(+/-)-3-epi-invictolide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+/-)-3-epi-invictolide
• 英文别名: (3R,5S,6R)-3,5-dimethyl-6-[(2S)-pentan-2-yl]oxan-2-one
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: AZBHSLUQWMFDHU-UKKRHICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基戊醛 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.83h， 生成 (+/-)-3-epi-invictolide
  参考文献：
  名称：

  Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors

  摘要：

  The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (+/-)-2-methylvaleraldehyde (ca.50% overall yield). Intramolecular alkylation (t-BuOK-THF) of 6 or 7 gave a 40:60 mixture of (+/-)-1 and its C(3) epimer. Catalytic hydrogenation of unsaturated lactone 17 afforded (+/-)-1 in 80% yield.

  DOI：

  10.1021/jo00054a014

文献信息

• Obtention de la lactone de prelog-djerassi et d'autres δ-lactones par addition du pentenyltrimethylsilane sur des derives de l'anhydride glutarique
  作者：par Christiane Santelli-Rouvier

  DOI：10.1016/s0040-4039(01)81441-6

  日期：1984.1

  Addition of trans-3-trimethylsilyl-pent-2-ene to derivatives of glutaric anhydride and meso-2,4-dimethylglutaric anhydride leads to precursors of the PRELOG-DJERASSI lactone and related δ-lactones.

  在戊二酸酐和内消旋2,4-二甲基戊二酸酐的衍生物中添加反式-3-三甲基甲硅烷基戊-2-烯可得到PRELOG-DJERASSI内酯和相关的δ-内酯的前体。
• Remote chirality control in 1,2-asymmetric induction: a remarkable difference between the meso- and (±)-isomers of dimethylglutaric hemialdehyde
  作者：Yoshinori Yamamoto、Kensaku Taniguchi、Kazuhiro Maruyama

  DOI：10.1039/c39850001429

  日期：——

  The Lewis acid mediated reaction of the meso-dimethylglutaric hemialdehyde (2) with pent-3-en–2-yltributyltin (1) gave the anti-Cram erythro isomer (4) predominantly, while the reaction of the (±)-isomer (3) produced the Cram erythro derivative (5) preferentially.

  路易斯酸介导的内消旋-二甲基戊二醛（2）与戊-3-烯-2-基三丁基锡（1）的反应主要产生抗Cram赤型异构体（4），而（±）-异构体（3）优先产生Cram erythro衍生物（5）。
• Synthesis and stereochemistry of tetrahydro-3, 5-dimethyl-6-(1)methylbutyl)-2H-pyran-2-one, a component of the queen recognition pheromone of .
  作者：J.R Rocca、J.H Tumlinson、B.M Glancey、C.S Lofgren

  DOI：10.1016/s0040-4039(00)81799-2

  日期：1983.1
• A conformationally rigid acyclic molecule
  作者：Yoshinori Yamamoto、Hisao Nemoto、Rika Kikuchi、Hiromi Komatsu、Ichiro Suzuki

  DOI：10.1021/ja00179a063

  日期：1990.11
• YAMAMOTO, YOSHINORI;TANIGUCHI, KENSAKU;MARUYAMA, KAZUHIRO, J. CHEM. SOC. CHEM. COMMUN., 1985, N 20, 1429-1431
  作者：YAMAMOTO, YOSHINORI、TANIGUCHI, KENSAKU、MARUYAMA, KAZUHIRO

  DOI：——

  日期：——