023572A2

  公开（公告）日：2022-02-03

  Provided are a compound of Formula I or Formula IA, a composition comprising a compound of Formula I or Formula IA, uses of the compounds and compositions to modulate insect behaviour and methods for modulating insect behaviour. Also provided are biosensors for detecting an analyte in a sample, uses of the biosensor, and methods for detecting an analyte in a sample.
• Synthése du (±)-dolichodial trans-cis
  作者：C. Beaupin、J.C. Rossi、J.P. Vidal、J.P. Girard、J. Passet

  DOI：10.1016/0031-9422(80)80215-9

  日期：1980.1