ethyl 2-[di(o-isopropylphenyl)phosphono]propionate | 216519-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[di(o-isopropylphenyl)phosphono]propionate
• 英文别名: Ethyl 2-bis(2-propan-2-ylphenoxy)phosphorylpropanoate
• CAS: 216519-86-7
• 化学式: C₂₃H₃₁O₅P
• 分子量: 418.47
• InChiKey: IQCHKDDWYZGGLH-UHFFFAOYSA-N

物化性质

• 沸点：
  496.9±45.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal 、 ethyl 2-[di(o-isopropylphenyl)phosphono]propionate 在 sodium hydride 作用下， 生成 (Z)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-phenyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Z-Selective Horner−Wadsworth−Emmons Reaction of α-Substituted Ethyl (Diarylphosphono)acetates with Aldehydes¹

  摘要：

  New Horner-Wadsworth-Emmons reagents, ethyl 2-(diarylphosphono)propionates (2), ethyl 2-(diarylphosphono)hexanoates (3), and ethyl 2-(diarylphosphono)-3-methylbutanoates (4) were prepared by alkylation of ethyl (diarylphosphono)acetates. The reaction of 2-4 with various types of aldehydes gave Z-alpha,beta-dialkyl-alpha,beta-unsaturated esters highly selectively. Remarkable temperature-dependent selectivity was observed in the reaction of (PhO)(2)P(O)CHBuCO2Et with octyl aldehyde.

  DOI：

  10.1021/jo981337a
• 作为产物：
  描述：

  ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 、 碘甲烷 在 sodium hydride 作用下， 生成 ethyl 2-[di(o-isopropylphenyl)phosphono]propionate
  参考文献：
  名称：

  Z-Selective Horner−Wadsworth−Emmons Reaction of α-Substituted Ethyl (Diarylphosphono)acetates with Aldehydes¹

  摘要：

  New Horner-Wadsworth-Emmons reagents, ethyl 2-(diarylphosphono)propionates (2), ethyl 2-(diarylphosphono)hexanoates (3), and ethyl 2-(diarylphosphono)-3-methylbutanoates (4) were prepared by alkylation of ethyl (diarylphosphono)acetates. The reaction of 2-4 with various types of aldehydes gave Z-alpha,beta-dialkyl-alpha,beta-unsaturated esters highly selectively. Remarkable temperature-dependent selectivity was observed in the reaction of (PhO)(2)P(O)CHBuCO2Et with octyl aldehyde.

  DOI：

  10.1021/jo981337a

文献信息

• Total Synthesis of (+)-Lasonolide A
  作者：Tomoyuki Yoshimura、Fumika Yakushiji、Shingo Kondo、Xiaofeng Wu、Mitsuru Shindo、Kozo Shishido

  DOI：10.1021/ol0527678

  日期：2006.2.1

  [structure: see text]. An enantiocontrolled total synthesis of (+)-lasonolide A has been accomplished by using the sequential cross metathesis and macrolactonization for the key assembly of the 20-membered polyene macrolide core of the natural product.

  [结构：见文字]。对自然产物的20元多烯大环内酯核的关键组装是通过顺序交叉复分解和大环内酯化来完成的（+）-lasonolide A的对映体控制的全合成。
• Enantioselective Constructionof the C₁-C₁₆Segment of Lasonolide A
  作者：Kozo Shishido、Tatsuya Deba、Fumika Yakushiji、Mitsuru Shindo

  DOI：10.1055/s-2003-40856

  日期：——

  An efficient and enantiocontrolled synthesis of the C1-C16 segment of lasonolide A has been accomplished starting from a readily available optically pure aldehyde.

  从一种容易获得的手性纯醛出发，已经实现了拉索内酯A的C1-C16片段的高效和对映选择性合成。
• Enantioselective Synthesis of (+)-Penostatin E
  作者：Kosuke Fujioka、Hiromasa Yokoe、Atsushi Inoue、Kana Soga、Masayoshi Tsubuki、Kozo Shishido

  DOI：10.1021/jo501225y

  日期：2014.8.15

  The first enantioselective total synthesis of penostatin E has been accomplished. Two highly efficient and diastereoselective reactions, a Hosomi–Sakurai allylation and an intramolecular Pauson–Khand reaction, were utilized for the construction of the basic carbon framework of the target molecule as the key steps. A late-stage introduction of the side chain and a successful base-promoted elimination

  戊抑素E的第一个对映选择性全合成已完成。两个高效且非对映选择性反应，即Hosomi-Sakurai烯丙基化反应和分子内Pauson-Khand反应，被用作构建目标分子基本碳骨架的关键步骤。侧链的后期引入和成功的碱促进的消除反应提供了合成（+）-penostatin E的有效途径。
• Enantioselective Total Synthesis of Macrolide Antitumor Agent (−)-Lasonolide A
  作者：Arun K. Ghosh、Gangli Gong

  DOI：10.1021/ol0701013

  日期：2007.4.1

  [structure: see text] An enantioselective total synthesis of (-)-lasonolide A is described. The upper tetrahydropyran ring was constructed stereoselectively by an intramolecular 1,3-dipolar cycloaddition reaction. The bicyclic isooxazoline led to the tetrahydropyran ring as well as the quaternary stereocenter present in the molecule. The lower tetrahydropyran ring was assembled by a catalytic asymmetric

  [结构：见正文]描述了对-（-）-松香内酯A的对映选择性全合成。通过分子内的1，3-偶极环加成反应立体选择性地构建上四氢吡喃环。双环异恶唑啉导致分子中存在的四氢吡喃环以及四级立体中心。通过催化不对称杂Diels-Alder反应组装低级四氢吡喃环是关键步骤。在此一步反应中，对映选择性地安装了三个立体中心。