methyl 5-oxo-6-heptynoate | 140175-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-oxo-6-heptynoate
• 英文别名: Methyl 5-oxohept-6-ynoate
• CAS: 140175-55-9
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: XJZSNDITHGXLEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-oxo-6-heptynoate 在 四(三苯基膦)钯 咪唑 、 甲醇 、 copper(l) iodide 、 四丁基氟化铵 、 potassium carbonate 、 正丁胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.0h， 生成 白三烯B4
  参考文献：
  名称：

  Use of biological catalysts for the preparation of chiral molecules. 8. Preparation of propargylic alcohols. Application in the total synthesis of leukotriene B4

  摘要：

  Leukotriene B4 (LTB4) (1) was synthesized from two chiral propargylic alcohols 2 and 3 obtained by enantioselective enzymatic hydrolysis and enantiogenic microbial reduction, respectively. Condensation of these two synthons using a rapid and reproducible method not involving a Wittig reaction led to a compound with identical biological activity to that of natural LTB4.

  DOI：

  10.1021/jo00037a044
• 作为产物：
  描述：

  methyl 5-oxo-7-(trimethylsilyl)hept-6-ynoate 在 Sodium tetraborate decahydrate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以92%的产率得到methyl 5-oxo-6-heptynoate
  参考文献：
  名称：

  Use of biological catalysts for the preparation of chiral molecules. 8. Preparation of propargylic alcohols. Application in the total synthesis of leukotriene B4

  摘要：

  Leukotriene B4 (LTB4) (1) was synthesized from two chiral propargylic alcohols 2 and 3 obtained by enantioselective enzymatic hydrolysis and enantiogenic microbial reduction, respectively. Condensation of these two synthons using a rapid and reproducible method not involving a Wittig reaction led to a compound with identical biological activity to that of natural LTB4.

  DOI：

  10.1021/jo00037a044

文献信息

• Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
  作者：Weigang He、Jiadong Hu、Pengyan Wang、Le Chen、Kai Ji、Siyu Yang、Yin Li、Zhilong Xie、Weiqing Xie

  DOI：10.1002/anie.201800567

  日期：2018.3.26

  to alkynones was developed by taking advantage of a chiral N,N′‐dioxide Sc(OTf)3 catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine‐3,3′‐oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(−)‐tubifoline, (−)‐tubifolidine, (−)‐dehydrotubifoline]

  利用手性N，N'-二氧化物Sc（OTf）3催化剂，开发了将对乙酰氨基酚类色胺衍生的高对映选择性串联迈克尔加成吲哚。该反应使对映体富集的螺[吡咯烷-3,3'-羟吲哚]化合物的制备变得容易，这为单萜类吲哚生物碱的合成提供了新的策略。作为一个证明，兜兰生物碱[（-）-tubifoline，（-）-tubifolidine，（-）-dehydrotubifoline]的不对称合成在10-11个步骤中完成。
• Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones
  作者：Tiantian Cong、Huamin Wang、Xiuzheng Li、Hai-Hong Wu、Junliang Zhang

  DOI：10.1039/c9cc04357h

  日期：——

  A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones has been developed, which provides facile access to a series of optically enriched spiro[pyrrolidine-3,3′-oxindole] compounds in good yields with good to excellent enantio- (up to 97% ee) and diastereoselectivities (up to 20 : 1 dr). Mechanistic studies indicate that this tandem reaction proceeds via an intermolecular

  已开发出将手性膦催化的由色胺胺衍生的羟吲哚向迈克尔酮串联迈克尔加成反应的方法，该方法可方便地获得一系列光学富集的螺[吡咯烷-3,3'-羟吲哚]化合物，收率高，对映体性能优良。 （最高97％ee）和非对映选择性（最高20：1 dr）。机理研究表明，该串联反应通过分子间的氮杂-迈克尔/分子内迈克尔加成过程进行。
• An Asymmetric Synthesis of (+)-Isostrychnine Based on Catalytic Asymmetric Tandem Double Michael Addition
  作者：Pengyan Wang、Junhan Chen、Weigang He、Jiacheng Song、Hengqian Song、Hongbo Wei、Weiqing Xie

  DOI：10.1021/acs.orglett.1c01828

  日期：2021.7.16

  Herein, a concise asymmetric synthesis of (+)-isostrychnine is achieved in nine longest-linear steps with a 16% overall yield. The key features of this synthesis include the catalytic asymmetric tandem double Michael addition of a tryptamine-derived oxindole to an alkynone to facilely forge the A/B/C ring framework, a one-pot intramolecular dehydrative condensation/lactamization reaction to efficiently

  在此，(+)-异马钱子碱的简洁不对称合成通过 9 个最长的线性步骤实现，总产率为 16%。该合成的主要特征包括色胺衍生的羟吲哚与炔酮的催化不对称串联双迈克尔加成以轻松形成 A/B/C 环骨架，一锅分子内脱水缩合/内酰胺化反应以有效建立 E /G 环系统和烯丙基二氮烯重排以引入关键烯烃，用于随后的分子内 Heck 反应。
• Stereoselective Synthesis of the 5,5-Difluoro-(12R)- and -(12S)-Leukotrienes B3
  作者：Vijaya Lingam Manthati、Danielle Grée、René Grée

  DOI：10.1002/ejoc.200500200

  日期：2005.9

  The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B3 is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required

  报道了 5,5-二氟-(12R)-和-(12S)-白三烯 B3 的首次合成，其使用灵活且收敛的策略。关键步骤涉及溴二烯酮 4 和炔丙基二氟化物 5 之间的 Sonogashira 偶联；然后是 CBS 类型的减少以建立 (12R) 或 (12S) 立体中心。在受控条件下进行最终的半氢化，提供所需的 E、E、Z 三烯系统。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)