(+) dictyopterene C' | 33156-94-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (+) dictyopterene C'
• 英文别名: (+)-Dictyopterene C'；(+)-dictyopterene；(6S)-6-butylcyclohepta-1,4-diene
• CAS: 33156-94-4
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: IRKYSUMPMNRVDS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(trimethylsilyl)hept-1-yn-3-one 在 Lindlar's catalyst 、 bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 咪唑 、 4-二甲氨基吡啶 、 bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 、 (-)-(S)-alpine-borane 、 乙基溴化镁 、 四丁基氟化铵 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.83h， 生成 (+) dictyopterene C'
  参考文献：
  名称：

  Synthesis of (+) dictyopterene a constituent of marine brown algae and (+) dictyopterene C′ by chirality transfer of optically active allylic benzoate with palladium (O) catalyst.

  摘要：

  DOI：

  10.1016/s0040-4039(00)94910-4

文献信息

• Enzymatic hydrolysis of cyclopropanes. Total synthesis of optically pure dictyopterenes a and c'.
  作者：D. Grandjean、P. Pale、J. Chuche

  DOI：10.1016/s0040-4020(01)86378-x

  日期：1991.1

  hydrolysis of cis-1,2-bis(butyryloxymethyl)cyclopropane 3 under optimized conditions gives, in quantitative yield, optically pure cis-(1S,2R)-1-hydroxymethyl-2-butyryloxymethylcyclopropane1. This compound is a versatile cyclopropane synthon as exemplified by the total synthesis of optically pure seaweed pheromones Dictyopterenes A and C'.

  在最佳条件下酶促水解顺-1,2-双（丁酰氧基甲基）环丙烷3可以定量收率得到光学纯的顺-（1S，2R）-1-羟甲基-2-丁酰氧基甲基环丙烷1。该化合物是一种通用的环丙烷合成子，以光学纯的海藻信息素Dictyopterenes A和C'的全合成为例。
• Enantioselective synthesis of dictyopterene C 6R-(-)-butyl-2,5-cycloheptadiene the pheromone of several dictyotales (phaeophyceae)
  作者：Theo Schotten、Wilhelm Boland、Lothar Jaenicke

  DOI：10.1016/s0040-4039(00)84526-8

  日期：——

  R-(-)-Dictyopterene C () is a widespread constituent of many marine brown algae (Phaeophyceae). A highly enantioselective synthesis of i and its enantiomer ent- chromatographic separation of the diastereomeric γ-hydroxyphenylethylamide intermediates and is described.

  R-（-）-Dictyopterene C（）是许多海洋褐藻（Phaeophyceae）的广泛组成部分。I的高度对映选择性合成和其对映体ent-非对映体γ-hydroxyphenylethylamide中间体的色谱分离和进行说明。
• Enantioselective Preparation of 1,3-Cyclohexadiene and 1,4-Cycloheptadiene Derivatives: Synthesis of (+)-Dictyopterene C′
  作者：Morio Asaoka、Katsuhiro Kobayashi、Hisashi Takei

  DOI：10.1246/bcsj.67.1141

  日期：1994.4

  optically active 5-trimethylsilyl-2-cyclohexen-1-one derivatives, the title dienes were synthesized by using silicon-mediated 1,4-elimination as a key step. A straightforward synthesis of the unnatural enantiomer of (−)-dictyopterene C′ utilizing the method was also carried out.

  从光学活性 5-trimethylsilyl-2-cyclohexen-1-one 衍生物开始，通过使用硅介导的 1,4-消除作为关键步骤合成了标题二烯。还使用该方法直接合成了 (-)-二萜烯 C' 的非天然对映异构体。
• cis-Disubstituted Cyclopropanesvia Asymmetric Catalytic Cyclopropenation: Synthesis of Cyclopropyl-dehydroamino Acids and of Dictyopterene C′
  作者：Hassan Imogaï、Gérald Bernardinelli、Christian Gränicher、Mary Moran、Jean-Claude Rossier、Paul Müller

  DOI：10.1002/(sici)1522-2675(19981007)81:10<1754::aid-hlca1754>3.0.co;2-v

  日期：1998.10.7
• Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)
  作者：Georg Pohnert、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)00886-7

  日期：1997.10

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.