(3E,8E)-4,8-dimethyl-3,8-decadien-10-olide | 111351-08-7

• 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: (3E,8E)-4,8-dimethyl-3,8-decadien-10-olide
• 英文别名: E,E-suspensolide；SUSPENSOLIDE；(3E,8E)-suspensolide；(4E,9E)-5,9-dimethyl-1-oxacycloundeca-4,9-dien-2-one
• CAS: 111351-08-7
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: RVKDTQISXMBQEU-NSJFVGFPSA-N

物化性质

• 沸点：
  323.5±42.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (3E,8E)-4,8-dimethyl-3,8-decadien-10-olide 生成 2,6-庚二酮
  参考文献：
  名称：

  CHUMAN, T.;SIVINSKI, J.;HEATH, R. R.;CALKINS, C. O.;TUMLINSON, J. H.;BATT+, TETRAHEDRON LETT., 29,(1988) N 50, C. 6561-6564

  摘要：

  DOI：
• 作为产物：
  描述：

  (E,E)-9-Chloro-3,7-dimethyl-1-(tetrahydropyran-2'-yloxy)-2,7-nonadiene 在 氢氧化钾 、 正丁基锂 、 溶剂黄146 、 三苯基膦 、 mercury dichloride 、 mercury(II) oxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 (3E,8E)-4,8-dimethyl-3,8-decadien-10-olide
  参考文献：
  名称：

  Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)

  摘要：

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.

  DOI：

  10.1021/jo00096a029

文献信息

• Diastereoselective Synthesis of (±)-Epianastrephin, (±)-Anastrephin and Analogs Thereof
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US20170305874A1

  公开（公告）日：2017-10-26

  A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R 1 is ethenyl, R 2 and R 3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R 2 is ethenyl, R 1 and R 3 is methyl and n is 1), and analogs thereof (wherein: R 1 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 2 is H, C 1-5 alkyl, C 2-6 alkenyl or C 2-6 alkynyl, R 1 and R 2 together with the carbon atom they are attached form a C 3-6 cycloalkyl ring, R 3 is C 1-5 alkyl and n is 0-2):

  从具有化学式（I）的取代环状酮合成具有化学式（IV）的反式γ-内酯的过程。对（±）-epianastrephin（1）进行立体选择合成（其中：R1为乙烯基，R2和R3为甲基，n为1），（±）-anastrephin（2）进行立体选择合成（其中：R2为乙烯基，R1和R3为甲基，n为1），以及它们的类似物（其中：R1为H，C1-5烷基，C2-6烯基或C2-6炔基，R2为H，C1-5烷基，C2-6烯基或C2-6炔基，R1和R2与它们附着的碳原子一起形成C3-6环烷基环，R3为C1-5烷基，n为0-2）。
• Total synthesis and structure proof of (3E,8E)-suspensolide
  作者：Merle A Battiste、James R Rocca、Roman L Wydra、James H Tumlinson、Tatsuji Chuman

  DOI：10.1016/s0040-4039(00)82398-9

  日期：1988.1

  A new macrolide, E,E-suspensolide (), was prepared in six steps from mesityl oxide. The stereochemistries of intermediate isomers were assigned principally from their 13C NMR spectra. An isomeric macrolide, Z,E-suspensolide (), was also prepared.

  从异亚丙基三醇中分六步制备了一种新的大环内酯类化合物E，E-suspensolide（）。中间体异构体的立体化学主要是由其13 C NMR光谱确定的。还制备了异构体大环内酯，Z，E-悬浮固体（）。
• Suspensolide, a new macrolide component of male caribbean fruit fly( [loew]) volatiles
  作者：T. Chuman、J. Sivinski、R.R. Heath、C.O. Calkins、J.H. Tumlinson、M.A. Battiste、R.L. Wydra、L. Strekowski、J.L. Nation

  DOI：10.1016/s0040-4039(00)82397-7

  日期：1988.1

  A novel macrolide was isolated from volatiles produced by male Caribbean fruit flies and identified as (,)-4,8-dimethyl-3,8-decadien-10-olide, I, on the basis of spectroscopic and chemical evidence, including synthesis.

  根据光谱和化学证据（包括合成），从加勒比雄性果蝇产生的挥发物中分离出一种新型大环内酯，并将其鉴定为（，）-4,8-​​二甲基-3,8-癸二烯-10-内酯。
• Diastereoselective synthesis of (±)-epianastrephin, (±)-anastrephin and analogs thereof
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US10011580B2

  公开（公告）日：2018-07-03

  A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R1 is ethenyl, R2 and R3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R2 is ethenyl, R1 and R3 is methyl and n is 1), and analogs thereof (wherein: R1 is H, C1-5 alkyl, C2-6 alkenyl or C2-6 alkynyl, R2 is H, C1-5 alkyl, C2-6 alkenyl or C2-6 alkynyl, R1 and R2 together with the carbon atom they are attached form a C3-6 cycloalkyl ring, R3 is C1-5 alkyl and n is 0-2):

  一种从具有式(I)的取代环酮合成具有式(IV)的反式融合γ-内酯的工艺。一种非对映选择性合成(±)-epianastrephin (1)（其中：R1 是乙烯基，R2 和 R3 是甲基，n 是 1）、(±)-anastrephin (2)（其中：R2 是乙烯基，R1 和 R3 是甲基，n 是 1）及其类似物（其中：R1为H、C1-5烷基、C2-6烯基或C2-6炔基，R2为H、C1-5烷基、C2-6烯基或C2-6炔基，R1和R2与它们所连接的碳原子一起形成一个C3-6环烷基环，R3为C1-5烷基，n为0-2）：
• Mori, Kenji; Nakazono, Yutaka, Liebigs Annalen der Chemie, 1988, p. 167 - 174
  作者：Mori, Kenji、Nakazono, Yutaka

  DOI：——

  日期：——