(+/-)-Cavernosine

• 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: (+/-)-Cavernosine
• 英文别名: (5R)-5-[(2S)-2-hydroxy-4-(2,6,6-trimethylcyclohexen-1-yl)butan-2-yl]oxolan-2-one
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: TUXSPPHCZDZART-PBHICJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-Cavernosine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 Acetic acid (4R,5S)-4,5-dihydroxy-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-heptyl ester
  参考文献：
  名称：

  Cavernosine, a Novel Ichthyotoxic Terpenoid Lactone from the Sponge Fasciospongia Cavernosa

  摘要：

  AbstractCavernosine, a novel ichthyotoxic terpenoid lactone has been isolated from the sponge Fasciospongia cavernosa. Its structure has been determined by spectral analysis, chemical degradation and correlation with β‐ionone.

  DOI：

  10.1002/bscb.19820910907
• 作为产物：
  描述：

  (R)-5-[(S)-1-Hydroxy-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl]-5H-furan-2-one 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以94%的产率得到(+/-)-Cavernosine
  参考文献：
  名称：

  The synthesis of (±)-cavernosine

  摘要：

  DOI：

  10.1016/s0040-4039(01)83856-9

文献信息

• Synthesis of γ-lactones from intermediate 2-(γ-hydroxyacyl)-imidazoles by N-methylation and base-catalyzed C  C bond cleavage. Application to the synthesis of (±)- cavernosine
  作者：D.Huw Davies、Nicholas A. Haire、Jonathan Hall、Edward H. Smith

  DOI：10.1016/s0040-4020(01)80461-0

  日期：1992.1

  Reaction of the allyl anions of 0-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of alpha- and gamma-attack. Greater steric hindrance in the anion (triisopropylsilyl VS t-butyldimethylsilyl) and in the aldehyde or ketone favours the gamma-products. Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to gamma-lactones. The method was applied to the synthesis of (+/-)-cavernosine.
• JEFFORD, CHARLES W.;JAGGI, DANIELLE;BERNARDINELLI, GERALD;BOUKOUVALAS, JO+, TETRAHEDRON LETT., 28,(1987) N 35, 4041-4044
  作者：JEFFORD, CHARLES W.、JAGGI, DANIELLE、BERNARDINELLI, GERALD、BOUKOUVALAS, JO+

  DOI：——

  日期：——
• Cavernosine, a Novel Ichthyotoxic Terpenoid Lactone from the Sponge Fasciospongia Cavernosa
  作者：J. C. Braekman、D. Daloze、R. Bertau、P. Macedo De Abreu

  DOI：10.1002/bscb.19820910907

  日期：——

  AbstractCavernosine, a novel ichthyotoxic terpenoid lactone has been isolated from the sponge Fasciospongia cavernosa. Its structure has been determined by spectral analysis, chemical degradation and correlation with β‐ionone.
• The synthesis of (±)-cavernosine
  作者：Charles W. Jefford、Danielle Jaggi、Gérald Bernardinelli、John Boukouvalas

  DOI：10.1016/s0040-4039(01)83856-9

  日期：1987.1